Merge branch 'develop' into feat/ui-lib

.nvmrc

@@ -1 +1 @@
-20.5.1
+23.7.0

.rubocop.yml

@@ -7,6 +7,7 @@ plugins:
 require:
   - ./rubocop/use_from_email.rb
   - ./rubocop/custom_cop_location.rb
+  - ./rubocop/attachment_download.rb
   - ./rubocop/one_class_per_file.rb
 
 Layout/LineLength:
@@ -41,6 +42,12 @@ Style/SymbolArray:
 Style/OpenStructUse:
   Enabled: false
 
+Chatwoot/AttachmentDownload:
+  Enabled: true
+  Exclude:
+    - 'spec/**/*'
+    - 'test/**/*'
+
 Style/OptionalBooleanParameter:
   Exclude:
     - 'app/services/email_templates/db_resolver_service.rb'
@@ -88,7 +95,7 @@ Metrics/ModuleLength:
 Rails/HelperInstanceVariable:
   Exclude:
     - enterprise/app/helpers/captain/chat_helper.rb
-    - 'enterprise/app/helpers/captain/tool_execution_helper.rb'
+    - enterprise/app/helpers/captain/chat_response_helper.rb
 Rails/ApplicationController:
   Exclude:
     - 'app/controllers/api/v1/widget/messages_controller.rb'

Gemfile

@@ -162,7 +162,7 @@ gem 'working_hours'
 gem 'pg_search'
 
 # Subscriptions, Billing
-gem 'stripe'
+gem 'stripe', '~> 18.0'
 
 ## - helper gems --##
 ## to populate db with sample data
@@ -191,9 +191,10 @@ gem 'reverse_markdown'
 
 gem 'iso-639'
 gem 'ruby-openai'
-gem 'ai-agents', '>= 0.4.3'
+gem 'ai-agents', '>= 0.7.0'
 
 # TODO: Move this gem as a dependency of ai-agents
+gem 'ruby_llm', '>= 1.8.2'
 gem 'ruby_llm-schema'
 
 # OpenTelemetry for LLM observability
@@ -214,7 +215,7 @@ group :production do
 end
 
 group :development do
-  gem 'annotate'
+  gem 'annotaterb'
   gem 'bullet'
   gem 'letter_opener'
   gem 'scss_lint', require: false

Gemfile.lock

@@ -126,11 +126,11 @@ GEM
       jbuilder (~> 2)
       rails (>= 4.2, < 7.2)
       selectize-rails (~> 0.6)
-    ai-agents (0.4.3)
-      ruby_llm (~> 1.3)
-    annotate (3.2.0)
-      activerecord (>= 3.2, < 8.0)
-      rake (>= 10.4, < 14.0)
+    ai-agents (0.7.0)
+      ruby_llm (~> 1.8.2)
+    annotaterb (4.20.0)
+      activerecord (>= 6.0.0)
+      activesupport (>= 6.0.0)
     ast (2.4.3)
     attr_extras (7.1.0)
     audited (5.4.1)
@@ -819,7 +819,7 @@ GEM
     ruby2ruby (2.5.0)
       ruby_parser (~> 3.1)
       sexp_processor (~> 4.6)
-    ruby_llm (1.5.1)
+    ruby_llm (1.8.2)
       base64
       event_stream_parser (~> 1)
       faraday (>= 1.10.0)
@@ -828,7 +828,7 @@ GEM
       faraday-retry (>= 1)
       marcel (~> 1.0)
       zeitwerk (~> 2)
-    ruby_llm-schema (0.1.0)
+    ruby_llm-schema (0.2.5)
     ruby_parser (3.20.0)
       sexp_processor (~> 4.16)
     sass (3.7.4)
@@ -928,7 +928,7 @@ GEM
     squasher (0.7.2)
     stackprof (0.2.25)
     statsd-ruby (1.5.0)
-    stripe (8.5.0)
+    stripe (18.0.1)
     telephone_number (1.4.20)
     test-prof (1.2.1)
     thor (1.4.0)
@@ -1017,8 +1017,8 @@ DEPENDENCIES
   administrate (>= 0.20.1)
   administrate-field-active_storage (>= 1.0.3)
   administrate-field-belongs_to_search (>= 0.9.0)
-  ai-agents (>= 0.4.3)
-  annotate
+  ai-agents (>= 0.7.0)
+  annotaterb
   attr_extras
   audited (~> 5.4, >= 5.4.1)
   aws-actionmailbox-ses (~> 0)
@@ -1119,6 +1119,7 @@ DEPENDENCIES
   rubocop-rails
   rubocop-rspec
   ruby-openai
+  ruby_llm (>= 1.8.2)
   ruby_llm-schema
   scout_apm
   scss_lint
@@ -1139,7 +1140,7 @@ DEPENDENCIES
   spring-watcher-listen
   squasher
   stackprof
-  stripe
+  stripe (~> 18.0)
   telephone_number
   test-prof
   tidewave

app/builders/messages/messenger/message_builder.rb

@@ -9,6 +9,8 @@ class Messages::Messenger::MessageBuilder
     attachment_obj.save!
     attach_file(attachment_obj, attachment_params(attachment)[:remote_file_url]) if attachment_params(attachment)[:remote_file_url]
     fetch_story_link(attachment_obj) if attachment_obj.file_type == 'story_mention'
+    fetch_ig_story_link(attachment_obj) if attachment_obj.file_type == 'ig_story'
+    fetch_ig_post_link(attachment_obj) if attachment_obj.file_type == 'ig_post'
     update_attachment_file_type(attachment_obj)
   end
 
@@ -27,7 +29,7 @@ class Messages::Messenger::MessageBuilder
     file_type = attachment['type'].to_sym
     params = { file_type: file_type, account_id: @message.account_id }
 
-    if [:image, :file, :audio, :video, :share, :story_mention, :ig_reel].include? file_type
+    if [:image, :file, :audio, :video, :share, :story_mention, :ig_reel, :ig_post, :ig_story].include? file_type
       params.merge!(file_type_params(attachment))
     elsif file_type == :location
       params.merge!(location_params(attachment))
@@ -39,9 +41,17 @@ class Messages::Messenger::MessageBuilder
   end
 
   def file_type_params(attachment)
+    # Handle different URL field names for different attachment types
+    url = case attachment['type'].to_sym
+          when :ig_story
+            attachment['payload']['story_media_url']
+          else
+            attachment['payload']['url']
+          end
+
     {
-      external_url: attachment['payload']['url'],
-      remote_file_url: attachment['payload']['url']
+      external_url: url,
+      remote_file_url: url
     }
   end
 
@@ -68,6 +78,21 @@ class Messages::Messenger::MessageBuilder
     message.save!
   end
 
+  def fetch_ig_story_link(attachment)
+    message = attachment.message
+    # For ig_story, we don't have the same API call as story_mention, so we'll set it up similarly but with generic content
+    message.content_attributes[:image_type] = 'ig_story'
+    message.content = I18n.t('conversations.messages.instagram_shared_story_content')
+    message.save!
+  end
+
+  def fetch_ig_post_link(attachment)
+    message = attachment.message
+    message.content_attributes[:image_type] = 'ig_post'
+    message.content = I18n.t('conversations.messages.instagram_shared_post_content')
+    message.save!
+  end
+
   # This is a placeholder method to be overridden by child classes
   def get_story_object_from_source_id(_source_id)
     {}
@@ -76,6 +101,6 @@ class Messages::Messenger::MessageBuilder
   private
 
   def unsupported_file_type?(attachment_type)
-    [:template, :unsupported_type].include? attachment_type.to_sym
+    [:template, :unsupported_type, :ephemeral].include? attachment_type.to_sym
   end
 end

app/javascript/dashboard/api/enterprise/account.js

@@ -23,6 +23,10 @@ class EnterpriseAccountAPI extends ApiClient {
       action_type: action,
     });
   }
+
+  createTopupCheckout(credits) {
+    return axios.post(`${this.url}topup_checkout`, { credits });
+  }
 }
 
 export default new EnterpriseAccountAPI();

app/javascript/dashboard/api/enterprise/specs/account.spec.js

@@ -11,6 +11,8 @@ describe('#enterpriseAccountAPI', () => {
     expect(accountAPI).toHaveProperty('delete');
     expect(accountAPI).toHaveProperty('checkout');
     expect(accountAPI).toHaveProperty('toggleDeletion');
+    expect(accountAPI).toHaveProperty('createTopupCheckout');
+    expect(accountAPI).toHaveProperty('getLimits');
   });
 
   describe('API calls', () => {
@@ -59,5 +61,29 @@ describe('#enterpriseAccountAPI', () => {
         { action_type: 'undelete' }
       );
     });
+
+    it('#createTopupCheckout with credits', () => {
+      accountAPI.createTopupCheckout(1000);
+      expect(axiosMock.post).toHaveBeenCalledWith(
+        '/enterprise/api/v1/topup_checkout',
+        { credits: 1000 }
+      );
+    });
+
+    it('#createTopupCheckout with different credit amounts', () => {
+      const creditAmounts = [1000, 2500, 6000, 12000];
+      creditAmounts.forEach(credits => {
+        accountAPI.createTopupCheckout(credits);
+        expect(axiosMock.post).toHaveBeenCalledWith(
+          '/enterprise/api/v1/topup_checkout',
+          { credits }
+        );
+      });
+    });
+
+    it('#getLimits', () => {
+      accountAPI.getLimits();
+      expect(axiosMock.get).toHaveBeenCalledWith('/enterprise/api/v1/limits');
+    });
   });
 });

app/javascript/dashboard/components-next/Editor/Editor.vue

@@ -19,7 +19,6 @@ const props = defineProps({
   },
   enableVariables: { type: Boolean, default: false },
   enableCannedResponses: { type: Boolean, default: true },
-  enabledMenuOptions: { type: Array, default: () => [] },
   enableCaptainTools: { type: Boolean, default: false },
   signature: { type: String, default: '' },
   allowSignature: { type: Boolean, default: false },
@@ -102,7 +101,6 @@ watch(
         :disabled="disabled"
         :enable-variables="enableVariables"
         :enable-canned-responses="enableCannedResponses"
-        :enabled-menu-options="enabledMenuOptions"
         :enable-captain-tools="enableCaptainTools"
         :signature="signature"
         :allow-signature="allowSignature"
@@ -139,19 +137,6 @@ watch(
 .editor-wrapper {
   ::v-deep {
     .ProseMirror-menubar-wrapper {
-      @apply gap-2 !important;
-
-      .ProseMirror-menubar {
-        @apply bg-transparent dark:bg-transparent w-fit left-1 pt-0 h-5 !top-0 !relative !important;
-
-        .ProseMirror-menuitem {
-          @apply h-5 !important;
-        }
-
-        .ProseMirror-icon {
-          @apply p-1 w-3 h-3 text-n-slate-12 dark:text-n-slate-12 !important;
-        }
-      }
       .ProseMirror.ProseMirror-woot-style {
         p {
           @apply first:mt-0 !important;

app/javascript/dashboard/components-next/HelpCenter/Pages/ArticleEditorPage/ArticleEditor.vue

@@ -172,7 +172,7 @@ const previewArticle = () => {
         @apply mr-0;
 
         .ProseMirror-icon {
-          @apply p-0 mt-1 !mr-0;
+          @apply p-0 mt-0 !mr-0;
 
           svg {
             width: 20px !important;

app/javascript/dashboard/components-next/message/Message.vue

@@ -299,7 +299,12 @@ const componentToRender = computed(() => {
     return DyteBubble;
   }
 
-  if (props.contentAttributes.imageType === 'story_mention') {
+  const instagramSharedTypes = [
+    ATTACHMENT_TYPES.STORY_MENTION,
+    ATTACHMENT_TYPES.IG_STORY,
+    ATTACHMENT_TYPES.IG_POST,
+  ];
+  if (instagramSharedTypes.includes(props.contentAttributes.imageType)) {
     return InstagramStoryBubble;
   }
 
@@ -476,7 +481,7 @@ provideMessageContext({
   <div
     v-if="shouldRenderMessage"
     :id="`message${props.id}`"
-    class="flex w-full message-bubble-container mb-2"
+    class="flex mb-2 w-full message-bubble-container"
     :data-message-id="props.id"
     :class="[
       flexOrientationClass,

app/javascript/dashboard/components-next/message/constants.js

@@ -49,6 +49,8 @@ export const ATTACHMENT_TYPES = {
   STORY_MENTION: 'story_mention',
   CONTACT: 'contact',
   IG_REEL: 'ig_reel',
+  IG_POST: 'ig_post',
+  IG_STORY: 'ig_story',
 };
 
 export const CONTENT_TYPES = {

app/javascript/dashboard/components/widgets/WootWriter/Editor.vue

@@ -26,13 +26,11 @@ import { useAlert } from 'dashboard/composables';
 
 import { BUS_EVENTS } from 'shared/constants/busEvents';
 import { CONVERSATION_EVENTS } from 'dashboard/helper/AnalyticsHelper/events';
-import {
-  MESSAGE_EDITOR_MENU_OPTIONS,
-  MESSAGE_EDITOR_IMAGE_RESIZES,
-} from 'dashboard/constants/editor';
+import { MESSAGE_EDITOR_IMAGE_RESIZES } from 'dashboard/constants/editor';
 
 import {
   messageSchema,
+  buildMessageSchema,
   buildEditor,
   EditorView,
   MessageMarkdownTransformer,
@@ -53,6 +51,9 @@ import {
   removeSignature as removeSignatureHelper,
   scrollCursorIntoView,
   setURLWithQueryAndSize,
+  getFormattingForEditor,
+  getSelectionCoords,
+  calculateMenuPosition,
 } from 'dashboard/helper/editorHelper';
 import {
   hasPressedEnterAndNotCmdOrShift,
@@ -75,7 +76,6 @@ const props = defineProps({
   enableCannedResponses: { type: Boolean, default: true },
   enableCaptainTools: { type: Boolean, default: false },
   variables: { type: Object, default: () => ({}) },
-  enabledMenuOptions: { type: Array, default: () => [] },
   signature: { type: String, default: '' },
   // allowSignature is a kill switch, ensuring no signature methods
   // are triggered except when this flag is true
@@ -103,22 +103,34 @@ const { t } = useI18n();
 
 const TYPING_INDICATOR_IDLE_TIME = 4000;
 const MAXIMUM_FILE_UPLOAD_SIZE = 4; // in MB
+const DEFAULT_FORMATTING = 'Context::Default';
 
-const createState = (
-  content,
-  placeholder,
-  plugins = [],
-  methods = {},
-  enabledMenuOptions = []
-) => {
+const editorSchema = computed(() => {
+  if (!props.channelType) return messageSchema;
+
+  const formatType = props.isPrivate ? DEFAULT_FORMATTING : props.channelType;
+  const formatting = getFormattingForEditor(formatType);
+  return buildMessageSchema(formatting.marks, formatting.nodes);
+});
+
+const editorMenuOptions = computed(() => {
+  const formatType = props.isPrivate
+    ? DEFAULT_FORMATTING
+    : props.channelType || DEFAULT_FORMATTING;
+  const formatting = getFormattingForEditor(formatType);
+  return formatting.menu;
+});
+
+const createState = (content, placeholder, plugins = [], methods = {}) => {
+  const schema = editorSchema.value;
   return EditorState.create({
-    doc: new MessageMarkdownTransformer(messageSchema).parse(content),
+    doc: new MessageMarkdownTransformer(schema).parse(content),
     plugins: buildEditor({
-      schema: messageSchema,
+      schema,
       placeholder,
       methods,
       plugins,
-      enabledMenuOptions,
+      enabledMenuOptions: editorMenuOptions.value,
     }),
   });
 };
@@ -153,6 +165,8 @@ const range = ref(null);
 const isImageNodeSelected = ref(false);
 const toolbarPosition = ref({ top: 0, left: 0 });
 const selectedImageNode = ref(null);
+const isTextSelected = ref(false); // Tracks text selection and prevents unnecessary re-renders on mouse selection
+const showSelectionMenu = ref(false);
 const sizes = MESSAGE_EDITOR_IMAGE_RESIZES;
 
 // element ref
@@ -174,16 +188,6 @@ const shouldShowCannedResponses = computed(() => {
   );
 });
 
-const editorMenuOptions = computed(() => {
-  // eslint-disable-next-line no-underscore-dangle
-  if (window.__WOOT_ISOLATED_SHELL__) {
-    return [];
-  }
-  return props.enabledMenuOptions.length
-    ? props.enabledMenuOptions
-    : MESSAGE_EDITOR_MENU_OPTIONS;
-});
-
 function createSuggestionPlugin({
   trigger,
   minChars = 0,
@@ -404,6 +408,38 @@ function setToolbarPosition() {
   };
 }
 
+function setMenubarPosition({ selection } = {}) {
+  const wrapper = editorRoot.value;
+  if (!selection || !wrapper) return;
+
+  const rect = wrapper.getBoundingClientRect();
+  const isRtl = getComputedStyle(wrapper).direction === 'rtl';
+
+  // Calculate coords and final position
+  const coords = getSelectionCoords(editorView, selection, rect);
+  const { left, top, width } = calculateMenuPosition(coords, rect, isRtl);
+
+  wrapper.style.setProperty('--selection-left', `${left}px`);
+  wrapper.style.setProperty(
+    '--selection-right',
+    `${rect.width - left - width}px`
+  );
+  wrapper.style.setProperty('--selection-top', `${top}px`);
+}
+
+function checkSelection(editorState) {
+  showSelectionMenu.value = false;
+  const hasSelection = editorState.selection.from !== editorState.selection.to;
+  if (hasSelection === isTextSelected.value) return;
+
+  isTextSelected.value = hasSelection;
+  const wrapper = editorRoot.value;
+  if (!wrapper) return;
+
+  wrapper.classList.toggle('has-selection', hasSelection);
+  if (hasSelection) setMenubarPosition(editorState);
+}
+
 function setURLWithQueryAndImageSize(size) {
   if (!props.showImageResizeToolbar) {
     return;
@@ -537,7 +573,9 @@ async function insertNodeIntoEditor(node, from = 0, to = 0) {
 
 function insertContentIntoEditor(content, defaultFrom = 0) {
   const from = defaultFrom || editorView.state.selection.from || 0;
-  let node = new MessageMarkdownTransformer(messageSchema).parse(content);
+  // Use the editor's current schema to ensure compatibility with buildMessageSchema
+  const currentSchema = editorView.state.schema;
+  let node = new MessageMarkdownTransformer(currentSchema).parse(content);
 
   insertNodeIntoEditor(node, from, undefined);
 }
@@ -604,6 +642,7 @@ function createEditorView() {
       if (tx.docChanged) {
         emitOnChange();
       }
+      checkSelection(state);
     },
     handleDOMEvents: {
       keyup: () => {
@@ -769,7 +808,7 @@ useEmitter(BUS_EVENTS.INSERT_INTO_RICH_EDITOR, insertContentIntoEditor);
 @import '@chatwoot/prosemirror-schema/src/styles/base.scss';
 
 .ProseMirror-menubar-wrapper {
-  @apply flex flex-col;
+  @apply flex flex-col gap-3;
 
   .ProseMirror-menubar:empty {
     display: none;
@@ -777,11 +816,29 @@ useEmitter(BUS_EVENTS.INSERT_INTO_RICH_EDITOR, insertContentIntoEditor);
 
   .ProseMirror-menubar {
     min-height: 1.25rem !important;
-    @apply -ml-2.5 pb-0 bg-transparent text-n-slate-11;
+    @apply items-center gap-4 flex pb-0 bg-transparent text-n-slate-11 relative ltr:-left-[3px] rtl:-right-[3px];
 
     .ProseMirror-menu-active {
-      @apply bg-n-slate-5 dark:bg-n-solid-3;
+      @apply bg-n-slate-5 dark:bg-n-solid-3 !important;
     }
+
+    .ProseMirror-menuitem {
+      @apply mr-0 size-4 flex items-center justify-center;
+
+      .ProseMirror-icon {
+        @apply size-4 flex items-center justify-center flex-shrink-0;
+
+        svg {
+          @apply size-full;
+        }
+      }
+    }
+  }
+
+  .ProseMirror-menubar:not(:has(*)) {
+    max-height: none !important;
+    min-height: 0 !important;
+    padding: 0 !important;
   }
 
   > .ProseMirror {
@@ -872,4 +929,53 @@ useEmitter(BUS_EVENTS.INSERT_INTO_RICH_EDITOR, insertContentIntoEditor);
 .editor-warning__message {
   @apply text-n-ruby-9 dark:text-n-ruby-9 font-normal text-sm pt-1 pb-0 px-0;
 }
+
+// Float editor menu
+.popover-prosemirror-menu {
+  position: relative;
+
+  .ProseMirror p:last-child {
+    margin-bottom: 10px !important;
+  }
+
+  .ProseMirror-menubar {
+    display: none; // Hide by default
+  }
+
+  &.has-selection {
+    // Hide menu completely when it has no items
+    .ProseMirror-menubar:not(:has(*)) {
+      display: none !important;
+    }
+
+    .ProseMirror-menubar {
+      @apply rounded-lg !px-3 !py-1.5 z-50 bg-n-background items-center gap-4 ml-0 mb-0 shadow-md outline outline-1 outline-n-weak;
+      display: flex;
+      width: fit-content !important;
+      position: absolute !important;
+
+      // Default/LTR: position from left
+      top: var(--selection-top);
+      left: var(--selection-left);
+
+      // RTL: position from right instead
+      [dir='rtl'] & {
+        left: auto;
+        right: var(--selection-right);
+      }
+
+      .ProseMirror-menuitem {
+        @apply mr-0 size-4 flex items-center;
+
+        .ProseMirror-icon {
+          @apply p-0.5 flex-shrink-0;
+        }
+      }
+
+      .ProseMirror-menu-active {
+        @apply bg-n-slate-3;
+      }
+    }
+  }
+}
 </style>

app/javascript/dashboard/components/widgets/WootWriter/ReplyBottomPanel.vue

@@ -78,10 +78,6 @@ export default {
       type: Boolean,
       default: false,
     },
-    showEditorToggle: {
-      type: Boolean,
-      default: false,
-    },
     isOnPrivateNote: {
       type: Boolean,
       default: false,
@@ -136,7 +132,6 @@ export default {
   emits: [
     'replaceText',
     'toggleInsertArticle',
-    'toggleEditor',
     'selectWhatsappTemplate',
     'selectContentTemplate',
     'toggleQuotedReply',
@@ -357,7 +352,25 @@ export default {
         />
       </template>
       <NextButton
-        v-if="allowSignature && showMessageSignatureButton"
+        v-if="showAudioRecorderButton"
+        v-tooltip.top-end="$t('CONVERSATION.REPLYBOX.TIP_AUDIORECORDER_ICON')"
+        :icon="!isRecordingAudio ? 'i-ph-microphone' : 'i-ph-microphone-slash'"
+        slate
+        faded
+        sm
+        @click="toggleAudioRecorder"
+      />
+      <NextButton
+        v-if="showAudioPlayStopButton"
+        :icon="audioRecorderPlayStopIcon"
+        slate
+        faded
+        sm
+        :label="recordingAudioDurationText"
+        @click="toggleAudioRecorderPlayPause"
+      />
+      <NextButton
+        v-if="showMessageSignatureButton"
         v-tooltip.top-end="signatureToggleTooltip"
         icon="i-ph-signature"
         slate

app/javascript/dashboard/components/widgets/conversation/ReplyBox.vue

@@ -7,9 +7,7 @@ import { useTrack } from 'dashboard/composables';
 import keyboardEventListenerMixins from 'shared/mixins/keyboardEventListenerMixins';
 import { FEATURE_FLAGS } from 'dashboard/featureFlags';
 
-import CannedResponse from './CannedResponse.vue';
 import ReplyToMessage from './ReplyToMessage.vue';
-import ResizableTextArea from 'shared/components/ResizableTextArea.vue';
 import AttachmentPreview from 'dashboard/components/widgets/AttachmentsPreview.vue';
 import ReplyTopPanel from 'dashboard/components/widgets/WootWriter/ReplyTopPanel.vue';
 import ReplyEmailHead from './ReplyEmailHead.vue';
@@ -45,8 +43,6 @@ import fileUploadMixin from 'dashboard/mixins/fileUploadMixin';
 import {
   appendSignature,
   removeSignature,
-  replaceSignature,
-  extractTextFromMarkdown,
 } from 'dashboard/helper/editorHelper';
 
 import { LOCAL_STORAGE_KEYS } from 'dashboard/constants/localStorage';
@@ -61,7 +57,6 @@ export default {
     ArticleSearchPopover,
     AttachmentPreview,
     AudioRecorder,
-    CannedResponse,
     ReplyBoxBanner,
     EmojiInput,
     MessageSignatureMissingAlert,
@@ -69,7 +64,6 @@ export default {
     ReplyEmailHead,
     ReplyToMessage,
     ReplyTopPanel,
-    ResizableTextArea,
     ContentTemplates,
     WhatsappTemplates,
     WootMessageEditor,
@@ -86,7 +80,6 @@ export default {
   setup() {
     const {
       uiSettings,
-      updateUISettings,
       isEditorHotKeyEnabled,
       fetchSignatureFlagFromUISettings,
       setQuotedReplyFlagForInbox,
@@ -97,7 +90,6 @@ export default {
 
     return {
       uiSettings,
-      updateUISettings,
       isEditorHotKeyEnabled,
       fetchSignatureFlagFromUISettings,
       setQuotedReplyFlagForInbox,
@@ -115,10 +107,7 @@ export default {
       isRecordingAudio: false,
       recordingAudioState: '',
       recordingAudioDurationText: '',
-      isUploading: false,
       replyType: REPLY_EDITOR_MODES.REPLY,
-      mentionSearchKey: '',
-      hasSlashCommand: false,
       bccEmails: '',
       ccEmails: '',
       toEmails: '',
@@ -159,20 +148,6 @@ export default {
         !this.is360DialogWhatsAppChannel
       );
     },
-    showRichContentEditor() {
-      if (this.isOnPrivateNote || this.isRichEditorEnabled) {
-        return true;
-      }
-
-      if (this.isAPIInbox) {
-        const {
-          display_rich_content_editor: displayRichContentEditor = false,
-        } = this.uiSettings;
-        return displayRichContentEditor;
-      }
-
-      return false;
-    },
     showWhatsappTemplates() {
       // We support templates for API channels if someone updates templates manually via API
       // That's why we don't explicitly check for channel type here
@@ -300,9 +275,6 @@ export default {
     hasAttachments() {
       return this.attachedFiles.length;
     },
-    isRichEditorEnabled() {
-      return this.isAWebWidgetInbox || this.isAnEmailChannel;
-    },
     showAudioRecorder() {
       return !this.isOnPrivateNote && this.showFileUpload;
     },
@@ -342,21 +314,11 @@ export default {
       return !this.isPrivate && this.sendWithSignature;
     },
     isSignatureAvailable() {
-      return !!this.signatureToApply;
+      return !!this.messageSignature;
     },
     sendWithSignature() {
       return this.fetchSignatureFlagFromUISettings(this.channelType);
     },
-    editorMessageKey() {
-      const { editor_message_key: isEnabled } = this.uiSettings;
-      return isEnabled;
-    },
-    commandPlusEnterToSendEnabled() {
-      return this.editorMessageKey === 'cmd_enter';
-    },
-    enterToSendEnabled() {
-      return this.editorMessageKey === 'enter';
-    },
     conversationId() {
       return this.currentChat.id;
     },
@@ -383,12 +345,6 @@ export default {
       });
       return variables;
     },
-    // ensure that the signature is plain text depending on `showRichContentEditor`
-    signatureToApply() {
-      return this.showRichContentEditor
-        ? this.messageSignature
-        : extractTextFromMarkdown(this.messageSignature);
-    },
     connectedPortalSlug() {
       const { help_center: portal = {} } = this.inbox;
       const { slug = '' } = portal;
@@ -481,25 +437,7 @@ export default {
         this.resetRecorderAndClearAttachments();
       }
     },
-    message(updatedMessage) {
-      // Check if the message starts with a slash.
-      const bodyWithoutSignature = removeSignature(
-        updatedMessage,
-        this.signatureToApply
-      );
-      const startsWithSlash = bodyWithoutSignature.startsWith('/');
-
-      // Determine if the user is potentially typing a slash command.
-      // This is true if the message starts with a slash and the rich content editor is not active.
-      this.hasSlashCommand = startsWithSlash && !this.showRichContentEditor;
-      this.showMentions = this.hasSlashCommand;
-
-      // If a slash command is active, extract the command text after the slash.
-      // If not, reset the mentionSearchKey.
-      this.mentionSearchKey = this.hasSlashCommand
-        ? bodyWithoutSignature.substring(1)
-        : '';
-
+    message() {
       // Autosave the current message draft.
       this.doAutoSaveDraft();
     },
@@ -512,7 +450,7 @@ export default {
   mounted() {
     this.getFromDraft();
     // Don't use the keyboard listener mixin here as the events here are supposed to be
-    // working even if input/textarea is focussed.
+    // working even if the editor is focussed.
     document.addEventListener('paste', this.onPaste);
     document.addEventListener('keydown', this.handleKeyEvents);
     this.setCCAndToEmailsFromLastChat();
@@ -549,45 +487,17 @@ export default {
   methods: {
     handleInsert(article) {
       const { url, title } = article;
-      if (this.isRichEditorEnabled) {
-        // Removing empty lines from the title
-        const lines = title.split('\n');
-        const nonEmptyLines = lines.filter(line => line.trim() !== '');
-        const filteredMarkdown = nonEmptyLines.join(' ');
-        emitter.emit(
-          BUS_EVENTS.INSERT_INTO_RICH_EDITOR,
-          `[${filteredMarkdown}](${url})`
-        );
-      } else {
-        this.addIntoEditor(
-          `${this.$t('CONVERSATION.REPLYBOX.INSERT_READ_MORE')} ${url}`
-        );
-      }
+      // Removing empty lines from the title
+      const lines = title.split('\n');
+      const nonEmptyLines = lines.filter(line => line.trim() !== '');
+      const filteredMarkdown = nonEmptyLines.join(' ');
+      emitter.emit(
+        BUS_EVENTS.INSERT_INTO_RICH_EDITOR,
+        `[${filteredMarkdown}](${url})`
+      );
 
       useTrack(CONVERSATION_EVENTS.INSERT_ARTICLE_LINK);
     },
-    toggleRichContentEditor() {
-      this.updateUISettings({
-        display_rich_content_editor: !this.showRichContentEditor,
-      });
-
-      const plainTextSignature = extractTextFromMarkdown(this.messageSignature);
-
-      if (!this.showRichContentEditor && this.messageSignature) {
-        // remove the old signature -> extract text from markdown -> attach new signature
-        let message = removeSignature(this.message, this.messageSignature);
-        message = extractTextFromMarkdown(message);
-        message = appendSignature(message, plainTextSignature);
-
-        this.message = message;
-      } else {
-        this.message = replaceSignature(
-          this.message,
-          plainTextSignature,
-          this.messageSignature
-        );
-      }
-    },
     toggleQuotedReply() {
       if (!this.isAnEmailChannel) {
         return;
@@ -655,8 +565,8 @@ export default {
       }
 
       return this.sendWithSignature
-        ? appendSignature(message, this.signatureToApply)
-        : removeSignature(message, this.signatureToApply);
+        ? appendSignature(message, this.messageSignature)
+        : removeSignature(message, this.messageSignature);
     },
     removeFromDraft() {
       if (this.conversationIdByRoute) {
@@ -672,7 +582,6 @@ export default {
         Escape: {
           action: () => {
             this.hideEmojiPicker();
-            this.hideMentions();
           },
           allowOnFocusedInput: true,
         },
@@ -715,9 +624,6 @@ export default {
     },
     onPaste(e) {
       const data = e.clipboardData.files;
-      if (!this.showRichContentEditor && data.length !== 0) {
-        this.$refs.messageInput.$el.blur();
-      }
       if (!data.length || !data[0]) {
         return;
       }
@@ -851,7 +757,7 @@ export default {
         // if signature is enabled, append it to the message
         // appendSignature ensures that the signature is not duplicated
         // so we don't need to check if the signature is already present
-        message = appendSignature(message, this.signatureToApply);
+        message = appendSignature(message, this.messageSignature);
       }
 
       const updatedMessage = replaceVariablesInMessage({
@@ -875,40 +781,22 @@ export default {
       });
       if (canReply || this.isAWhatsAppChannel || this.isAPIInbox)
         this.replyType = mode;
-      if (this.showRichContentEditor) {
-        if (this.isRecordingAudio) {
-          this.toggleAudioRecorder();
-        }
-        return;
+      if (this.isRecordingAudio) {
+        this.toggleAudioRecorder();
       }
-      this.$nextTick(() => this.$refs.messageInput.focus());
     },
     clearEditorSelection() {
       this.updateEditorSelectionWith = '';
     },
-    insertIntoTextEditor(text, selectionStart, selectionEnd) {
-      const { message } = this;
-      const newMessage =
-        message.slice(0, selectionStart) +
-        text +
-        message.slice(selectionEnd, message.length);
-      this.message = newMessage;
-    },
     addIntoEditor(content) {
-      if (this.showRichContentEditor) {
-        this.updateEditorSelectionWith = content;
-        this.onFocus();
-      }
-      if (!this.showRichContentEditor) {
-        const { selectionStart, selectionEnd } = this.$refs.messageInput.$el;
-        this.insertIntoTextEditor(content, selectionStart, selectionEnd);
-      }
+      this.updateEditorSelectionWith = content;
+      this.onFocus();
     },
     clearMessage() {
       this.message = '';
       if (this.sendWithSignature && !this.isPrivate) {
         // if signature is enabled, append it to the message
-        this.message = appendSignature(this.message, this.signatureToApply);
+        this.message = appendSignature(this.message, this.messageSignature);
       }
       this.attachedFiles = [];
       this.isRecordingAudio = false;
@@ -926,19 +814,15 @@ export default {
     },
     toggleAudioRecorder() {
       this.isRecordingAudio = !this.isRecordingAudio;
-      this.isRecorderAudioStopped = !this.isRecordingAudio;
       if (!this.isRecordingAudio) {
         this.resetAudioRecorderInput();
       }
     },
     toggleAudioRecorderPlayPause() {
-      if (!this.isRecordingAudio) {
-        return;
-      }
-      if (!this.isRecorderAudioStopped) {
-        this.isRecorderAudioStopped = true;
+      if (!this.$refs.audioRecorderInput) return;
+      if (!this.recordingAudioState) {
         this.$refs.audioRecorderInput.stopRecording();
-      } else if (this.isRecorderAudioStopped) {
+      } else {
         this.$refs.audioRecorderInput.playPause();
       }
     },
@@ -947,9 +831,6 @@ export default {
         this.toggleEmojiPicker();
       }
     },
-    hideMentions() {
-      this.showMentions = false;
-    },
     onTypingOn() {
       this.toggleTyping('on');
     },
@@ -1196,13 +1077,6 @@ export default {
         :message="inReplyTo"
         @dismiss="resetReplyToMessage"
       />
-      <CannedResponse
-        v-if="showMentions && hasSlashCommand"
-        v-on-clickaway="hideMentions"
-        class="normal-editor__canned-box"
-        :search-key="mentionSearchKey"
-        @replace="replaceText"
-      />
       <EmojiInput
         v-if="showEmojiPicker"
         v-on-clickaway="hideEmojiPicker"
@@ -1226,33 +1100,17 @@ export default {
         @play="recordingAudioState = 'playing'"
         @pause="recordingAudioState = 'paused'"
       />
-      <ResizableTextArea
-        v-else-if="!showRichContentEditor"
-        ref="messageInput"
-        v-model="message"
-        class="rounded-none input"
-        :placeholder="messagePlaceHolder"
-        :min-height="4"
-        :signature="signatureToApply"
-        allow-signature
-        :send-with-signature="sendWithSignature"
-        @typing-off="onTypingOff"
-        @typing-on="onTypingOn"
-        @focus="onFocus"
-        @blur="onBlur"
-      />
       <WootMessageEditor
-        v-else
         v-model="message"
         :editor-id="editorStateId"
-        class="input"
+        class="input popover-prosemirror-menu"
         :is-private="isOnPrivateNote"
         :placeholder="messagePlaceHolder"
         :update-selection-with="updateEditorSelectionWith"
         :min-height="4"
         enable-variables
         :variables="messageVariables"
-        :signature="signatureToApply"
+        :signature="messageSignature"
         allow-signature
         :channel-type="channelType"
         @typing-off="onTypingOff"
@@ -1302,7 +1160,6 @@ export default {
       :recording-audio-state="recordingAudioState"
       :send-button-text="replyButtonLabel"
       :show-audio-recorder="showAudioRecorder"
-      :show-editor-toggle="isAPIInbox && !isOnPrivateNote"
       :show-emoji-picker="showEmojiPicker"
       :show-file-upload="showFileUpload"
       :show-quoted-reply-toggle="shouldShowQuotedReplyToggle"
@@ -1321,7 +1178,6 @@ export default {
       allow-file-upload
       @select-whatsapp-template="openWhatsappTemplateModal"
       @select-content-template="openContentTemplateModal"
-      @toggle-editor="toggleRichContentEditor"
       @replace-text="replaceText"
       @toggle-insert-article="toggleInsertArticle"
       @toggle-quoted-reply="toggleQuotedReply"
@@ -1375,10 +1231,6 @@ export default {
 
 .reply-box__top {
   @apply relative py-0 px-4 -mt-px;
-
-  textarea {
-    @apply shadow-none outline-none border-transparent bg-transparent m-0 max-h-60 min-h-[3rem] pt-4 pb-0 px-0 resize-none;
-  }
 }
 
 .emoji-dialog {
@@ -1398,9 +1250,4 @@ export default {
     @apply ltr:left-1 rtl:right-1 -bottom-2;
   }
 }
-
-.normal-editor__canned-box {
-  width: calc(100% - 2 * 1rem);
-  left: 1rem;
-}
 </style>

app/javascript/dashboard/composables/useCaptain.js

@@ -1,5 +1,5 @@
 import { computed } from 'vue';
-import { useStore } from 'dashboard/composables/store.js';
+import { useMapGetter, useStore } from 'dashboard/composables/store.js';
 import { useAccount } from 'dashboard/composables/useAccount';
 import { useConfig } from 'dashboard/composables/useConfig';
 import { useCamelCase } from 'dashboard/composables/useTransformKeys';
@@ -9,6 +9,7 @@ export function useCaptain() {
   const store = useStore();
   const { isCloudFeatureEnabled, currentAccount } = useAccount();
   const { isEnterprise } = useConfig();
+  const uiFlags = useMapGetter('accounts/getUIFlags');
 
   const captainEnabled = computed(() => {
     return isCloudFeatureEnabled(FEATURE_FLAGS.CAPTAIN);
@@ -34,6 +35,8 @@ export function useCaptain() {
     return null;
   });
 
+  const isFetchingLimits = computed(() => uiFlags.value.isFetchingLimits);
+
   const fetchLimits = () => {
     if (isEnterprise) {
       store.dispatch('accounts/limits');
@@ -46,5 +49,6 @@ export function useCaptain() {
     documentLimits,
     responseLimits,
     fetchLimits,
+    isFetchingLimits,
   };
 }

app/javascript/dashboard/constants/editor.js

@@ -1,23 +1,143 @@
-export const MESSAGE_EDITOR_MENU_OPTIONS = [
-  'strong',
-  'em',
-  'link',
-  'undo',
-  'redo',
-  'bulletList',
-  'orderedList',
-  'code',
-];
-
-export const MESSAGE_SIGNATURE_EDITOR_MENU_OPTIONS = [
-  'strong',
-  'em',
-  'link',
-  'undo',
-  'redo',
-  'imageUpload',
-];
+// Formatting rules for different contexts (channels and special contexts)
+// marks: inline formatting (strong, em, code, link, strike)
+// nodes: block structures (bulletList, orderedList, codeBlock, blockquote)
+export const FORMATTING = {
+  // Channel formatting
+  'Channel::Email': {
+    marks: ['strong', 'em', 'code', 'link'],
+    nodes: ['bulletList', 'orderedList', 'codeBlock', 'blockquote'],
+    menu: [
+      'strong',
+      'em',
+      'code',
+      'link',
+      'bulletList',
+      'orderedList',
+      'undo',
+      'redo',
+    ],
+  },
+  'Channel::WebWidget': {
+    marks: ['strong', 'em', 'code', 'link', 'strike'],
+    nodes: ['bulletList', 'orderedList', 'codeBlock', 'blockquote'],
+    menu: [
+      'strong',
+      'em',
+      'code',
+      'link',
+      'strike',
+      'bulletList',
+      'orderedList',
+      'undo',
+      'redo',
+    ],
+  },
+  'Channel::Api': {
+    marks: ['strong', 'em'],
+    nodes: [],
+    menu: ['strong', 'em', 'undo', 'redo'],
+  },
+  'Channel::FacebookPage': {
+    marks: ['strong', 'em', 'code', 'strike'],
+    nodes: ['bulletList', 'orderedList', 'codeBlock'],
+    menu: [
+      'strong',
+      'em',
+      'code',
+      'strike',
+      'bulletList',
+      'orderedList',
+      'undo',
+      'redo',
+    ],
+  },
+  'Channel::TwitterProfile': {
+    marks: [],
+    nodes: [],
+    menu: [],
+  },
+  'Channel::TwilioSms': {
+    marks: [],
+    nodes: [],
+    menu: [],
+  },
+  'Channel::Sms': {
+    marks: [],
+    nodes: [],
+    menu: [],
+  },
+  'Channel::Whatsapp': {
+    marks: ['strong', 'em', 'code', 'strike'],
+    nodes: ['bulletList', 'orderedList', 'codeBlock'],
+    menu: [
+      'strong',
+      'em',
+      'code',
+      'strike',
+      'bulletList',
+      'orderedList',
+      'undo',
+      'redo',
+    ],
+  },
+  'Channel::Line': {
+    marks: ['strong', 'em', 'code', 'strike'],
+    nodes: ['codeBlock'],
+    menu: ['strong', 'em', 'code', 'strike', 'undo', 'redo'],
+  },
+  'Channel::Telegram': {
+    marks: ['strong', 'em', 'link', 'code'],
+    nodes: [],
+    menu: ['strong', 'em', 'link', 'code', 'undo', 'redo'],
+  },
+  'Channel::Instagram': {
+    marks: ['strong', 'em', 'code', 'strike'],
+    nodes: ['bulletList', 'orderedList'],
+    menu: [
+      'strong',
+      'em',
+      'code',
+      'bulletList',
+      'orderedList',
+      'strike',
+      'undo',
+      'redo',
+    ],
+  },
+  'Channel::Voice': {
+    marks: [],
+    nodes: [],
+    menu: [],
+  },
+  // Special contexts (not actual channels)
+  'Context::Default': {
+    marks: ['strong', 'em', 'code', 'link', 'strike'],
+    nodes: ['bulletList', 'orderedList', 'codeBlock', 'blockquote'],
+    menu: [
+      'strong',
+      'em',
+      'code',
+      'link',
+      'strike',
+      'bulletList',
+      'orderedList',
+      'undo',
+      'redo',
+    ],
+  },
+  'Context::MessageSignature': {
+    marks: ['strong', 'em', 'link'],
+    nodes: [],
+    menu: ['strong', 'em', 'link', 'undo', 'redo', 'imageUpload'],
+  },
+  'Context::InboxSettings': {
+    marks: ['strong', 'em', 'link'],
+    nodes: [],
+    menu: ['strong', 'em', 'link', 'undo', 'redo'],
+  },
+};
 
+// Editor menu options for Full Editor
 export const ARTICLE_EDITOR_MENU_OPTIONS = [
   'strong',
   'em',
@@ -33,14 +153,81 @@ export const ARTICLE_EDITOR_MENU_OPTIONS = [
   'code',
 ];
 
-export const WIDGET_BUILDER_EDITOR_MENU_OPTIONS = [
-  'strong',
-  'em',
-  'link',
-  'undo',
-  'redo',
+/**
+ * Markdown formatting patterns for stripping unsupported formatting.
+ *
+ * Maps camelCase type names to ProseMirror snake_case schema names.
+ * Order matters: codeBlock before code to avoid partial matches.
+ */
+export const MARKDOWN_PATTERNS = [
+  // --- BLOCK NODES ---
+  {
+    type: 'codeBlock', // PM: code_block, eg: ```js\ncode\n```
+    patterns: [
+      { pattern: /`{3}(?:\w+)?\n?([\s\S]*?)`{3}/g, replacement: '$1' },
+    ],
+  },
+  {
+    type: 'blockquote', // PM: blockquote, eg: > quote
+    patterns: [{ pattern: /^> ?/gm, replacement: '' }],
+  },
+  {
+    type: 'bulletList', // PM: bullet_list, eg: - item
+    patterns: [{ pattern: /^[\t ]*[-*+]\s+/gm, replacement: '' }],
+  },
+  {
+    type: 'orderedList', // PM: ordered_list, eg: 1. item
+    patterns: [{ pattern: /^[\t ]*\d+\.\s+/gm, replacement: '' }],
+  },
+  {
+    type: 'heading', // PM: heading, eg: ## Heading
+    patterns: [{ pattern: /^#{1,6}\s+/gm, replacement: '' }],
+  },
+  {
+    type: 'horizontalRule', // PM: horizontal_rule, eg: ---
+    patterns: [{ pattern: /^(?:---|___|\*\*\*)\s*$/gm, replacement: '' }],
+  },
+  {
+    type: 'image', // PM: image, eg: ![alt](url)
+    patterns: [{ pattern: /!\[([^\]]*)\]\([^)]+\)/g, replacement: '$1' }],
+  },
+  {
+    type: 'hardBreak', // PM: hard_break, eg: line\\\n or line  \n
+    patterns: [
+      { pattern: /\\\n/g, replacement: '\n' },
+      { pattern: / {2,}\n/g, replacement: '\n' },
+    ],
+  },
+  // --- INLINE MARKS ---
+  {
+    type: 'strong', // PM: strong, eg: **bold** or __bold__
+    patterns: [
+      { pattern: /\*\*(.+?)\*\*/g, replacement: '$1' },
+      { pattern: /__(.+?)__/g, replacement: '$1' },
+    ],
+  },
+  {
+    type: 'em', // PM: em, eg: *italic* or _italic_
+    patterns: [
+      { pattern: /(?<!\*)\*(?!\*)(.+?)(?<!\*)\*(?!\*)/g, replacement: '$1' },
+      { pattern: /(?<!_)_(?!_)(.+?)(?<!_)_(?!_)/g, replacement: '$1' },
+    ],
+  },
+  {
+    type: 'strike', // PM: strike, eg: ~~strikethrough~~
+    patterns: [{ pattern: /~~(.+?)~~/g, replacement: '$1' }],
+  },
+  {
+    type: 'code', // PM: code, eg: `inline code`
+    patterns: [{ pattern: /`([^`]+)`/g, replacement: '$1' }],
+  },
+  {
+    type: 'link', // PM: link, eg: [text](url)
+    patterns: [{ pattern: /\[([^\]]+)\]\([^)]+\)/g, replacement: '$1' }],
+  },
 ];
 
+// Editor image resize options for Message Editor
 export const MESSAGE_EDITOR_IMAGE_RESIZES = [
   {
     name: 'Small',

app/javascript/dashboard/helper/editorHelper.js

@@ -5,6 +5,8 @@ import {
 } from '@chatwoot/prosemirror-schema';
 import { replaceVariablesInMessage } from '@chatwoot/utils';
 import * as Sentry from '@sentry/vue';
+import { FORMATTING, MARKDOWN_PATTERNS } from 'dashboard/constants/editor';
+import camelcaseKeys from 'camelcase-keys';
 
 /**
  * The delimiter used to separate the signature from the rest of the body.
@@ -283,6 +285,47 @@ export function setURLWithQueryAndSize(selectedImageNode, size, editorView) {
   }
 }
 
+/**
+ * Strips unsupported markdown formatting from content based on the editor schema.
+ * This ensures canned responses with rich formatting can be inserted into channels
+ * that don't support certain formatting (e.g., API channels don't support bold).
+ *
+ * @param {string} content - The markdown content to sanitize
+ * @param {Object} schema - The ProseMirror schema with supported marks and nodes
+ * @returns {string} - Content with unsupported formatting stripped
+ */
+export function stripUnsupportedFormatting(content, schema) {
+  if (!content || typeof content !== 'string') return content;
+  if (!schema) return content;
+
+  let sanitizedContent = content;
+
+  // Get supported marks and nodes from the schema
+  // Note: ProseMirror uses snake_case internally (code_block, bullet_list, etc.)
+  // but our FORMATTING constant uses camelCase (codeBlock, bulletList, etc.)
+  // We use camelcase-keys to normalize node names for comparison
+  const supportedMarks = Object.keys(schema.marks || {});
+  const nodeKeys = Object.keys(schema.nodes || {});
+  const nodeKeysObj = Object.fromEntries(nodeKeys.map(k => [k, true]));
+  const supportedNodes = Object.keys(camelcaseKeys(nodeKeysObj));
+
+  // Process each formatting type in order (codeBlock before code is important!)
+  MARKDOWN_PATTERNS.forEach(({ type, patterns }) => {
+    // Check if this format type is supported by the schema
+    const isMarkSupported = supportedMarks.includes(type);
+    const isNodeSupported = supportedNodes.includes(type);
+
+    // If not supported, strip the formatting
+    if (!isMarkSupported && !isNodeSupported) {
+      patterns.forEach(({ pattern, replacement }) => {
+        sanitizedContent = sanitizedContent.replace(pattern, replacement);
+      });
+    }
+  });
+
+  return sanitizedContent;
+}
+
 /**
  * Content Node Creation Helper Functions for
  * - mention
@@ -313,8 +356,17 @@ const createNode = (editorView, nodeType, content) => {
 
       return mentionNode;
     }
-    case 'cannedResponse':
-      return new MessageMarkdownTransformer(messageSchema).parse(content);
+    case 'cannedResponse': {
+      // Strip unsupported formatting before parsing to ensure content can be inserted
+      // into channels that don't support certain markdown features (e.g., API channels)
+      const sanitizedContent = stripUnsupportedFormatting(
+        content,
+        state.schema
+      );
+      return new MessageMarkdownTransformer(state.schema).parse(
+        sanitizedContent
+      );
+    }
     case 'variable':
       return state.schema.text(`{{${content}}}`);
     case 'emoji':
@@ -389,3 +441,85 @@ export const getContentNode = (
     ? creator(editorView, content, from, to, variables)
     : { node: null, from, to };
 };
+
+/**
+ * Get the formatting configuration for a specific channel type.
+ * Returns the appropriate marks, nodes, and menu items for the editor.
+ *
+ * @param {string} channelType - The channel type (e.g., 'Channel::FacebookPage', 'Channel::WebWidget')
+ * @returns {Object} The formatting configuration with marks, nodes, and menu properties
+ */
+export function getFormattingForEditor(channelType) {
+  return FORMATTING[channelType] || FORMATTING['Context::Default'];
+}
+
+/**
+ * Menu Positioning Helpers
+ * Handles floating menu bar positioning for text selection in the editor.
+ */
+
+const MENU_CONFIG = { H: 46, W: 300, GAP: 10 };
+
+/**
+ * Calculate selection coordinates with bias to handle line-wraps correctly.
+ * @param {EditorView} editorView - ProseMirror editor view
+ * @param {Selection} selection - Current text selection
+ * @param {DOMRect} rect - Container bounding rect
+ * @returns {{start: Object, end: Object, selTop: number, onTop: boolean}}
+ */
+export function getSelectionCoords(editorView, selection, rect) {
+  const start = editorView.coordsAtPos(selection.from, 1);
+  const end = editorView.coordsAtPos(selection.to, -1);
+
+  const selTop = Math.min(start.top, end.top);
+  const spaceAbove = selTop - rect.top;
+  const onTop =
+    spaceAbove > MENU_CONFIG.H + MENU_CONFIG.GAP || end.bottom > rect.bottom;
+
+  return { start, end, selTop, onTop };
+}
+
+/**
+ * Calculate anchor position based on selection visibility and RTL direction.
+ * @param {Object} coords - Selection coordinates from getSelectionCoords
+ * @param {DOMRect} rect - Container bounding rect
+ * @param {boolean} isRtl - Whether text direction is RTL
+ * @returns {number} Anchor x-position for menu
+ */
+export function getMenuAnchor(coords, rect, isRtl) {
+  const { start, end, onTop } = coords;
+
+  if (!onTop) return end.left;
+
+  // If start of selection is visible, align to text. Else stick to container edge.
+  if (start.top >= rect.top) return isRtl ? start.right : start.left;
+
+  return isRtl ? rect.right - MENU_CONFIG.GAP : rect.left + MENU_CONFIG.GAP;
+}
+
+/**
+ * Calculate final menu position (left, top) within container bounds.
+ * @param {Object} coords - Selection coordinates from getSelectionCoords
+ * @param {DOMRect} rect - Container bounding rect
+ * @param {boolean} isRtl - Whether text direction is RTL
+ * @returns {{left: number, top: number, width: number}}
+ */
+export function calculateMenuPosition(coords, rect, isRtl) {
+  const { start, end, selTop, onTop } = coords;
+
+  const anchor = getMenuAnchor(coords, rect, isRtl);
+
+  // Calculate Left: shift by width if RTL, then make relative to container
+  const rawLeft = (isRtl ? anchor - MENU_CONFIG.W : anchor) - rect.left;
+
+  // Ensure menu stays within container bounds
+  const left = Math.min(Math.max(0, rawLeft), rect.width - MENU_CONFIG.W);
+
+  // Calculate Top: align to selection or bottom of selection
+  const top = onTop
+    ? Math.max(-26, selTop - rect.top - MENU_CONFIG.H - MENU_CONFIG.GAP)
+    : Math.max(start.bottom, end.bottom) - rect.top + MENU_CONFIG.GAP;
+  return { left, top, width: MENU_CONFIG.W };
+}
+
+/* End Menu Positioning Helpers */

app/javascript/dashboard/helper/specs/editorContentHelper.spec.js

@@ -1,15 +1,11 @@
 // Moved from editorHelper.spec.js to editorContentHelper.spec.js
 // the mock of chatwoot/prosemirror-schema is getting conflicted with other specs
 import { getContentNode } from '../editorHelper';
-import {
-  MessageMarkdownTransformer,
-  messageSchema,
-} from '@chatwoot/prosemirror-schema';
+import { MessageMarkdownTransformer } from '@chatwoot/prosemirror-schema';
 import { replaceVariablesInMessage } from '@chatwoot/utils';
 
 vi.mock('@chatwoot/prosemirror-schema', () => ({
   MessageMarkdownTransformer: vi.fn(),
-  messageSchema: {},
 }));
 
 vi.mock('@chatwoot/utils', () => ({
@@ -62,12 +58,18 @@ describe('getContentNode', () => {
       const to = 10;
       const updatedMessage = 'Hello John';
 
-      replaceVariablesInMessage.mockReturnValue(updatedMessage);
-      MessageMarkdownTransformer.mockImplementation(() => ({
-        parse: vi.fn().mockReturnValue({ textContent: updatedMessage }),
-      }));
+      // Mock the node that will be returned by parse
+      const mockNode = { textContent: updatedMessage };
 
-      const { node } = getContentNode(
+      replaceVariablesInMessage.mockReturnValue(updatedMessage);
+
+      // Mock MessageMarkdownTransformer instance with parse method
+      const mockTransformer = {
+        parse: vi.fn().mockReturnValue(mockNode),
+      };
+      MessageMarkdownTransformer.mockImplementation(() => mockTransformer);
+
+      const result = getContentNode(
         editorView,
         'cannedResponse',
         content,
@@ -79,8 +81,15 @@ describe('getContentNode', () => {
         message: content,
         variables,
       });
-      expect(MessageMarkdownTransformer).toHaveBeenCalledWith(messageSchema);
-      expect(node.textContent).toBe(updatedMessage);
+      expect(MessageMarkdownTransformer).toHaveBeenCalledWith(
+        editorView.state.schema
+      );
+      expect(mockTransformer.parse).toHaveBeenCalledWith(updatedMessage);
+      expect(result.node).toBe(mockNode);
+      expect(result.node.textContent).toBe(updatedMessage);
+      // When textContent matches updatedMessage, from should remain unchanged
+      expect(result.from).toBe(from);
+      expect(result.to).toBe(to);
     });
   });
 

app/javascript/dashboard/helper/specs/editorHelper.spec.js

@@ -9,7 +9,13 @@ import {
   findNodeToInsertImage,
   setURLWithQueryAndSize,
   getContentNode,
+  getFormattingForEditor,
+  getSelectionCoords,
+  getMenuAnchor,
+  calculateMenuPosition,
+  stripUnsupportedFormatting,
 } from '../editorHelper';
+import { FORMATTING } from 'dashboard/constants/editor';
 import { EditorState } from '@chatwoot/prosemirror-schema';
 import { EditorView } from '@chatwoot/prosemirror-schema';
 import { Schema } from 'prosemirror-model';
@@ -258,15 +264,11 @@ describe('insertAtCursor', () => {
     expect(result).toBeUndefined();
   });
 
-  it('should unwrap doc nodes that are wrapped in a paragraph', () => {
-    const docNode = schema.node('doc', null, [
-      schema.node('paragraph', null, [schema.text('Hello')]),
-    ]);
-
+  it('should insert text node at cursor position', () => {
     const editorState = createEditorState();
     const editorView = new EditorView(document.body, { state: editorState });
 
-    insertAtCursor(editorView, docNode, 0);
+    insertAtCursor(editorView, schema.text('Hello'), 0);
 
     // Check if node was unwrapped and inserted correctly
     expect(editorView.state.doc.firstChild.firstChild.text).toBe('Hello');
@@ -626,3 +628,329 @@ describe('getContentNode', () => {
     });
   });
 });
+
+describe('getFormattingForEditor', () => {
+  describe('channel-specific formatting', () => {
+    it('returns full formatting for Email channel', () => {
+      const result = getFormattingForEditor('Channel::Email');
+
+      expect(result).toEqual(FORMATTING['Channel::Email']);
+    });
+
+    it('returns full formatting for WebWidget channel', () => {
+      const result = getFormattingForEditor('Channel::WebWidget');
+
+      expect(result).toEqual(FORMATTING['Channel::WebWidget']);
+    });
+
+    it('returns limited formatting for WhatsApp channel', () => {
+      const result = getFormattingForEditor('Channel::Whatsapp');
+
+      expect(result).toEqual(FORMATTING['Channel::Whatsapp']);
+    });
+
+    it('returns no formatting for API channel', () => {
+      const result = getFormattingForEditor('Channel::Api');
+
+      expect(result).toEqual(FORMATTING['Channel::Api']);
+    });
+
+    it('returns limited formatting for FacebookPage channel', () => {
+      const result = getFormattingForEditor('Channel::FacebookPage');
+
+      expect(result).toEqual(FORMATTING['Channel::FacebookPage']);
+    });
+
+    it('returns no formatting for TwitterProfile channel', () => {
+      const result = getFormattingForEditor('Channel::TwitterProfile');
+
+      expect(result).toEqual(FORMATTING['Channel::TwitterProfile']);
+    });
+
+    it('returns no formatting for SMS channel', () => {
+      const result = getFormattingForEditor('Channel::Sms');
+
+      expect(result).toEqual(FORMATTING['Channel::Sms']);
+    });
+
+    it('returns limited formatting for Telegram channel', () => {
+      const result = getFormattingForEditor('Channel::Telegram');
+
+      expect(result).toEqual(FORMATTING['Channel::Telegram']);
+    });
+
+    it('returns formatting for Instagram channel', () => {
+      const result = getFormattingForEditor('Channel::Instagram');
+
+      expect(result).toEqual(FORMATTING['Channel::Instagram']);
+    });
+  });
+
+  describe('context-specific formatting', () => {
+    it('returns default formatting for Context::Default', () => {
+      const result = getFormattingForEditor('Context::Default');
+
+      expect(result).toEqual(FORMATTING['Context::Default']);
+    });
+
+    it('returns signature formatting for Context::MessageSignature', () => {
+      const result = getFormattingForEditor('Context::MessageSignature');
+
+      expect(result).toEqual(FORMATTING['Context::MessageSignature']);
+    });
+
+    it('returns widget builder formatting for Context::InboxSettings', () => {
+      const result = getFormattingForEditor('Context::InboxSettings');
+
+      expect(result).toEqual(FORMATTING['Context::InboxSettings']);
+    });
+  });
+
+  describe('fallback behavior', () => {
+    it('returns default formatting for unknown channel type', () => {
+      const result = getFormattingForEditor('Channel::Unknown');
+
+      expect(result).toEqual(FORMATTING['Context::Default']);
+    });
+
+    it('returns default formatting for null channel type', () => {
+      const result = getFormattingForEditor(null);
+
+      expect(result).toEqual(FORMATTING['Context::Default']);
+    });
+
+    it('returns default formatting for undefined channel type', () => {
+      const result = getFormattingForEditor(undefined);
+
+      expect(result).toEqual(FORMATTING['Context::Default']);
+    });
+
+    it('returns default formatting for empty string', () => {
+      const result = getFormattingForEditor('');
+
+      expect(result).toEqual(FORMATTING['Context::Default']);
+    });
+  });
+
+  describe('return value structure', () => {
+    it('always returns an object with marks, nodes, and menu properties', () => {
+      const result = getFormattingForEditor('Channel::Email');
+
+      expect(result).toHaveProperty('marks');
+      expect(result).toHaveProperty('nodes');
+      expect(result).toHaveProperty('menu');
+      expect(Array.isArray(result.marks)).toBe(true);
+      expect(Array.isArray(result.nodes)).toBe(true);
+      expect(Array.isArray(result.menu)).toBe(true);
+    });
+  });
+});
+
+describe('stripUnsupportedFormatting', () => {
+  describe('when schema supports all formatting', () => {
+    const fullSchema = {
+      marks: { strong: {}, em: {}, code: {}, strike: {}, link: {} },
+      nodes: { bulletList: {}, orderedList: {}, codeBlock: {}, blockquote: {} },
+    };
+
+    it('preserves all formatting when schema supports it', () => {
+      const content = '**bold** and *italic* and `code`';
+      expect(stripUnsupportedFormatting(content, fullSchema)).toBe(content);
+    });
+
+    it('preserves links when schema supports them', () => {
+      const content = 'Check [this link](https://example.com)';
+      expect(stripUnsupportedFormatting(content, fullSchema)).toBe(content);
+    });
+
+    it('preserves lists when schema supports them', () => {
+      const content = '- item 1\n- item 2\n1. first\n2. second';
+      expect(stripUnsupportedFormatting(content, fullSchema)).toBe(content);
+    });
+  });
+
+  describe('when schema has no formatting support (eg:SMS channel)', () => {
+    const emptySchema = {
+      marks: {},
+      nodes: {},
+    };
+
+    it('strips bold formatting', () => {
+      expect(stripUnsupportedFormatting('**bold text**', emptySchema)).toBe(
+        'bold text'
+      );
+      expect(stripUnsupportedFormatting('__bold text__', emptySchema)).toBe(
+        'bold text'
+      );
+    });
+
+    it('strips italic formatting', () => {
+      expect(stripUnsupportedFormatting('*italic text*', emptySchema)).toBe(
+        'italic text'
+      );
+      expect(stripUnsupportedFormatting('_italic text_', emptySchema)).toBe(
+        'italic text'
+      );
+    });
+
+    it('strips inline code formatting', () => {
+      expect(stripUnsupportedFormatting('`inline code`', emptySchema)).toBe(
+        'inline code'
+      );
+    });
+
+    it('strips strikethrough formatting', () => {
+      expect(stripUnsupportedFormatting('~~strikethrough~~', emptySchema)).toBe(
+        'strikethrough'
+      );
+    });
+
+    it('strips links but keeps text', () => {
+      expect(
+        stripUnsupportedFormatting(
+          'Check [this link](https://example.com)',
+          emptySchema
+        )
+      ).toBe('Check this link');
+    });
+
+    it('strips bullet list markers', () => {
+      expect(
+        stripUnsupportedFormatting('- item 1\n- item 2', emptySchema)
+      ).toBe('item 1\nitem 2');
+      expect(
+        stripUnsupportedFormatting('* item 1\n* item 2', emptySchema)
+      ).toBe('item 1\nitem 2');
+    });
+
+    it('strips ordered list markers', () => {
+      expect(
+        stripUnsupportedFormatting('1. first\n2. second', emptySchema)
+      ).toBe('first\nsecond');
+    });
+
+    it('strips code block markers', () => {
+      expect(
+        stripUnsupportedFormatting('```javascript\ncode here\n```', emptySchema)
+      ).toBe('code here\n');
+    });
+
+    it('strips blockquote markers', () => {
+      expect(stripUnsupportedFormatting('> quoted text', emptySchema)).toBe(
+        'quoted text'
+      );
+    });
+
+    it('handles complex content with multiple formatting types', () => {
+      const content =
+        '**Bold** and *italic* with `code` and [link](url)\n- list item';
+      const expected = 'Bold and italic with code and link\nlist item';
+      expect(stripUnsupportedFormatting(content, emptySchema)).toBe(expected);
+    });
+  });
+
+  describe('when schema has partial support', () => {
+    const partialSchema = {
+      marks: { strong: {}, em: {} },
+      nodes: {},
+    };
+
+    it('preserves supported marks and strips unsupported ones', () => {
+      const content = '**bold** and `code`';
+      expect(stripUnsupportedFormatting(content, partialSchema)).toBe(
+        '**bold** and code'
+      );
+    });
+
+    it('strips unsupported nodes but keeps supported marks', () => {
+      const content = '**bold** text\n- list item';
+      expect(stripUnsupportedFormatting(content, partialSchema)).toBe(
+        '**bold** text\nlist item'
+      );
+    });
+  });
+
+  describe('edge cases', () => {
+    it('returns content unchanged if content is empty', () => {
+      expect(stripUnsupportedFormatting('', {})).toBe('');
+    });
+
+    it('returns content unchanged if content is null', () => {
+      expect(stripUnsupportedFormatting(null, {})).toBe(null);
+    });
+
+    it('returns content unchanged if content is undefined', () => {
+      expect(stripUnsupportedFormatting(undefined, {})).toBe(undefined);
+    });
+
+    it('returns content unchanged if schema is null', () => {
+      expect(stripUnsupportedFormatting('**bold**', null)).toBe('**bold**');
+    });
+
+    it('handles nested formatting correctly', () => {
+      const emptySchema = { marks: {}, nodes: {} };
+      // After stripping bold (**), the remaining *and italic* becomes italic and is stripped too
+      expect(
+        stripUnsupportedFormatting('**bold *and italic***', emptySchema)
+      ).toBe('bold and italic');
+    });
+  });
+});
+
+describe('Menu positioning helpers', () => {
+  const mockEditorView = {
+    coordsAtPos: vi.fn((pos, bias) => {
+      // Return different coords based on position
+      if (bias === 1) return { top: 100, bottom: 120, left: 50, right: 100 };
+      return { top: 100, bottom: 120, left: 150, right: 200 };
+    }),
+  };
+
+  const wrapperRect = { top: 50, bottom: 300, left: 0, right: 400, width: 400 };
+
+  describe('getSelectionCoords', () => {
+    it('returns selection coordinates with onTop flag', () => {
+      const selection = { from: 0, to: 10 };
+      const result = getSelectionCoords(mockEditorView, selection, wrapperRect);
+
+      expect(result).toHaveProperty('start');
+      expect(result).toHaveProperty('end');
+      expect(result).toHaveProperty('selTop');
+      expect(result).toHaveProperty('onTop');
+    });
+  });
+
+  describe('getMenuAnchor', () => {
+    it('returns end.left when menu is below selection', () => {
+      const coords = { start: { left: 50 }, end: { left: 150 }, onTop: false };
+      expect(getMenuAnchor(coords, wrapperRect, false)).toBe(150);
+    });
+
+    it('returns start.left for LTR when menu is above and visible', () => {
+      const coords = { start: { top: 100, left: 50 }, end: {}, onTop: true };
+      expect(getMenuAnchor(coords, wrapperRect, false)).toBe(50);
+    });
+
+    it('returns start.right for RTL when menu is above and visible', () => {
+      const coords = { start: { top: 100, right: 100 }, end: {}, onTop: true };
+      expect(getMenuAnchor(coords, wrapperRect, true)).toBe(100);
+    });
+  });
+
+  describe('calculateMenuPosition', () => {
+    it('returns bounded left and top positions', () => {
+      const coords = {
+        start: { top: 100, bottom: 120, left: 50 },
+        end: { top: 100, bottom: 120, left: 150 },
+        selTop: 100,
+        onTop: false,
+      };
+      const result = calculateMenuPosition(coords, wrapperRect, false);
+
+      expect(result).toHaveProperty('left');
+      expect(result).toHaveProperty('top');
+      expect(result).toHaveProperty('width', 300);
+      expect(result.left).toBeGreaterThanOrEqual(0);
+    });
+  });
+});

app/javascript/dashboard/i18n/locale/en/conversation.json

@@ -196,7 +196,6 @@
       "INSERT_READ_MORE": "Read more",
       "DISMISS_REPLY": "Dismiss reply",
       "REPLYING_TO": "Replying to:",
-      "TIP_FORMAT_ICON": "Show rich text editor",
       "TIP_EMOJI_ICON": "Show emoji selector",
       "TIP_ATTACH_ICON": "Attach files",
       "TIP_AUDIORECORDER_ICON": "Record audio",

app/javascript/dashboard/i18n/locale/en/settings.json

@@ -399,15 +399,39 @@
       "DESCRIPTION": "Manage usage and credits for Captain AI.",
       "BUTTON_TXT": "Buy more credits",
       "DOCUMENTS": "Documents",
-      "RESPONSES": "Responses",
-      "UPGRADE": "Captain is not available on the free plan, upgrade now to get access to assistants, copilot and more."
+      "RESPONSES": "Credits",
+      "UPGRADE": "Captain is not available on the free plan, upgrade now to get access to assistants, copilot and more.",
+      "REFRESH_CREDITS": "Refresh"
     },
     "CHAT_WITH_US": {
       "TITLE": "Need help?",
       "DESCRIPTION": "Do you face any issues in billing? We are here to help.",
       "BUTTON_TXT": "Chat with us"
     },
-    "NO_BILLING_USER": "Your billing account is being configured. Please refresh the page and try again."
+    "NO_BILLING_USER": "Your billing account is being configured. Please refresh the page and try again.",
+    "TOPUP": {
+      "BUY_CREDITS": "Buy more credits",
+      "MODAL_TITLE": "Buy AI Credits",
+      "MODAL_DESCRIPTION": "Purchase additional credits for Captain AI.",
+      "CREDITS": "CREDITS",
+      "ONE_TIME": "one-time",
+      "POPULAR": "Most Popular",
+      "NOTE_TITLE": "Note:",
+      "NOTE_DESCRIPTION": "Credits are added immediately and expire in 6 months. An active subscription is required to use credits. Purchased credits are consumed after your monthly plan credits.",
+      "CANCEL": "Cancel",
+      "PURCHASE": "Purchase Credits",
+      "LOADING": "Loading options...",
+      "FETCH_ERROR": "Failed to load credit options. Please try again.",
+      "PURCHASE_ERROR": "Failed to process purchase. Please try again.",
+      "PURCHASE_SUCCESS": "Successfully added {credits} credits to your account",
+      "CONFIRM": {
+        "TITLE": "Confirm Purchase",
+        "DESCRIPTION": "You are about to purchase {credits} credits for {amount}.",
+        "INSTANT_DEDUCTION_NOTE": "Your saved card will be charged immediately upon confirmation.",
+        "GO_BACK": "Go Back",
+        "CONFIRM_PURCHASE": "Confirm Purchase"
+      }
+    }
   },
   "SECURITY_SETTINGS": {
     "TITLE": "Security",

app/javascript/dashboard/routes/dashboard/conversation/ContactPanel.vue

@@ -5,7 +5,9 @@ import {
   useFunctionGetter,
   useStore,
 } from 'dashboard/composables/store';
+import { useAccount } from 'dashboard/composables/useAccount';
 import { useUISettings } from 'dashboard/composables/useUISettings';
+import { FEATURE_FLAGS } from 'dashboard/featureFlags';
 
 import AccordionItem from 'dashboard/components/Accordion/AccordionItem.vue';
 import ContactConversations from './ContactConversations.vue';
@@ -52,12 +54,22 @@ const isShopifyFeatureEnabled = computed(
   () => shopifyIntegration.value.enabled
 );
 
+const { isCloudFeatureEnabled } = useAccount();
+
+const isLinearFeatureEnabled = computed(() =>
+  isCloudFeatureEnabled(FEATURE_FLAGS.LINEAR)
+);
+
 const linearIntegration = useFunctionGetter(
   'integrations/getIntegration',
   'linear'
 );
 
-const isLinearIntegrationEnabled = computed(
+const isLinearClientIdConfigured = computed(() => {
+  return !!linearIntegration.value?.id;
+});
+
+const isLinearConnected = computed(
   () => linearIntegration.value?.enabled || false
 );
 
@@ -238,7 +250,13 @@ onMounted(() => {
               <MacrosList :conversation-id="conversationId" />
             </AccordionItem>
           </woot-feature-toggle>
-          <div v-else-if="element.name === 'linear_issues'">
+          <div
+            v-else-if="
+              element.name === 'linear_issues' &&
+              isLinearFeatureEnabled &&
+              isLinearClientIdConfigured
+            "
+          >
             <AccordionItem
               :title="$t('CONVERSATION_SIDEBAR.ACCORDION.LINEAR_ISSUES')"
               :is-open="isContactSidebarItemOpen('is_linear_issues_open')"
@@ -247,7 +265,7 @@ onMounted(() => {
                 value => toggleSidebarUIState('is_linear_issues_open', value)
               "
             >
-              <LinearSetupCTA v-if="!isLinearIntegrationEnabled" />
+              <LinearSetupCTA v-if="!isLinearConnected" />
               <LinearIssuesList v-else :conversation-id="conversationId" />
             </AccordionItem>
           </div>

app/javascript/dashboard/routes/dashboard/settings/billing/Index.vue

@@ -11,6 +11,7 @@ import BillingMeter from './components/BillingMeter.vue';
 import BillingCard from './components/BillingCard.vue';
 import BillingHeader from './components/BillingHeader.vue';
 import DetailItem from './components/DetailItem.vue';
+import PurchaseCreditsModal from './components/PurchaseCreditsModal.vue';
 import BaseSettingsHeader from '../components/BaseSettingsHeader.vue';
 import SettingsLayout from '../SettingsLayout.vue';
 import ButtonV4 from 'next/button/Button.vue';
@@ -23,6 +24,7 @@ const {
   documentLimits,
   responseLimits,
   fetchLimits,
+  isFetchingLimits,
 } = useCaptain();
 
 const uiFlags = useMapGetter('accounts/getUIFlags');
@@ -32,6 +34,7 @@ const BILLING_REFRESH_ATTEMPTED = 'billing_refresh_attempted';
 
 // State for handling refresh attempts and loading
 const isWaitingForBilling = ref(false);
+const purchaseCreditsModalRef = ref(null);
 
 const customAttributes = computed(() => {
   return currentAccount.value.custom_attributes || {};
@@ -45,6 +48,11 @@ const planName = computed(() => {
   return customAttributes.value.plan_name;
 });
 
+const canPurchaseCredits = computed(() => {
+  const plan = planName.value?.toLowerCase();
+  return plan && plan !== 'hacker';
+});
+
 /**
  * Computed property for subscribed quantity
  * @returns {number|undefined}
@@ -71,8 +79,9 @@ const hasABillingPlan = computed(() => {
 const fetchAccountDetails = async () => {
   if (!hasABillingPlan.value) {
     await store.dispatch('accounts/subscription');
-    fetchLimits();
   }
+  // Always fetch limits for billing page to show credit usage
+  fetchLimits();
 };
 
 const handleBillingPageLogic = async () => {
@@ -119,6 +128,15 @@ const onToggleChatWindow = () => {
   }
 };
 
+const openPurchaseCreditsModal = () => {
+  purchaseCreditsModalRef.value?.open();
+};
+
+const handleTopupSuccess = () => {
+  // Refresh limits to show updated credit balance
+  fetchLimits();
+};
+
 onMounted(handleBillingPageLogic);
 </script>
 
@@ -178,9 +196,27 @@ onMounted(handleBillingPageLogic);
           :description="$t('BILLING_SETTINGS.CAPTAIN.DESCRIPTION')"
         >
           <template #action>
-            <ButtonV4 sm faded slate disabled>
-              {{ $t('BILLING_SETTINGS.CAPTAIN.BUTTON_TXT') }}
-            </ButtonV4>
+            <div class="flex gap-2">
+              <ButtonV4
+                sm
+                flushed
+                slate
+                icon="i-lucide-refresh-cw"
+                :is-loading="isFetchingLimits"
+                @click="fetchLimits"
+              >
+                {{ $t('BILLING_SETTINGS.CAPTAIN.REFRESH_CREDITS') }}
+              </ButtonV4>
+              <ButtonV4
+                v-if="canPurchaseCredits"
+                sm
+                solid
+                blue
+                @click="openPurchaseCreditsModal"
+              >
+                {{ $t('BILLING_SETTINGS.TOPUP.BUY_CREDITS') }}
+              </ButtonV4>
+            </div>
           </template>
           <div v-if="captainLimits && responseLimits" class="px-5">
             <BillingMeter
@@ -223,6 +259,10 @@ onMounted(handleBillingPageLogic);
           </ButtonV4>
         </BillingHeader>
       </section>
+      <PurchaseCreditsModal
+        ref="purchaseCreditsModalRef"
+        @success="handleTopupSuccess"
+      />
     </template>
   </SettingsLayout>
 </template>

app/javascript/dashboard/routes/dashboard/settings/billing/components/CreditPackageCard.vue

@@ -0,0 +1,101 @@
+<script setup>
+defineProps({
+  credits: {
+    type: Number,
+    required: true,
+  },
+  amount: {
+    type: Number,
+    required: true,
+  },
+  currency: {
+    type: String,
+    default: 'usd',
+  },
+  isSelected: {
+    type: Boolean,
+    default: false,
+  },
+  isPopular: {
+    type: Boolean,
+    default: false,
+  },
+  name: {
+    type: String,
+    required: true,
+  },
+});
+
+const emit = defineEmits(['select']);
+
+const formatCredits = credits => {
+  return credits.toLocaleString();
+};
+
+const formatAmount = (amount, currency) => {
+  return new Intl.NumberFormat('en-US', {
+    style: 'currency',
+    currency: currency.toUpperCase(),
+    minimumFractionDigits: 0,
+  }).format(amount);
+};
+</script>
+
+<template>
+  <label
+    class="relative flex flex-col p-6 border-2 rounded-xl transition-all cursor-pointer bg-n-solid-1 hover:bg-n-solid-2"
+    :class="[
+      isSelected ? 'border-woot-500' : 'border-n-weak hover:border-n-strong',
+    ]"
+  >
+    <input
+      type="radio"
+      :name="name"
+      :value="credits"
+      :checked="isSelected"
+      class="sr-only"
+      @change="emit('select')"
+    />
+    <span
+      v-if="isPopular"
+      class="absolute -top-3 left-4 px-3 py-1 text-xs font-medium rounded"
+      :class="
+        isSelected ? 'bg-woot-500 text-white' : 'bg-n-solid-3 text-n-slate-11'
+      "
+    >
+      {{ $t('BILLING_SETTINGS.TOPUP.POPULAR') }}
+    </span>
+    <div
+      v-if="isSelected"
+      class="absolute top-4 right-4 flex items-center justify-center w-6 h-6 rounded-full bg-woot-500"
+    >
+      <svg
+        class="w-4 h-4 text-white"
+        fill="none"
+        stroke="currentColor"
+        viewBox="0 0 24 24"
+      >
+        <path
+          stroke-linecap="round"
+          stroke-linejoin="round"
+          stroke-width="2"
+          d="M5 13l4 4L19 7"
+        />
+      </svg>
+    </div>
+    <span class="text-3xl font-normal text-n-slate-12 mb-2 tracking-tighter">
+      {{ formatCredits(credits) }}
+    </span>
+    <span
+      class="text-xs font-normal text-n-slate-11 uppercase tracking-tight mb-6"
+    >
+      {{ $t('BILLING_SETTINGS.TOPUP.CREDITS') }}
+    </span>
+    <span class="text-2xl font-normal text-n-slate-12 tracking-tight">
+      {{ formatAmount(amount, currency) }}
+      <span class="text-sm text-n-slate-11 ml-0.5">{{
+        $t('BILLING_SETTINGS.TOPUP.ONE_TIME')
+      }}</span>
+    </span>
+  </label>
+</template>

app/javascript/dashboard/routes/dashboard/settings/billing/components/PurchaseCreditsModal.vue

@@ -0,0 +1,220 @@
+<script setup>
+import { ref, computed } from 'vue';
+import { useI18n } from 'vue-i18n';
+import { useAlert } from 'dashboard/composables';
+import Dialog from 'dashboard/components-next/dialog/Dialog.vue';
+import Button from 'dashboard/components-next/button/Button.vue';
+import CreditPackageCard from './CreditPackageCard.vue';
+import EnterpriseAccountAPI from 'dashboard/api/enterprise/account';
+
+const emit = defineEmits(['close', 'success']);
+
+const { t } = useI18n();
+
+const TOPUP_OPTIONS = [
+  { credits: 1000, amount: 20.0, currency: 'usd' },
+  { credits: 2500, amount: 50.0, currency: 'usd' },
+  { credits: 6000, amount: 100.0, currency: 'usd' },
+  { credits: 12000, amount: 200.0, currency: 'usd' },
+];
+
+const POPULAR_CREDITS_AMOUNT = 6000;
+const STEP_SELECT = 'select';
+const STEP_CONFIRM = 'confirm';
+
+const dialogRef = ref(null);
+const selectedCredits = ref(null);
+const isLoading = ref(false);
+const currentStep = ref(STEP_SELECT);
+
+const selectedOption = computed(() => {
+  return TOPUP_OPTIONS.find(o => o.credits === selectedCredits.value);
+});
+
+const formattedAmount = computed(() => {
+  if (!selectedOption.value) return '';
+  return new Intl.NumberFormat('en-US', {
+    style: 'currency',
+    currency: selectedOption.value.currency.toUpperCase(),
+  }).format(selectedOption.value.amount);
+});
+
+const formattedCredits = computed(() => {
+  if (!selectedOption.value) return '';
+  return selectedOption.value.credits.toLocaleString();
+});
+
+const dialogTitle = computed(() => {
+  return currentStep.value === STEP_SELECT
+    ? t('BILLING_SETTINGS.TOPUP.MODAL_TITLE')
+    : t('BILLING_SETTINGS.TOPUP.CONFIRM.TITLE');
+});
+
+const dialogDescription = computed(() => {
+  return currentStep.value === STEP_SELECT
+    ? t('BILLING_SETTINGS.TOPUP.MODAL_DESCRIPTION')
+    : '';
+});
+
+const dialogWidth = computed(() => {
+  return currentStep.value === STEP_SELECT ? 'xl' : 'md';
+});
+
+const handlePackageSelect = credits => {
+  selectedCredits.value = credits;
+};
+
+const open = () => {
+  const popularOption = TOPUP_OPTIONS.find(
+    o => o.credits === POPULAR_CREDITS_AMOUNT
+  );
+  selectedCredits.value = popularOption?.credits || TOPUP_OPTIONS[0]?.credits;
+  currentStep.value = STEP_SELECT;
+  isLoading.value = false;
+  dialogRef.value?.open();
+};
+
+const close = () => {
+  dialogRef.value?.close();
+};
+
+const handleClose = () => {
+  emit('close');
+};
+
+const goToConfirmStep = () => {
+  if (!selectedOption.value) return;
+  currentStep.value = STEP_CONFIRM;
+};
+
+const goBackToSelectStep = () => {
+  currentStep.value = STEP_SELECT;
+};
+
+const handlePurchase = async () => {
+  if (!selectedOption.value) return;
+
+  isLoading.value = true;
+  try {
+    const response = await EnterpriseAccountAPI.createTopupCheckout(
+      selectedOption.value.credits
+    );
+
+    close();
+    emit('success', response.data);
+    useAlert(
+      t('BILLING_SETTINGS.TOPUP.PURCHASE_SUCCESS', {
+        credits: response.data.credits,
+      })
+    );
+  } catch (error) {
+    const errorMessage =
+      error.response?.data?.error || t('BILLING_SETTINGS.TOPUP.PURCHASE_ERROR');
+    useAlert(errorMessage);
+  } finally {
+    isLoading.value = false;
+  }
+};
+
+defineExpose({ open, close });
+</script>
+
+<template>
+  <Dialog
+    ref="dialogRef"
+    :title="dialogTitle"
+    :description="dialogDescription"
+    :width="dialogWidth"
+    :show-confirm-button="false"
+    :show-cancel-button="false"
+    @close="handleClose"
+  >
+    <!-- Step 1: Select Credits Package -->
+    <template v-if="currentStep === 'select'">
+      <div class="grid grid-cols-2 gap-4">
+        <CreditPackageCard
+          v-for="option in TOPUP_OPTIONS"
+          :key="option.credits"
+          name="credit-package"
+          :credits="option.credits"
+          :amount="option.amount"
+          :currency="option.currency"
+          :is-popular="option.credits === POPULAR_CREDITS_AMOUNT"
+          :is-selected="selectedCredits === option.credits"
+          @select="handlePackageSelect(option.credits)"
+        />
+      </div>
+
+      <div class="p-4 mt-6 rounded-lg bg-n-solid-2 border border-n-weak">
+        <p class="text-sm text-n-slate-11">
+          <span class="font-semibold text-n-slate-12">{{
+            $t('BILLING_SETTINGS.TOPUP.NOTE_TITLE')
+          }}</span>
+          {{ $t('BILLING_SETTINGS.TOPUP.NOTE_DESCRIPTION') }}
+        </p>
+      </div>
+    </template>
+
+    <!-- Step 2: Confirm Purchase -->
+    <template v-else>
+      <div class="flex flex-col gap-4">
+        <p class="text-sm text-n-slate-11">
+          {{
+            $t('BILLING_SETTINGS.TOPUP.CONFIRM.DESCRIPTION', {
+              credits: formattedCredits,
+              amount: formattedAmount,
+            })
+          }}
+        </p>
+
+        <div class="p-2.5 rounded-lg bg-n-amber-2 border border-n-amber-6">
+          <p class="text-sm text-n-amber-11">
+            {{ $t('BILLING_SETTINGS.TOPUP.CONFIRM.INSTANT_DEDUCTION_NOTE') }}
+          </p>
+        </div>
+      </div>
+    </template>
+
+    <template #footer>
+      <!-- Step 1 Footer -->
+      <div
+        v-if="currentStep === 'select'"
+        class="flex items-center justify-between w-full gap-3"
+      >
+        <Button
+          variant="faded"
+          color="slate"
+          :label="$t('BILLING_SETTINGS.TOPUP.CANCEL')"
+          class="w-full"
+          @click="close"
+        />
+        <Button
+          color="blue"
+          :label="$t('BILLING_SETTINGS.TOPUP.PURCHASE')"
+          class="w-full"
+          :disabled="!selectedCredits"
+          @click="goToConfirmStep"
+        />
+      </div>
+
+      <!-- Step 2 Footer -->
+      <div v-else class="flex items-center justify-between w-full gap-3">
+        <Button
+          variant="faded"
+          color="slate"
+          :label="$t('BILLING_SETTINGS.TOPUP.CONFIRM.GO_BACK')"
+          class="w-full"
+          :disabled="isLoading"
+          @click="goBackToSelectStep"
+        />
+        <Button
+          color="blue"
+          :label="$t('BILLING_SETTINGS.TOPUP.CONFIRM.CONFIRM_PURCHASE')"
+          class="w-full"
+          :is-loading="isLoading"
+          @click="handlePurchase"
+        />
+      </div>
+    </template>
+  </Dialog>
+</template>

app/javascript/dashboard/routes/dashboard/settings/canned/AddCanned.vue

@@ -110,6 +110,7 @@ export default {
               v-model="content"
               class="message-editor [&>div]:px-1"
               :class="{ editor_warning: v$.content.$error }"
+              channel-type="Context::Default"
               enable-variables
               :enable-canned-responses="false"
               :placeholder="$t('CANNED_MGMT.ADD.FORM.CONTENT.PLACEHOLDER')"

app/javascript/dashboard/routes/dashboard/settings/canned/EditCanned.vue

@@ -114,6 +114,7 @@ export default {
               v-model="content"
               class="message-editor [&>div]:px-1"
               :class="{ editor_warning: v$.content.$error }"
+              channel-type="Context::Default"
               enable-variables
               :enable-canned-responses="false"
               :placeholder="$t('CANNED_MGMT.EDIT.FORM.CONTENT.PLACEHOLDER')"

app/javascript/dashboard/routes/dashboard/settings/inbox/Settings.vue

@@ -27,7 +27,6 @@ import { FEATURE_FLAGS } from '../../../../featureFlags';
 import SenderNameExamplePreview from './components/SenderNameExamplePreview.vue';
 import NextButton from 'dashboard/components-next/button/Button.vue';
 import { INBOX_TYPES } from 'dashboard/helper/inbox';
-import { WIDGET_BUILDER_EDITOR_MENU_OPTIONS } from 'dashboard/constants/editor';
 import { getInboxIconByType } from 'dashboard/helper/inbox';
 import Editor from 'dashboard/components-next/Editor/Editor.vue';
 
@@ -81,7 +80,6 @@ export default {
       selectedTabIndex: 0,
       selectedPortalSlug: '',
       showBusinessNameInput: false,
-      welcomeTaglineEditorMenuOptions: WIDGET_BUILDER_EDITOR_MENU_OPTIONS,
       healthData: null,
       isLoadingHealth: false,
       healthError: null,
@@ -626,7 +624,7 @@ export default {
               )
             "
             :max-length="255"
-            :enabled-menu-options="welcomeTaglineEditorMenuOptions"
+            channel-type="Context::InboxSettings"
           />
 
           <label v-if="isAWebWidgetInbox" class="pb-4">

app/javascript/dashboard/routes/dashboard/settings/inbox/WidgetBuilder.vue

@@ -7,7 +7,6 @@ import { useVuelidate } from '@vuelidate/core';
 import { required } from '@vuelidate/validators';
 import { LOCAL_STORAGE_KEYS } from 'dashboard/constants/localStorage';
 import { LocalStorage } from 'shared/helpers/localStorage';
-import { WIDGET_BUILDER_EDITOR_MENU_OPTIONS } from 'dashboard/constants/editor';
 import NextButton from 'dashboard/components-next/button/Button.vue';
 import Avatar from 'next/avatar/Avatar.vue';
 import Editor from 'dashboard/components-next/Editor/Editor.vue';
@@ -76,7 +75,6 @@ export default {
           checked: false,
         },
       ],
-      welcomeTaglineEditorMenuOptions: WIDGET_BUILDER_EDITOR_MENU_OPTIONS,
     };
   },
   computed: {
@@ -337,7 +335,7 @@ export default {
                 )
               "
               :max-length="255"
-              :enabled-menu-options="welcomeTaglineEditorMenuOptions"
+              channel-type="Context::InboxSettings"
               class="mb-4"
             />
             <label>

app/javascript/dashboard/routes/dashboard/settings/inbox/channels/Website.vue

@@ -5,7 +5,6 @@ import router from '../../../../index';
 import NextButton from 'dashboard/components-next/button/Button.vue';
 import PageHeader from '../../SettingsSubPageHeader.vue';
 import GreetingsEditor from 'shared/components/GreetingsEditor.vue';
-import { WIDGET_BUILDER_EDITOR_MENU_OPTIONS } from 'dashboard/constants/editor';
 import Editor from 'dashboard/components-next/Editor/Editor.vue';
 
 export default {
@@ -24,7 +23,6 @@ export default {
       channelWelcomeTagline: '',
       greetingEnabled: false,
       greetingMessage: '',
-      welcomeTaglineEditorMenuOptions: WIDGET_BUILDER_EDITOR_MENU_OPTIONS,
     };
   },
   computed: {
@@ -147,7 +145,7 @@ export default {
           )
         "
         :max-length="255"
-        :enabled-menu-options="welcomeTaglineEditorMenuOptions"
+        channel-type="Context::InboxSettings"
         class="mb-4"
       />
 

app/javascript/dashboard/routes/dashboard/settings/profile/MessageSignature.vue

@@ -1,7 +1,6 @@
 <script setup>
 import { ref, watch } from 'vue';
 import WootMessageEditor from 'dashboard/components/widgets/WootWriter/Editor.vue';
-import { MESSAGE_SIGNATURE_EDITOR_MENU_OPTIONS } from 'dashboard/constants/editor';
 import NextButton from 'dashboard/components-next/button/Button.vue';
 
 const props = defineProps({
@@ -12,7 +11,6 @@ const props = defineProps({
 });
 
 const emit = defineEmits(['updateSignature']);
-const customEditorMenuList = MESSAGE_SIGNATURE_EDITOR_MENU_OPTIONS;
 const signature = ref(props.messageSignature);
 watch(
   () => props.messageSignature ?? '',
@@ -34,7 +32,7 @@ const updateSignature = () => {
       class="message-editor h-[10rem] !px-3"
       is-format-mode
       :placeholder="$t('PROFILE_SETTINGS.FORM.MESSAGE_SIGNATURE.PLACEHOLDER')"
-      :enabled-menu-options="customEditorMenuList"
+      channel-type="Context::MessageSignature"
       :enable-suggestions="false"
       show-image-resize-toolbar
     />

app/javascript/dashboard/store/modules/accounts.js

@@ -18,6 +18,7 @@ const state = {
     isFetchingItem: false,
     isUpdating: false,
     isCheckoutInProcess: false,
+    isFetchingLimits: false,
   },
 };
 
@@ -141,11 +142,14 @@ export const actions = {
   },
 
   limits: async ({ commit }) => {
+    commit(types.default.SET_ACCOUNT_UI_FLAG, { isFetchingLimits: true });
     try {
       const response = await EnterpriseAccountAPI.getLimits();
       commit(types.default.SET_ACCOUNT_LIMITS, response.data);
     } catch (error) {
       // silent error
+    } finally {
+      commit(types.default.SET_ACCOUNT_UI_FLAG, { isFetchingLimits: false });
     }
   },
 

app/jobs/data_import_job.rb

@@ -30,21 +30,15 @@ class DataImportJob < ApplicationJob
   def parse_csv_and_build_contacts
     contacts = []
     rejected_contacts = []
-    # Ensuring that importing non utf-8 characters will not throw error
-    data = @data_import.import_file.download
-    utf8_data = data.force_encoding('UTF-8')
 
-    # Ensure that the data is valid UTF-8, preserving valid characters
-    clean_data = utf8_data.valid_encoding? ? utf8_data : utf8_data.encode('UTF-16le', invalid: :replace, replace: '').encode('UTF-8')
-
-    csv = CSV.parse(clean_data, headers: true)
-
-    csv.each do |row|
-      current_contact = @contact_manager.build_contact(row.to_h.with_indifferent_access)
-      if current_contact.valid?
-        contacts << current_contact
-      else
-        append_rejected_contact(row, current_contact, rejected_contacts)
+    with_import_file do |file|
+      csv_reader(file).each do |row|
+        current_contact = @contact_manager.build_contact(row.to_h.with_indifferent_access)
+        if current_contact.valid?
+          contacts << current_contact
+        else
+          append_rejected_contact(row, current_contact, rejected_contacts)
+        end
       end
     end
 
@@ -75,7 +69,7 @@ class DataImportJob < ApplicationJob
   end
 
   def generate_csv_data(rejected_contacts)
-    headers = CSV.parse(@data_import.import_file.download, headers: true).headers
+    headers = csv_headers
     headers << 'errors'
     return if rejected_contacts.blank?
 
@@ -99,4 +93,31 @@ class DataImportJob < ApplicationJob
   def send_import_failed_notification_to_admin
     AdministratorNotifications::AccountNotificationMailer.with(account: @data_import.account).contact_import_failed.deliver_later
   end
+
+  def csv_headers
+    header_row = nil
+    with_import_file do |file|
+      header_row = csv_reader(file).first
+    end
+    header_row&.headers || []
+  end
+
+  def csv_reader(file)
+    file.rewind
+    raw_data = file.read
+    utf8_data = raw_data.force_encoding('UTF-8')
+    clean_data = utf8_data.valid_encoding? ? utf8_data : utf8_data.encode('UTF-16le', invalid: :replace, replace: '').encode('UTF-8')
+
+    CSV.new(StringIO.new(clean_data), headers: true)
+  end
+
+  def with_import_file
+    temp_dir = Rails.root.join('tmp/imports')
+    FileUtils.mkdir_p(temp_dir)
+
+    @data_import.import_file.open(tmpdir: temp_dir) do |file|
+      file.binmode
+      yield file
+    end
+  end
 end

app/mailers/conversation_reply_mailer_attachment_helper.rb

@@ -0,0 +1,51 @@
+# Handles attachment processing for ConversationReplyMailer flows.
+module ConversationReplyMailerAttachmentHelper
+  private
+
+  def process_attachments_as_files_for_email_reply
+    # Attachment processing for direct email replies (when replying to a single message)
+    #
+    # How attachments are handled:
+    # 1. Total file size (<20MB): Added directly to the email as proper attachments
+    # 2. Total file size (>20MB): Added to @large_attachments to be displayed as links in the email
+
+    @options[:attachments] = []
+    @large_attachments = []
+    current_total_size = 0
+
+    @message.attachments.each do |attachment|
+      current_total_size = handle_attachment_inline(current_total_size, attachment)
+    end
+  end
+
+  def read_blob_content(blob)
+    buffer = +''
+    blob.open do |file|
+      while (chunk = file.read(64.kilobytes))
+        buffer << chunk
+      end
+    end
+    buffer
+  end
+
+  def handle_attachment_inline(current_total_size, attachment)
+    blob = attachment.file.blob
+    return current_total_size if blob.blank?
+
+    file_size = blob.byte_size
+    attachment_name = attachment.file.filename.to_s
+
+    if current_total_size + file_size <= 20.megabytes
+      content = read_blob_content(blob)
+      mail.attachments[attachment_name] = {
+        mime_type: attachment.file.content_type || 'application/octet-stream',
+        content: content
+      }
+      @options[:attachments] << { name: attachment_name }
+      current_total_size + file_size
+    else
+      @large_attachments << attachment
+      current_total_size
+    end
+  end
+end

app/mailers/conversation_reply_mailer_helper.rb

@@ -1,4 +1,6 @@
 module ConversationReplyMailerHelper
+  include ConversationReplyMailerAttachmentHelper
+
   def prepare_mail(cc_bcc_enabled)
     @options = {
       to: to_emails,
@@ -27,34 +29,6 @@ module ConversationReplyMailerHelper
     mail(@options)
   end
 
-  def process_attachments_as_files_for_email_reply
-    # Attachment processing for direct email replies (when replying to a single message)
-    #
-    # How attachments are handled:
-    # 1. Total file size (<20MB): Added directly to the email as proper attachments
-    # 2. Total file size (>20MB): Added to @large_attachments to be displayed as links in the email
-
-    @options[:attachments] = []
-    @large_attachments = []
-    current_total_size = 0
-
-    @message.attachments.each do |attachment|
-      raw_data = attachment.file.download
-      attachment_name = attachment.file.filename.to_s
-      file_size = raw_data.bytesize
-
-      # Attach files directly until we hit 20MB total
-      # After reaching 20MB, send remaining files as links
-      if current_total_size + file_size <= 20.megabytes
-        mail.attachments[attachment_name] = raw_data
-        @options[:attachments] << { name: attachment_name }
-        current_total_size += file_size
-      else
-        @large_attachments << attachment
-      end
-    end
-  end
-
   private
 
   def oauth_smtp_settings

app/models/attachment.rb

@@ -40,7 +40,7 @@ class Attachment < ApplicationRecord
   validate :acceptable_file
   validates :external_url, length: { maximum: Limits::URL_LENGTH_LIMIT }
   enum file_type: { :image => 0, :audio => 1, :video => 2, :file => 3, :location => 4, :fallback => 5, :share => 6, :story_mention => 7,
-                    :contact => 8, :ig_reel => 9 }
+                    :contact => 8, :ig_reel => 9, :ig_post => 10, :ig_story => 11 }
 
   def push_event_data
     return unless file_type

app/models/channel/telegram.rb

@@ -130,30 +130,39 @@ class Channel::Telegram < ApplicationRecord
   def convert_markdown_to_telegram_html(text)
     # ref: https://core.telegram.org/bots/api#html-style
 
-    # escape html tags in text. We are subbing \n to <br> since commonmark will strip exta '\n'
-    text = CGI.escapeHTML(text.gsub("\n", '<br>'))
+    # Escape HTML entities first to prevent HTML injection
+    # This ensures only markdown syntax is converted, not raw HTML
+    escaped_text = CGI.escapeHTML(text)
 
-    # convert markdown to html
-    html = CommonMarker.render_html(text).strip
+    # Parse markdown with extensions:
+    # - strikethrough: support ~~text~~
+    # - hardbreaks: preserve all newlines as <br>
+    html = CommonMarker.render_html(escaped_text, [:HARDBREAKS], [:strikethrough]).strip
 
-    # remove all html tags except b, strong, i, em, u, ins, s, strike, del, a, code, pre, blockquote
-    stripped_html = Rails::HTML5::SafeListSanitizer.new.sanitize(html, tags: %w[b strong i em u ins s strike del a code pre blockquote],
-                                                                       attributes: %w[href])
+    # Convert paragraph breaks to double newlines to preserve them
+    # CommonMarker creates <p> tags for paragraph breaks, but Telegram doesn't support <p>
+    html_with_breaks = html.gsub(%r{</p>\s*<p>}, "\n\n")
 
-    # converted escaped br tags to \n
-    stripped_html.gsub('&lt;br&gt;', "\n")
+    # Remove opening and closing <p> tags
+    html_with_breaks = html_with_breaks.gsub(%r{</?p>}, '')
+
+    # Sanitize to only allowed tags
+    stripped_html = Rails::HTML5::SafeListSanitizer.new.sanitize(html_with_breaks, tags: %w[b strong i em u ins s strike del a code pre blockquote],
+                                                                                   attributes: %w[href])
+
+    # Convert <br /> tags to newlines for Telegram
+    stripped_html.gsub(%r{<br\s*/?>}, "\n")
   end
 
   def message_request(chat_id, text, reply_markup = nil, reply_to_message_id = nil, business_connection_id: nil)
-    text_payload = convert_markdown_to_telegram_html(text)
-
+    # text is already converted to HTML by MessageContentPresenter
     business_body = {}
     business_body[:business_connection_id] = business_connection_id if business_connection_id
 
     HTTParty.post("#{telegram_api_url}/sendMessage",
                   body: {
                     chat_id: chat_id,
-                    text: text_payload,
+                    text: text,
                     reply_markup: reply_markup,
                     parse_mode: 'HTML',
                     reply_to_message_id: reply_to_message_id

app/models/integrations/app.rb

@@ -53,7 +53,7 @@ class Integrations::App
     when 'slack'
       GlobalConfigService.load('SLACK_CLIENT_SECRET', nil).present?
     when 'linear'
-      GlobalConfigService.load('LINEAR_CLIENT_ID', nil).present?
+      account.feature_enabled?('linear_integration') && GlobalConfigService.load('LINEAR_CLIENT_ID', nil).present?
     when 'shopify'
       shopify_enabled?(account)
     when 'leadsquared'

app/policies/account_policy.rb

@@ -30,4 +30,8 @@ class AccountPolicy < ApplicationPolicy
   def toggle_deletion?
     @account_user.administrator?
   end
+
+  def topup_checkout?
+    @account_user.administrator?
+  end
 end

app/presenters/message_content_presenter.rb

@@ -1,11 +1,18 @@
 class MessageContentPresenter < SimpleDelegator
   def outgoing_content
-    return content unless should_append_survey_link?
+    content_to_send = if should_append_survey_link?
+                        survey_link = survey_url(conversation.uuid)
+                        custom_message = inbox.csat_config&.dig('message')
+                        custom_message.present? ? "#{custom_message} #{survey_link}" : I18n.t('conversations.survey.response', link: survey_link)
+                      else
+                        content
+                      end
 
-    survey_link = survey_url(conversation.uuid)
-    custom_message = inbox.csat_config&.dig('message')
-
-    custom_message.present? ? "#{custom_message} #{survey_link}" : I18n.t('conversations.survey.response', link: survey_link)
+    Messages::MarkdownRendererService.new(
+      content_to_send,
+      conversation.inbox.channel_type,
+      conversation.inbox.channel
+    ).render
   end
 
   private

app/services/instagram/message_text.rb

@@ -59,11 +59,20 @@ class Instagram::MessageText < Instagram::BaseMessageText
     # We can safely create an unknown contact, making this integration work.
     return unknown_user(ig_scope_id) if error_code == 9010
 
+    # Handle error code 100: Object doesn't exist or missing permissions
+    # This typically occurs when trying to fetch a user that doesn't exist or has privacy restrictions
+    # We can safely create an unknown contact, similar to error 9010
+    return unknown_user(ig_scope_id) if error_code == 100
+
     Rails.logger.warn("[InstagramUserFetchError]: account_id #{@inbox.account_id} inbox_id #{@inbox.id} ig_scope_id #{ig_scope_id}")
     Rails.logger.warn("[InstagramUserFetchError]: #{error_message} #{error_code}")
 
     exception = StandardError.new("#{error_message} (Code: #{error_code}, IG Scope ID: #{ig_scope_id})")
     ChatwootExceptionTracker.new(exception, account: @inbox.account).capture_exception
+
+    # Explicitly return empty hash for any unhandled error codes
+    # This prevents the exception tracker result from being returned
+    {}
   end
 
   def base_uri

app/services/messages/markdown_renderer_service.rb

@@ -0,0 +1,74 @@
+class Messages::MarkdownRendererService
+  CHANNEL_RENDERERS = {
+    'Channel::Email' => :render_html,
+    'Channel::WebWidget' => :render_html,
+    'Channel::Telegram' => :render_telegram_html,
+    'Channel::Whatsapp' => :render_whatsapp,
+    'Channel::FacebookPage' => :render_instagram,
+    'Channel::Instagram' => :render_instagram,
+    'Channel::Line' => :render_line,
+    'Channel::TwitterProfile' => :render_plain_text,
+    'Channel::Sms' => :render_plain_text,
+    'Channel::TwilioSms' => :render_plain_text
+  }.freeze
+
+  def initialize(content, channel_type, channel = nil)
+    @content = content
+    @channel_type = channel_type
+    @channel = channel
+  end
+
+  def render
+    return @content if @content.blank?
+
+    renderer_method = CHANNEL_RENDERERS[effective_channel_type]
+    renderer_method ? send(renderer_method) : @content
+  end
+
+  private
+
+  def effective_channel_type
+    # For Twilio SMS channel, check if it's actually WhatsApp
+    if @channel_type == 'Channel::TwilioSms' && @channel&.whatsapp?
+      'Channel::Whatsapp'
+    else
+      @channel_type
+    end
+  end
+
+  def commonmarker_doc
+    @commonmarker_doc ||= CommonMarker.render_doc(@content, [:DEFAULT, :STRIKETHROUGH_DOUBLE_TILDE])
+  end
+
+  def render_html
+    markdown_renderer = BaseMarkdownRenderer.new
+    doc = CommonMarker.render_doc(@content, :DEFAULT, [:strikethrough])
+    markdown_renderer.render(doc)
+  end
+
+  def render_telegram_html
+    renderer = Messages::MarkdownRenderers::TelegramRenderer.new
+    doc = CommonMarker.render_doc(@content, [:STRIKETHROUGH_DOUBLE_TILDE], [:strikethrough])
+    renderer.render(doc).gsub(/\n+\z/, '')
+  end
+
+  def render_whatsapp
+    renderer = Messages::MarkdownRenderers::WhatsAppRenderer.new
+    renderer.render(commonmarker_doc).gsub(/\n+\z/, '')
+  end
+
+  def render_instagram
+    renderer = Messages::MarkdownRenderers::InstagramRenderer.new
+    renderer.render(commonmarker_doc).gsub(/\n+\z/, '')
+  end
+
+  def render_line
+    renderer = Messages::MarkdownRenderers::LineRenderer.new
+    renderer.render(commonmarker_doc).gsub(/\n+\z/, '')
+  end
+
+  def render_plain_text
+    renderer = Messages::MarkdownRenderers::PlainTextRenderer.new
+    renderer.render(commonmarker_doc).gsub(/\n+\z/, '')
+  end
+end

app/services/messages/markdown_renderers/base_markdown_renderer.rb

@@ -0,0 +1,39 @@
+class Messages::MarkdownRenderers::BaseMarkdownRenderer < CommonMarker::Renderer
+  def document(_node)
+    out(:children)
+  end
+
+  def paragraph(_node)
+    out(:children)
+    cr
+  end
+
+  def text(node)
+    out(node.string_content)
+  end
+
+  def softbreak(_node)
+    out(' ')
+  end
+
+  def linebreak(_node)
+    out("\n")
+  end
+
+  def strikethrough(_node)
+    out('<del>')
+    out(:children)
+    out('</del>')
+  end
+
+  def method_missing(method_name, node = nil, *args, **kwargs, &)
+    return super unless node.is_a?(CommonMarker::Node)
+
+    out(:children)
+    cr unless %i[text softbreak linebreak].include?(node.type)
+  end
+
+  def respond_to_missing?(_method_name, _include_private = false)
+    true
+  end
+end

app/services/messages/markdown_renderers/instagram_renderer.rb

@@ -0,0 +1,48 @@
+class Messages::MarkdownRenderers::InstagramRenderer < Messages::MarkdownRenderers::BaseMarkdownRenderer
+  def initialize
+    super
+    @list_item_number = 0
+  end
+
+  def strong(_node)
+    out('*', :children, '*')
+  end
+
+  def emph(_node)
+    out('_', :children, '_')
+  end
+
+  def code(node)
+    out(node.string_content)
+  end
+
+  def link(node)
+    out(node.url)
+  end
+
+  def list(node)
+    @list_type = node.list_type
+    @list_item_number = @list_type == :ordered_list ? node.list_start : 0
+    out(:children)
+    cr
+  end
+
+  def list_item(_node)
+    if @list_type == :ordered_list
+      out("#{@list_item_number}. ", :children)
+      @list_item_number += 1
+    else
+      out('- ', :children)
+    end
+    cr
+  end
+
+  def blockquote(_node)
+    out(:children)
+    cr
+  end
+
+  def softbreak(_node)
+    out("\n")
+  end
+end

app/services/messages/markdown_renderers/line_renderer.rb

@@ -0,0 +1,36 @@
+class Messages::MarkdownRenderers::LineRenderer < Messages::MarkdownRenderers::BaseMarkdownRenderer
+  def strong(_node)
+    out(' *', :children, '* ')
+  end
+
+  def emph(_node)
+    out(' _', :children, '_ ')
+  end
+
+  def code(node)
+    out(' `', node.string_content, '` ')
+  end
+
+  def link(node)
+    out(node.url)
+  end
+
+  def list(_node)
+    out(:children)
+    cr
+  end
+
+  def list_item(_node)
+    out(:children)
+    cr
+  end
+
+  def code_block(node)
+    out(' ```', "\n", node.string_content, '``` ', "\n")
+  end
+
+  def blockquote(_node)
+    out(:children)
+    cr
+  end
+end

app/services/messages/markdown_renderers/plain_text_renderer.rb

@@ -0,0 +1,62 @@
+class Messages::MarkdownRenderers::PlainTextRenderer < Messages::MarkdownRenderers::BaseMarkdownRenderer
+  def initialize
+    super
+    @list_item_number = 0
+  end
+
+  def link(node)
+    out(:children)
+    out(' ', node.url) if node.url.present?
+  end
+
+  def strong(_node)
+    out(:children)
+  end
+
+  def emph(_node)
+    out(:children)
+  end
+
+  def code(node)
+    out(node.string_content)
+  end
+
+  def list(node)
+    @list_type = node.list_type
+    @list_item_number = @list_type == :ordered_list ? node.list_start : 0
+    out(:children)
+    cr
+  end
+
+  def list_item(_node)
+    if @list_type == :ordered_list
+      out("#{@list_item_number}. ", :children)
+      @list_item_number += 1
+    else
+      out('- ', :children)
+    end
+    cr
+  end
+
+  def blockquote(_node)
+    out(:children)
+    cr
+  end
+
+  def code_block(node)
+    out(node.string_content, "\n")
+  end
+
+  def header(_node)
+    out(:children)
+    cr
+  end
+
+  def thematic_break(_node)
+    out("\n")
+  end
+
+  def softbreak(_node)
+    out("\n")
+  end
+end

app/services/messages/markdown_renderers/telegram_renderer.rb

@@ -0,0 +1,60 @@
+class Messages::MarkdownRenderers::TelegramRenderer < Messages::MarkdownRenderers::BaseMarkdownRenderer
+  def initialize
+    super
+    @list_item_number = 0
+  end
+
+  def strong(_node)
+    out('<strong>', :children, '</strong>')
+  end
+
+  def emph(_node)
+    out('<em>', :children, '</em>')
+  end
+
+  def code(node)
+    out('<code>', node.string_content, '</code>')
+  end
+
+  def link(node)
+    out('<a href="', node.url, '">', :children, '</a>')
+  end
+
+  def strikethrough(_node)
+    out('<del>', :children, '</del>')
+  end
+
+  def blockquote(_node)
+    out('<blockquote>', :children, '</blockquote>')
+  end
+
+  def code_block(node)
+    out('<pre>', node.string_content, '</pre>')
+  end
+
+  def list(node)
+    @list_type = node.list_type
+    @list_item_number = @list_type == :ordered_list ? node.list_start : 0
+    out(:children)
+    cr
+  end
+
+  def list_item(_node)
+    if @list_type == :ordered_list
+      out("#{@list_item_number}. ", :children)
+      @list_item_number += 1
+    else
+      out('• ', :children)
+    end
+    cr
+  end
+
+  def header(_node)
+    out('<strong>', :children, '</strong>')
+    cr
+  end
+
+  def softbreak(_node)
+    out("\n")
+  end
+end

app/services/messages/markdown_renderers/whats_app_renderer.rb

@@ -0,0 +1,36 @@
+class Messages::MarkdownRenderers::WhatsAppRenderer < Messages::MarkdownRenderers::BaseMarkdownRenderer
+  def strong(_node)
+    out('*', :children, '*')
+  end
+
+  def emph(_node)
+    out('_', :children, '_')
+  end
+
+  def code(node)
+    out('`', node.string_content, '`')
+  end
+
+  def link(node)
+    out(node.url)
+  end
+
+  def list(_node)
+    out(:children)
+    cr
+  end
+
+  def list_item(_node)
+    out('- ', :children)
+    cr
+  end
+
+  def blockquote(_node)
+    out('> ', :children)
+    cr
+  end
+
+  def softbreak(_node)
+    out("\n")
+  end
+end

app/services/telegram/send_attachments_service.rb

@@ -96,11 +96,16 @@ class Telegram::SendAttachmentsService
   # Telegram picks up the file name from original field name, so we need to save the file with the original name.
   # Hence not using Tempfile here.
   def save_attachment_to_tempfile(attachment)
-    raw_data = attachment.file.download
-    temp_dir = Rails.root.join('tmp/uploads')
+    temp_dir = Rails.root.join('tmp/uploads', "telegram-#{attachment.message_id}")
     FileUtils.mkdir_p(temp_dir)
     temp_file_path = File.join(temp_dir, attachment.file.filename.to_s)
-    File.write(temp_file_path, raw_data, mode: 'wb')
+
+    File.open(temp_file_path, 'wb') do |file|
+      attachment.file.blob.open do |blob_file|
+        IO.copy_stream(blob_file, file)
+      end
+    end
+
     temp_file_path
   end
 

app/views/api/v1/widget/inbox_members/index.json.jbuilder

@@ -3,6 +3,6 @@ json.payload do
     json.id inbox_member.user.id
     json.name inbox_member.user.available_name
     json.avatar_url inbox_member.user.avatar_url
-    json.availability_status inbox_member.user.account_users.find_by(account_id: @current_account.id).availability_status
+    json.availability_status inbox_member.user.account_users.find_by(account_id: @current_account.id)&.availability_status
   end
 end

app/views/mailers/conversation_reply_mailer/email_reply.html.erb

@@ -1,7 +1,7 @@
 <% if @message.content_attributes.dig('email', 'html_content', 'reply').present? %>
 <%= @message.content_attributes.dig('email', 'html_content', 'reply').html_safe %>
 <% elsif @message.content %>
-<%= ChatwootMarkdownRenderer.new(@message.outgoing_content).render_message %>
+<%= @message.outgoing_content.html_safe %>
 <% end %>
 <% if @large_attachments.present? %>
 <p>Attachments:</p>

config/locales/en.yml

@@ -122,6 +122,13 @@ en:
       invalid_token: Invalid or expired MFA token
       invalid_credentials: Invalid credentials or verification code
       feature_unavailable: MFA feature is not available. Please configure encryption keys.
+    topup:
+      credits_required: Credits amount is required
+      invalid_credits: Invalid credits amount
+      invalid_option: Invalid topup option
+      plan_not_eligible: Top-ups are only available for paid plans. Please upgrade your plan first.
+      stripe_customer_not_configured: Stripe customer not configured
+      no_payment_method: No payment methods found. Please add a payment method before making a purchase.
   profile:
     mfa:
       enabled: MFA enabled successfully
@@ -197,6 +204,8 @@ en:
     messages:
       instagram_story_content: '%{story_sender} mentioned you in the story: '
       instagram_deleted_story_content: This story is no longer available.
+      instagram_shared_story_content: 'Shared story'
+      instagram_shared_post_content: 'Shared post'
       deleted: This message was deleted
       whatsapp:
         list_button_label: 'Choose an item'

config/routes.rb

@@ -438,6 +438,7 @@ Rails.application.routes.draw do
               post :subscription
               get :limits
               post :toggle_deletion
+              post :topup_checkout
             end
           end
         end

enterprise/app/controllers/enterprise/api/v1/accounts_controller.rb

@@ -55,6 +55,22 @@ class Enterprise::Api::V1::AccountsController < Api::BaseController
     end
   end
 
+  def topup_checkout
+    return render json: { error: I18n.t('errors.topup.credits_required') }, status: :unprocessable_entity if params[:credits].blank?
+
+    service = Enterprise::Billing::TopupCheckoutService.new(account: @account)
+    result = service.create_checkout_session(credits: params[:credits].to_i)
+
+    @account.reload
+    render json: result.merge(
+      id: @account.id,
+      limits: @account.limits,
+      custom_attributes: @account.custom_attributes
+    )
+  rescue Enterprise::Billing::TopupCheckoutService::Error, Stripe::StripeError => e
+    render_could_not_create_error(e.message)
+  end
+
   private
 
   def check_cloud_env

enterprise/app/helpers/captain/chat_helper.rb

@@ -1,31 +1,83 @@
 module Captain::ChatHelper
   include Integrations::LlmInstrumentation
-  include Captain::ToolExecutionHelper
+  include Captain::ChatResponseHelper
 
   def request_chat_completion
     log_chat_completion_request
 
+    chat = build_chat
+
+    add_messages_to_chat(chat)
     with_agent_session do
-      response = instrument_llm_call(instrumentation_params) do
-        @client.chat(
-          parameters: chat_parameters
-        )
-      end
-      handle_response(response)
+      response = chat.ask(conversation_messages.last[:content])
+      build_response(response)
     end
   rescue StandardError => e
     Rails.logger.error "#{self.class.name} Assistant: #{@assistant.id}, Error in chat completion: #{e}"
     raise e
   end
 
-  def instrumentation_params
+  private
+
+  def build_chat
+    llm_chat = chat(model: @model, temperature: temperature)
+    llm_chat.with_params(response_format: { type: 'json_object' })
+
+    llm_chat = setup_tools(llm_chat)
+    setup_system_instructions(llm_chat)
+    setup_event_handlers(llm_chat)
+
+    llm_chat
+  end
+
+  def setup_tools(chat)
+    @tools&.each do |tool|
+      chat.with_tool(tool)
+    end
+    chat
+  end
+
+  def setup_system_instructions(chat)
+    system_messages = @messages.select { |m| m[:role] == 'system' || m[:role] == :system }
+    combined_instructions = system_messages.pluck(:content).join("\n\n")
+    chat.with_instructions(combined_instructions)
+  end
+
+  def setup_event_handlers(chat)
+    chat.on_new_message { start_llm_turn_span(instrumentation_params(chat)) }
+    chat.on_end_message { |message| end_llm_turn_span(message) }
+    chat.on_tool_call { |tool_call| handle_tool_call(tool_call) }
+    chat.on_tool_result { |result| handle_tool_result(result) }
+
+    chat
+  end
+
+  def handle_tool_call(tool_call)
+    persist_thinking_message(tool_call)
+    start_tool_span(tool_call)
+    @pending_tool_calls ||= []
+    @pending_tool_calls.push(tool_call)
+  end
+
+  def handle_tool_result(result)
+    end_tool_span(result)
+    persist_tool_completion
+  end
+
+  def add_messages_to_chat(chat)
+    conversation_messages[0...-1].each do |msg|
+      chat.add_message(role: msg[:role].to_sym, content: msg[:content])
+    end
+  end
+
+  def instrumentation_params(chat = nil)
     {
       span_name: "llm.captain.#{feature_name}",
       account_id: resolved_account_id,
       conversation_id: @conversation_id,
       feature_name: feature_name,
       model: @model,
-      messages: @messages,
+      messages: chat ? chat.messages.map { |m| { role: m.role.to_s, content: m.content.to_s } } : @messages,
       temperature: temperature,
       metadata: {
         assistant_id: @assistant&.id
@@ -33,14 +85,8 @@ module Captain::ChatHelper
     }
   end
 
-  def chat_parameters
-    {
-      model: @model,
-      messages: @messages,
-      tools: @tool_registry&.registered_tools || [],
-      response_format: { type: 'json_object' },
-      temperature: temperature
-    }
+  def conversation_messages
+    @messages.reject { |m| m[:role] == 'system' || m[:role] == :system }
   end
 
   def temperature
@@ -51,8 +97,6 @@ module Captain::ChatHelper
     @account&.id || @assistant&.account_id
   end
 
-  private
-
   # Ensures all LLM calls and tool executions within an agentic loop
   # are grouped under a single trace/session in Langfuse.
   #
@@ -78,7 +122,7 @@ module Captain::ChatHelper
   def log_chat_completion_request
     Rails.logger.info(
       "#{self.class.name} Assistant: #{@assistant.id}, Requesting chat completion
-      for messages #{@messages} with #{@tool_registry&.registered_tools&.length || 0} tools
+      for messages #{@messages} with #{@tools&.length || 0} tools
       "
     )
   end

enterprise/app/helpers/captain/chat_response_helper.rb

@@ -0,0 +1,52 @@
+module Captain::ChatResponseHelper
+  private
+
+  def build_response(response)
+    Rails.logger.debug { "#{self.class.name} Assistant: #{@assistant.id}, Received response #{response}" }
+
+    parsed = parse_json_response(response.content)
+
+    persist_message(parsed, 'assistant')
+    parsed
+  end
+
+  def parse_json_response(content)
+    content = content.gsub('```json', '').gsub('```', '')
+    content = content.strip
+    JSON.parse(content)
+  rescue JSON::ParserError => e
+    Rails.logger.error "#{self.class.name} Assistant: #{@assistant.id}, Error parsing JSON response: #{e.message}"
+    { 'content' => content }
+  end
+
+  def persist_thinking_message(tool_call)
+    return if @copilot_thread.blank?
+
+    tool_name = tool_call.name.to_s
+
+    persist_message(
+      {
+        'content' => "Using #{tool_name}",
+        'function_name' => tool_name
+      },
+      'assistant_thinking'
+    )
+  end
+
+  def persist_tool_completion
+    return if @copilot_thread.blank?
+
+    tool_call = @pending_tool_calls&.pop
+    return unless tool_call
+
+    tool_name = tool_call.name.to_s
+
+    persist_message(
+      {
+        'content' => "Completed #{tool_name}",
+        'function_name' => tool_name
+      },
+      'assistant_thinking'
+    )
+  end
+end

enterprise/app/helpers/captain/tool_execution_helper.rb

@@ -1,83 +0,0 @@
-module Captain::ToolExecutionHelper
-  private
-
-  def handle_response(response)
-    Rails.logger.debug { "#{self.class.name} Assistant: #{@assistant.id}, Received response #{response}" }
-    message = response.dig('choices', 0, 'message')
-
-    if message['tool_calls']
-      process_tool_calls(message['tool_calls'])
-    else
-      message = JSON.parse(message['content'].strip)
-      persist_message(message, 'assistant')
-      message
-    end
-  end
-
-  def process_tool_calls(tool_calls)
-    append_tool_calls(tool_calls)
-    tool_calls.each { |tool_call| process_tool_call(tool_call) }
-    request_chat_completion
-  end
-
-  def process_tool_call(tool_call)
-    arguments = JSON.parse(tool_call['function']['arguments'])
-    function_name = tool_call['function']['name']
-    tool_call_id = tool_call['id']
-
-    if @tool_registry.respond_to?(function_name)
-      execute_tool(function_name, arguments, tool_call_id)
-    else
-      process_invalid_tool_call(function_name, tool_call_id)
-    end
-  end
-
-  def execute_tool(function_name, arguments, tool_call_id)
-    persist_tool_status(function_name, 'captain.copilot.using_tool')
-    result = perform_tool_call(function_name, arguments)
-    persist_tool_status(function_name, 'captain.copilot.completed_tool_call')
-    append_tool_response(result, tool_call_id)
-  end
-
-  def perform_tool_call(function_name, arguments)
-    instrument_tool_call(function_name, arguments) do
-      @tool_registry.send(function_name, arguments)
-    end
-  rescue StandardError => e
-    Rails.logger.error "Tool #{function_name} failed: #{e.message}"
-    "Error executing #{function_name}: #{e.message}"
-  end
-
-  def persist_tool_status(function_name, translation_key)
-    persist_message(
-      {
-        content: I18n.t(translation_key, function_name: function_name),
-        function_name: function_name
-      },
-      'assistant_thinking'
-    )
-  end
-
-  def append_tool_calls(tool_calls)
-    @messages << {
-      role: 'assistant',
-      tool_calls: tool_calls
-    }
-  end
-
-  def process_invalid_tool_call(function_name, tool_call_id)
-    persist_message(
-      { content: I18n.t('captain.copilot.invalid_tool_call'), function_name: function_name },
-      'assistant_thinking'
-    )
-    append_tool_response(I18n.t('captain.copilot.tool_not_available'), tool_call_id)
-  end
-
-  def append_tool_response(content, tool_call_id)
-    @messages << {
-      role: 'tool',
-      tool_call_id: tool_call_id,
-      content: content
-    }
-  end
-end

enterprise/app/services/captain/copilot/chat_service.rb

@@ -1,6 +1,4 @@
-require 'openai'
-
-class Captain::Copilot::ChatService < Llm::BaseOpenAiService
+class Captain::Copilot::ChatService < Llm::BaseAiService
   include Captain::ChatHelper
 
   attr_reader :assistant, :account, :user, :copilot_thread, :previous_history, :messages
@@ -14,9 +12,10 @@ class Captain::Copilot::ChatService < Llm::BaseOpenAiService
     @copilot_thread = nil
     @previous_history = []
     @conversation_id = config[:conversation_id]
+
     setup_user(config)
     setup_message_history(config)
-    register_tools
+    @tools = build_tools
     @messages = build_messages(config)
   end
 
@@ -60,16 +59,19 @@ class Captain::Copilot::ChatService < Llm::BaseOpenAiService
                         end
   end
 
-  def register_tools
-    @tool_registry = Captain::ToolRegistryService.new(@assistant, user: @user)
-    @tool_registry.register_tool(Captain::Tools::SearchDocumentationService)
-    @tool_registry.register_tool(Captain::Tools::Copilot::GetArticleService)
-    @tool_registry.register_tool(Captain::Tools::Copilot::GetContactService)
-    @tool_registry.register_tool(Captain::Tools::Copilot::GetConversationService)
-    @tool_registry.register_tool(Captain::Tools::Copilot::SearchArticlesService)
-    @tool_registry.register_tool(Captain::Tools::Copilot::SearchContactsService)
-    @tool_registry.register_tool(Captain::Tools::Copilot::SearchConversationsService)
-    @tool_registry.register_tool(Captain::Tools::Copilot::SearchLinearIssuesService)
+  def build_tools
+    tools = []
+
+    tools << Captain::Tools::SearchDocumentationService.new(@assistant, user: @user)
+    tools << Captain::Tools::Copilot::GetConversationService.new(@assistant, user: @user)
+    tools << Captain::Tools::Copilot::SearchConversationsService.new(@assistant, user: @user)
+    tools << Captain::Tools::Copilot::GetContactService.new(@assistant, user: @user)
+    tools << Captain::Tools::Copilot::GetArticleService.new(@assistant, user: @user)
+    tools << Captain::Tools::Copilot::SearchArticlesService.new(@assistant, user: @user)
+    tools << Captain::Tools::Copilot::SearchContactsService.new(@assistant, user: @user)
+    tools << Captain::Tools::Copilot::SearchLinearIssuesService.new(@assistant, user: @user)
+
+    tools.select(&:active?)
   end
 
   def system_message
@@ -77,12 +79,16 @@ class Captain::Copilot::ChatService < Llm::BaseOpenAiService
       role: 'system',
       content: Captain::Llm::SystemPromptsService.copilot_response_generator(
         @assistant.config['product_name'],
-        @tool_registry.tools_summary,
+        tools_summary,
         @assistant.config
       )
     }
   end
 
+  def tools_summary
+    @tools.map { |tool| "- #{tool.class.name}: #{tool.class.description}" }.join("\n")
+  end
+
   def account_id_context
     {
       role: 'system',

enterprise/app/services/captain/llm/assistant_chat_service.rb

@@ -1,6 +1,4 @@
-require 'openai'
-
-class Captain::Llm::AssistantChatService < Llm::BaseOpenAiService
+class Captain::Llm::AssistantChatService < Llm::BaseAiService
   include Captain::ChatHelper
 
   def initialize(assistant: nil, conversation_id: nil)
@@ -8,9 +6,10 @@ class Captain::Llm::AssistantChatService < Llm::BaseOpenAiService
 
     @assistant = assistant
     @conversation_id = conversation_id
+
     @messages = [system_message]
     @response = ''
-    register_tools
+    @tools = build_tools
   end
 
   # additional_message: A single message (String) from the user that should be appended to the chat.
@@ -28,9 +27,8 @@ class Captain::Llm::AssistantChatService < Llm::BaseOpenAiService
 
   private
 
-  def register_tools
-    @tool_registry = Captain::ToolRegistryService.new(@assistant, user: nil)
-    @tool_registry.register_tool(Captain::Tools::SearchDocumentationService)
+  def build_tools
+    [Captain::Tools::SearchDocumentationService.new(@assistant, user: nil)]
   end
 
   def system_message

enterprise/app/services/captain/llm/contact_attributes_service.rb

@@ -1,4 +1,4 @@
-class Captain::Llm::ContactAttributesService < Llm::BaseOpenAiService
+class Captain::Llm::ContactAttributesService < Llm::LegacyBaseOpenAiService
   def initialize(assistant, conversation)
     super()
     @assistant = assistant

enterprise/app/services/captain/llm/contact_notes_service.rb

@@ -1,4 +1,4 @@
-class Captain::Llm::ContactNotesService < Llm::BaseOpenAiService
+class Captain::Llm::ContactNotesService < Llm::LegacyBaseOpenAiService
   def initialize(assistant, conversation)
     super()
     @assistant = assistant

enterprise/app/services/captain/llm/conversation_faq_service.rb

@@ -1,4 +1,4 @@
-class Captain::Llm::ConversationFaqService < Llm::BaseOpenAiService
+class Captain::Llm::ConversationFaqService < Llm::LegacyBaseOpenAiService
   DISTANCE_THRESHOLD = 0.3
 
   def initialize(assistant, conversation)

enterprise/app/services/captain/llm/embedding_service.rb

@@ -1,6 +1,6 @@
 require 'openai'
 
-class Captain::Llm::EmbeddingService < Llm::BaseOpenAiService
+class Captain::Llm::EmbeddingService < Llm::LegacyBaseOpenAiService
   class EmbeddingsError < StandardError; end
 
   def self.embedding_model

enterprise/app/services/captain/llm/faq_generator_service.rb

@@ -1,4 +1,4 @@
-class Captain::Llm::FaqGeneratorService < Llm::BaseOpenAiService
+class Captain::Llm::FaqGeneratorService < Llm::LegacyBaseOpenAiService
   def initialize(content, language = 'english')
     super()
     @language = language

enterprise/app/services/captain/llm/paginated_faq_generator_service.rb

@@ -1,4 +1,4 @@
-class Captain::Llm::PaginatedFaqGeneratorService < Llm::BaseOpenAiService
+class Captain::Llm::PaginatedFaqGeneratorService < Llm::LegacyBaseOpenAiService
   # Default pages per chunk - easily configurable
   DEFAULT_PAGES_PER_CHUNK = 10
   MAX_ITERATIONS = 20 # Safety limit to prevent infinite loops

enterprise/app/services/captain/llm/pdf_processing_service.rb

@@ -1,4 +1,4 @@
-class Captain::Llm::PdfProcessingService < Llm::BaseOpenAiService
+class Captain::Llm::PdfProcessingService < Llm::LegacyBaseOpenAiService
   def initialize(document)
     super()
     @document = document
@@ -29,12 +29,16 @@ class Captain::Llm::PdfProcessingService < Llm::BaseOpenAiService
     end
   end
 
-  def with_tempfile(&)
+  def with_tempfile
     Tempfile.create(['pdf_upload', '.pdf'], binmode: true) do |temp_file|
-      temp_file.write(document.pdf_file.download)
-      temp_file.close
+      document.pdf_file.blob.open do |blob_file|
+        IO.copy_stream(blob_file, temp_file)
+      end
 
-      File.open(temp_file.path, 'rb', &)
+      temp_file.flush
+      temp_file.rewind
+
+      yield temp_file
     end
   end
 end

enterprise/app/services/captain/onboarding/website_analyzer_service.rb

@@ -1,4 +1,4 @@
-class Captain::Onboarding::WebsiteAnalyzerService < Llm::BaseOpenAiService
+class Captain::Onboarding::WebsiteAnalyzerService < Llm::LegacyBaseOpenAiService
   MAX_CONTENT_LENGTH = 8000
 
   def initialize(website_url)

enterprise/app/services/captain/tools/base_tool.rb

@@ -0,0 +1,26 @@
+class Captain::Tools::BaseTool < RubyLLM::Tool
+  attr_accessor :assistant
+
+  def initialize(assistant, user: nil)
+    @assistant = assistant
+    @user = user
+    super()
+  end
+
+  def active?
+    true
+  end
+
+  private
+
+  def user_has_permission(permission)
+    return false if @user.blank?
+
+    account_user = AccountUser.find_by(account_id: @assistant.account_id, user_id: @user.id)
+    return false if account_user.blank?
+
+    return account_user.custom_role.permissions.include?(permission) if account_user.custom_role.present?
+
+    account_user.administrator? || account_user.agent?
+  end
+end

enterprise/app/services/captain/tools/copilot/get_article_service.rb

@@ -1,32 +1,11 @@
-class Captain::Tools::Copilot::GetArticleService < Captain::Tools::BaseService
-  def name
+class Captain::Tools::Copilot::GetArticleService < Captain::Tools::BaseTool
+  def self.name
     'get_article'
   end
+  description 'Get details of an article including its content and metadata'
+  param :article_id, type: :number, desc: 'The ID of the article to retrieve', required: true
 
-  def description
-    'Get details of an article including its content and metadata'
-  end
-
-  def parameters
-    {
-      type: 'object',
-      properties: {
-        article_id: {
-          type: 'number',
-          description: 'The ID of the article to retrieve'
-        }
-      },
-      required: %w[article_id]
-    }
-  end
-
-  def execute(arguments)
-    article_id = arguments['article_id']
-
-    Rails.logger.info { "#{self.class.name}: Article ID: #{article_id}" }
-
-    return 'Missing required parameters' if article_id.blank?
-
+  def execute(article_id:)
     article = Article.find_by(id: article_id, account_id: @assistant.account_id)
     return 'Article not found' if article.nil?
 

enterprise/app/services/captain/tools/copilot/get_contact_service.rb

@@ -1,32 +1,11 @@
-class Captain::Tools::Copilot::GetContactService < Captain::Tools::BaseService
-  def name
+class Captain::Tools::Copilot::GetContactService < Captain::Tools::BaseTool
+  def self.name
     'get_contact'
   end
+  description 'Get details of a contact including their profile information'
+  param :contact_id, type: :number, desc: 'The ID of the contact to retrieve', required: true
 
-  def description
-    'Get details of a contact including their profile information'
-  end
-
-  def parameters
-    {
-      type: 'object',
-      properties: {
-        contact_id: {
-          type: 'number',
-          description: 'The ID of the contact to retrieve'
-        }
-      },
-      required: %w[contact_id]
-    }
-  end
-
-  def execute(arguments)
-    contact_id = arguments['contact_id']
-
-    Rails.logger.info "#{self.class.name}: Contact ID: #{contact_id}"
-
-    return 'Missing required parameters' if contact_id.blank?
-
+  def execute(contact_id:)
     contact = Contact.find_by(id: contact_id, account_id: @assistant.account_id)
     return 'Contact not found' if contact.nil?
 

enterprise/app/services/captain/tools/copilot/get_conversation_service.rb

@@ -1,32 +1,12 @@
-class Captain::Tools::Copilot::GetConversationService < Captain::Tools::BaseService
-  def name
+class Captain::Tools::Copilot::GetConversationService < Captain::Tools::BaseTool
+  def self.name
     'get_conversation'
   end
+  description 'Get details of a conversation including messages and contact information'
 
-  def description
-    'Get details of a conversation including messages and contact information'
-  end
-
-  def parameters
-    {
-      type: 'object',
-      properties: {
-        conversation_id: {
-          type: 'number',
-          description: 'The ID of the conversation to retrieve'
-        }
-      },
-      required: %w[conversation_id]
-    }
-  end
-
-  def execute(arguments)
-    conversation_id = arguments['conversation_id']
-
-    Rails.logger.info "#{self.class.name}: Conversation ID: #{conversation_id}"
-
-    return 'Missing required parameters' if conversation_id.blank?
+  param :conversation_id, type: :integer, desc: 'ID of the conversation to retrieve', required: true
 
+  def execute(conversation_id:)
     conversation = Conversation.find_by(display_id: conversation_id, account_id: @assistant.account_id)
     return 'Conversation not found' if conversation.blank?
 

enterprise/app/services/captain/tools/copilot/search_articles_service.rb

@@ -1,36 +1,18 @@
-class Captain::Tools::Copilot::SearchArticlesService < Captain::Tools::BaseService
-  def name
+class Captain::Tools::Copilot::SearchArticlesService < Captain::Tools::BaseTool
+  def self.name
     'search_articles'
   end
+  description 'Search articles based on parameters'
+  param :query, desc: 'Search articles by title or content (partial match)', required: false
+  param :category_id, type: :number, desc: 'Filter articles by category ID', required: false
+  param :status, type: :string, desc: 'Filter articles by status - MUST BE ONE OF: draft, published, archived', required: false
 
-  def description
-    'Search articles based on parameters'
-  end
-
-  def parameters
-    {
-      type: 'object',
-      properties: properties,
-      required: ['query']
-    }
-  end
-
-  def execute(arguments)
-    query = arguments['query']
-    category_id = arguments['category_id']
-    status = arguments['status']
-
-    Rails.logger.info "#{self.class.name}: Query: #{query}, Category ID: #{category_id}, Status: #{status}"
-
-    return 'Missing required parameters' if query.blank?
-
-    articles = fetch_articles(query, category_id, status)
-
+  def execute(query: nil, category_id: nil, status: nil)
+    articles = fetch_articles(query: query, category_id: category_id, status: status)
     return 'No articles found' unless articles.exists?
 
     total_count = articles.count
     articles = articles.limit(100)
-
     <<~RESPONSE
       #{total_count > 100 ? "Found #{total_count} articles (showing first 100)" : "Total number of articles: #{total_count}"}
       #{articles.map(&:to_llm_text).join("\n---\n")}
@@ -43,29 +25,11 @@ class Captain::Tools::Copilot::SearchArticlesService < Captain::Tools::BaseServi
 
   private
 
-  def fetch_articles(query, category_id, status)
+  def fetch_articles(query:, category_id:, status:)
     articles = Article.where(account_id: @assistant.account_id)
     articles = articles.where('title ILIKE :query OR content ILIKE :query', query: "%#{query}%") if query.present?
     articles = articles.where(category_id: category_id) if category_id.present?
     articles = articles.where(status: status) if status.present?
     articles
   end
-
-  def properties
-    {
-      query: {
-        type: 'string',
-        description: 'Search articles by title or content (partial match)'
-      },
-      category_id: {
-        type: 'number',
-        description: 'Filter articles by category ID'
-      },
-      status: {
-        type: 'string',
-        enum: %w[draft published archived],
-        description: 'Filter articles by status'
-      }
-    }
-  end
 end

enterprise/app/services/captain/tools/copilot/search_contacts_service.rb

@@ -1,27 +1,14 @@
-class Captain::Tools::Copilot::SearchContactsService < Captain::Tools::BaseService
-  def name
+class Captain::Tools::Copilot::SearchContactsService < Captain::Tools::BaseTool
+  def self.name
     'search_contacts'
   end
 
-  def description
-    'Search contacts based on query parameters'
-  end
-
-  def parameters
-    {
-      type: 'object',
-      properties: properties,
-      required: []
-    }
-  end
-
-  def execute(arguments)
-    email = arguments['email']
-    phone_number = arguments['phone_number']
-    name = arguments['name']
-
-    Rails.logger.info "#{self.class.name} Email: #{email}, Phone Number: #{phone_number}, Name: #{name}"
+  description 'Search contacts based on query parameters'
+  param :email, type: :string, desc: 'Filter contacts by email'
+  param :phone_number, type: :string, desc: 'Filter contacts by phone number'
+  param :name, type: :string, desc: 'Filter contacts by name (partial match)'
 
+  def execute(email: nil, phone_number: nil, name: nil)
     contacts = Contact.where(account_id: @assistant.account_id)
     contacts = contacts.where(email: email) if email.present?
     contacts = contacts.where(phone_number: phone_number) if phone_number.present?
@@ -39,23 +26,4 @@ class Captain::Tools::Copilot::SearchContactsService < Captain::Tools::BaseServi
   def active?
     user_has_permission('contact_manage')
   end
-
-  private
-
-  def properties
-    {
-      email: {
-        type: 'string',
-        description: 'Filter contacts by email'
-      },
-      phone_number: {
-        type: 'string',
-        description: 'Filter contacts by phone number'
-      },
-      name: {
-        type: 'string',
-        description: 'Filter contacts by name (partial match)'
-      }
-    }
-  end
 end

enterprise/app/services/captain/tools/copilot/search_conversations_service.rb

@@ -1,26 +1,15 @@
-class Captain::Tools::Copilot::SearchConversationsService < Captain::Tools::BaseService
-  def name
-    'search_conversations'
+class Captain::Tools::Copilot::SearchConversationsService < Captain::Tools::BaseTool
+  def self.name
+    'search_conversation'
   end
+  description 'Search conversations based on parameters'
 
-  def description
-    'Search conversations based on parameters'
-  end
-
-  def parameters
-    {
-      type: 'object',
-      properties: properties,
-      required: []
-    }
-  end
-
-  def execute(arguments)
-    status = arguments['status']
-    contact_id = arguments['contact_id']
-    priority = arguments['priority']
-    labels = arguments['labels']
+  param :status, type: :string, desc: 'Status of the conversation'
+  param :contact_id, type: :number, desc: 'Contact id'
+  param :priority, type: :string, desc: 'Priority of conversation'
+  param :labels, type: :string, desc: 'Labels available'
 
+  def execute(status: nil, contact_id: nil, priority: nil, labels: nil)
     conversations = get_conversations(status, contact_id, priority, labels)
 
     return 'No conversations found' unless conversations.exists?
@@ -58,13 +47,4 @@ class Captain::Tools::Copilot::SearchConversationsService < Captain::Tools::Base
       @assistant.account
     ).perform
   end
-
-  def properties
-    {
-      contact_id: { type: 'number', description: 'Filter conversations by contact ID' },
-      status: { type: 'string', enum: %w[open resolved pending snoozed], description: 'Filter conversations by status' },
-      priority: { type: 'string', enum: %w[low medium high urgent], description: 'Filter conversations by priority' },
-      labels: { type: 'array', items: { type: 'string' }, description: 'Filter conversations by labels' }
-    }
-  end
 end

enterprise/app/services/captain/tools/copilot/search_linear_issues_service.rb

@@ -1,34 +1,14 @@
-class Captain::Tools::Copilot::SearchLinearIssuesService < Captain::Tools::BaseService
-  def name
+class Captain::Tools::Copilot::SearchLinearIssuesService < Captain::Tools::BaseTool
+  def self.name
     'search_linear_issues'
   end
 
-  def description
-    'Search Linear issues based on a search term'
-  end
+  description 'Search Linear issues based on a search term'
+  param :term, type: :string, desc: 'The search term to find Linear issues', required: true
 
-  def parameters
-    {
-      type: 'object',
-      properties: {
-        term: {
-          type: 'string',
-          description: 'The search term to find Linear issues'
-        }
-      },
-      required: %w[term]
-    }
-  end
-
-  def execute(arguments)
+  def execute(term:)
     return 'Linear integration is not enabled' unless active?
 
-    term = arguments['term']
-
-    Rails.logger.info "#{self.class.name}: Service called with the search term #{term}"
-
-    return 'Missing required parameters' if term.blank?
-
     linear_service = Integrations::Linear::ProcessorService.new(account: @assistant.account)
     result = linear_service.search_issue(term)
 

enterprise/app/services/captain/tools/search_documentation_service.rb

@@ -1,27 +1,12 @@
-class Captain::Tools::SearchDocumentationService < Captain::Tools::BaseService
-  def name
+class Captain::Tools::SearchDocumentationService < Captain::Tools::BaseTool
+  def self.name
     'search_documentation'
   end
+  description 'Search and retrieve documentation from knowledge base'
 
-  def description
-    'Search and retrieve documentation from knowledge base'
-  end
+  param :query, desc: 'Search Query', required: true
 
-  def parameters
-    {
-      type: 'object',
-      properties: {
-        search_query: {
-          type: 'string',
-          description: 'The search query to look up in the documentation.'
-        }
-      },
-      required: ['search_query']
-    }
-  end
-
-  def execute(arguments)
-    query = arguments['search_query']
+  def execute(query:)
     Rails.logger.info { "#{self.class.name}: #{query}" }
 
     responses = assistant.responses.approved.search(query)

enterprise/app/services/enterprise/billing/handle_stripe_event_service.rb

@@ -1,5 +1,6 @@
 class Enterprise::Billing::HandleStripeEventService
   CLOUD_PLANS_CONFIG = 'CHATWOOT_CLOUD_PLANS'.freeze
+  CAPTAIN_CLOUD_PLAN_LIMITS = 'CAPTAIN_CLOUD_PLAN_LIMITS'.freeze
 
   # Plan hierarchy: Hacker (default) -> Startups -> Business -> Enterprise
   # Each higher tier includes all features from the lower tiers
@@ -46,23 +47,43 @@ class Enterprise::Billing::HandleStripeEventService
     # skipping self hosted plan events
     return if plan.blank? || account.blank?
 
+    previous_usage = capture_previous_usage
     update_account_attributes(subscription, plan)
     update_plan_features
-    reset_captain_usage
+
+    if billing_period_renewed?
+      ActiveRecord::Base.transaction do
+        handle_subscription_credits(plan, previous_usage)
+        account.reset_response_usage
+      end
+    elsif plan_changed?
+      handle_plan_change_credits(plan, previous_usage)
+    end
+  end
+
+  def capture_previous_usage
+    { responses: account.custom_attributes['captain_responses_usage'].to_i, monthly: current_plan_credits[:responses] }
+  end
+
+  def current_plan_credits
+    plan_name = account.custom_attributes['plan_name']
+    return { responses: 0, documents: 0 } if plan_name.blank?
+
+    get_plan_credits(plan_name)
   end
 
   def update_account_attributes(subscription, plan)
     # https://stripe.com/docs/api/subscriptions/object
     account.update(
-      custom_attributes: {
-        stripe_customer_id: subscription.customer,
-        stripe_price_id: subscription['plan']['id'],
-        stripe_product_id: subscription['plan']['product'],
-        plan_name: plan['name'],
-        subscribed_quantity: subscription['quantity'],
-        subscription_status: subscription['status'],
-        subscription_ends_on: Time.zone.at(subscription['current_period_end'])
-      }
+      custom_attributes: account.custom_attributes.merge(
+        'stripe_customer_id' => subscription.customer,
+        'stripe_price_id' => subscription['plan']['id'],
+        'stripe_product_id' => subscription['plan']['product'],
+        'plan_name' => plan['name'],
+        'subscribed_quantity' => subscription['quantity'],
+        'subscription_status' => subscription['status'],
+        'subscription_ends_on' => Time.zone.at(subscription['current_period_end'])
+      )
     )
   end
 
@@ -101,28 +122,47 @@ class Enterprise::Billing::HandleStripeEventService
     enable_plan_specific_features
   end
 
-  def reset_captain_usage
-    account.reset_response_usage
+  def handle_subscription_credits(plan, previous_usage)
+    current_limits = account.limits || {}
+
+    current_credits = current_limits['captain_responses'].to_i
+    new_plan_credits = get_plan_credits(plan['name'])[:responses]
+
+    consumed_topup_credits = [previous_usage[:responses] - previous_usage[:monthly], 0].max
+    updated_credits = current_credits - consumed_topup_credits - previous_usage[:monthly] + new_plan_credits
+
+    Rails.logger.info("Updating subscription credits for account #{account.id}: #{current_credits} -> #{updated_credits}")
+    account.update!(limits: current_limits.merge('captain_responses' => updated_credits))
+  end
+
+  def handle_plan_change_credits(new_plan, previous_usage)
+    current_limits = account.limits || {}
+    current_credits = current_limits['captain_responses'].to_i
+
+    previous_plan_credits = previous_usage[:monthly]
+    new_plan_credits = get_plan_credits(new_plan['name'])[:responses]
+
+    updated_credits = current_credits - previous_plan_credits + new_plan_credits
+
+    account.update!(limits: current_limits.merge('captain_responses' => updated_credits))
+  end
+
+  def get_plan_credits(plan_name)
+    config = InstallationConfig.find_by(name: CAPTAIN_CLOUD_PLAN_LIMITS).value
+    config = JSON.parse(config) if config.is_a?(String)
+    config[plan_name.downcase]&.symbolize_keys
   end
 
   def enable_plan_specific_features
     plan_name = account.custom_attributes['plan_name']
     return if plan_name.blank?
 
-    # Enable features based on plan hierarchy
     case plan_name
-    when 'Startups'
-      # Startups plan gets the basic features
-      account.enable_features(*STARTUP_PLAN_FEATURES)
+    when 'Startups' then account.enable_features(*STARTUP_PLAN_FEATURES)
     when 'Business'
-      # Business plan gets Startups features + Business features
-      account.enable_features(*STARTUP_PLAN_FEATURES)
-      account.enable_features(*BUSINESS_PLAN_FEATURES)
+      account.enable_features(*STARTUP_PLAN_FEATURES, *BUSINESS_PLAN_FEATURES)
     when 'Enterprise'
-      # Enterprise plan gets all features
-      account.enable_features(*STARTUP_PLAN_FEATURES)
-      account.enable_features(*BUSINESS_PLAN_FEATURES)
-      account.enable_features(*ENTERPRISE_PLAN_FEATURES)
+      account.enable_features(*STARTUP_PLAN_FEATURES, *BUSINESS_PLAN_FEATURES, *ENTERPRISE_PLAN_FEATURES)
     end
   end
 
@@ -130,6 +170,25 @@ class Enterprise::Billing::HandleStripeEventService
     @subscription ||= @event.data.object
   end
 
+  def previous_attributes
+    @previous_attributes ||= JSON.parse((@event.data.previous_attributes || {}).to_json)
+  end
+
+  def plan_changed?
+    return false if previous_attributes['plan'].blank?
+
+    previous_plan_id = previous_attributes.dig('plan', 'id')
+    current_plan_id = subscription['plan']['id']
+
+    previous_plan_id != current_plan_id
+  end
+
+  def billing_period_renewed?
+    return false if previous_attributes['current_period_start'].blank?
+
+    previous_attributes['current_period_start'] != subscription['current_period_start']
+  end
+
   def account
     @account ||= Account.where("custom_attributes->>'stripe_customer_id' = ?", subscription.customer).first
   end

enterprise/app/services/enterprise/billing/topup_checkout_service.rb

@@ -0,0 +1,95 @@
+class Enterprise::Billing::TopupCheckoutService
+  include BillingHelper
+
+  class Error < StandardError; end
+
+  TOPUP_OPTIONS = [
+    { credits: 1000, amount: 20.0, currency: 'usd' },
+    { credits: 2500, amount: 50.0, currency: 'usd' },
+    { credits: 6000, amount: 100.0, currency: 'usd' },
+    { credits: 12_000, amount: 200.0, currency: 'usd' }
+  ].freeze
+
+  pattr_initialize [:account!]
+
+  def create_checkout_session(credits:)
+    topup_option = validate_and_find_topup_option(credits)
+    charge_customer(topup_option, credits)
+    fulfill_credits(credits, topup_option)
+
+    {
+      credits: credits,
+      amount: topup_option[:amount],
+      currency: topup_option[:currency]
+    }
+  end
+
+  private
+
+  def validate_and_find_topup_option(credits)
+    raise Error, I18n.t('errors.topup.invalid_credits') unless credits.to_i.positive?
+    raise Error, I18n.t('errors.topup.plan_not_eligible') if default_plan?(account)
+    raise Error, I18n.t('errors.topup.stripe_customer_not_configured') if stripe_customer_id.blank?
+
+    topup_option = find_topup_option(credits)
+    raise Error, I18n.t('errors.topup.invalid_option') unless topup_option
+
+    # Validate payment method exists
+    validate_payment_method!
+
+    topup_option
+  end
+
+  def validate_payment_method!
+    customer = Stripe::Customer.retrieve(stripe_customer_id)
+
+    return if customer.invoice_settings.default_payment_method.present? || customer.default_source.present?
+
+    # Auto-set first payment method as default if available
+    payment_methods = Stripe::PaymentMethod.list(customer: stripe_customer_id, limit: 1)
+    raise Error, I18n.t('errors.topup.no_payment_method') if payment_methods.data.empty?
+
+    Stripe::Customer.update(stripe_customer_id, invoice_settings: { default_payment_method: payment_methods.data.first.id })
+  end
+
+  def charge_customer(topup_option, credits)
+    amount_cents = (topup_option[:amount] * 100).to_i
+    currency = topup_option[:currency]
+    description = "AI Credits Topup: #{credits} credits"
+
+    invoice = Stripe::Invoice.create(
+      customer: stripe_customer_id,
+      currency: currency,
+      collection_method: 'charge_automatically',
+      auto_advance: false,
+      description: description
+    )
+
+    Stripe::InvoiceItem.create(
+      customer: stripe_customer_id,
+      amount: amount_cents,
+      currency: currency,
+      invoice: invoice.id,
+      description: description
+    )
+
+    Stripe::Invoice.finalize_invoice(invoice.id, { auto_advance: false })
+    Stripe::Invoice.pay(invoice.id)
+  end
+
+  def fulfill_credits(credits, topup_option)
+    Enterprise::Billing::TopupFulfillmentService.new(account: account).fulfill(
+      credits: credits,
+      amount_cents: (topup_option[:amount] * 100).to_i,
+      currency: topup_option[:currency]
+    )
+  end
+
+  def stripe_customer_id
+    account.custom_attributes['stripe_customer_id']
+  end
+
+  def find_topup_option(credits)
+    TOPUP_OPTIONS.find { |opt| opt[:credits] == credits.to_i }
+  end
+end

enterprise/app/services/enterprise/billing/topup_fulfillment_service.rb

@@ -0,0 +1,51 @@
+class Enterprise::Billing::TopupFulfillmentService
+  pattr_initialize [:account!]
+
+  def fulfill(credits:, amount_cents:, currency:)
+    account.with_lock do
+      create_stripe_credit_grant(credits, amount_cents, currency)
+      update_account_credits(credits)
+    end
+
+    Rails.logger.info("Topup fulfilled for account #{account.id}: #{credits} credits, #{amount_cents} cents")
+  end
+
+  private
+
+  def create_stripe_credit_grant(credits, amount_cents, currency)
+    Stripe::Billing::CreditGrant.create(
+      customer: stripe_customer_id,
+      name: "Topup: #{credits} credits",
+      amount: {
+        type: 'monetary',
+        monetary: { currency: currency, value: amount_cents }
+      },
+      applicability_config: {
+        scope: { price_type: 'metered' }
+      },
+      category: 'paid',
+      expires_at: 6.months.from_now.to_i,
+      metadata: {
+        account_id: account.id.to_s,
+        source: 'topup',
+        credits: credits.to_s
+      }
+    )
+  end
+
+  def update_account_credits(credits)
+    current_limits = account.limits || {}
+    current_total = current_limits['captain_responses'].to_i
+    new_total = current_total + credits
+
+    account.update!(
+      limits: current_limits.merge(
+        'captain_responses' => new_total
+      )
+    )
+  end
+
+  def stripe_customer_id
+    account.custom_attributes['stripe_customer_id']
+  end
+end

enterprise/app/services/internal/account_analysis/content_evaluator_service.rb

@@ -1,4 +1,4 @@
-class Internal::AccountAnalysis::ContentEvaluatorService < Llm::BaseOpenAiService
+class Internal::AccountAnalysis::ContentEvaluatorService < Llm::LegacyBaseOpenAiService
   def initialize
     super()
 

enterprise/app/services/llm/base_ai_service.rb

@@ -0,0 +1,33 @@
+# frozen_string_literal: true
+
+# Base service for LLM operations using RubyLLM.
+# New features should inherit from this class.
+class Llm::BaseAiService
+  DEFAULT_MODEL = Llm::Config::DEFAULT_MODEL
+  DEFAULT_TEMPERATURE = 1.0
+
+  attr_reader :model, :temperature
+
+  def initialize
+    Llm::Config.initialize!
+    setup_model
+    setup_temperature
+  end
+
+  # Returns a configured RubyLLM chat instance.
+  # Subclasses can override model/temperature via instance variables or pass them explicitly.
+  def chat(model: @model, temperature: @temperature)
+    RubyLLM.chat(model: model).with_temperature(temperature)
+  end
+
+  private
+
+  def setup_model
+    config_value = InstallationConfig.find_by(name: 'CAPTAIN_OPEN_AI_MODEL')&.value
+    @model = (config_value.presence || DEFAULT_MODEL)
+  end
+
+  def setup_temperature
+    @temperature = DEFAULT_TEMPERATURE
+  end
+end

enterprise/app/services/llm/legacy_base_open_ai_service.rb

@@ -1,5 +1,11 @@
-class Llm::BaseOpenAiService
-  DEFAULT_MODEL = 'gpt-4o-mini'.freeze
+# frozen_string_literal: true
+
+# DEPRECATED: This class uses the legacy OpenAI Ruby gem directly.
+# New features should use Llm::BaseAiService with RubyLLM instead.
+# This class will be removed once all services are migrated to RubyLLM.
+class Llm::LegacyBaseOpenAiService
+  DEFAULT_MODEL = 'gpt-4o-mini'
+
   attr_reader :client, :model
 
   def initialize

enterprise/app/services/messages/audio_transcription_service.rb

@@ -1,4 +1,4 @@
-class Messages::AudioTranscriptionService < Llm::BaseOpenAiService
+class Messages::AudioTranscriptionService < Llm::LegacyBaseOpenAiService
   attr_reader :attachment, :message, :account
 
   def initialize(attachment)
@@ -27,10 +27,16 @@ class Messages::AudioTranscriptionService < Llm::BaseOpenAiService
   end
 
   def fetch_audio_file
-    temp_dir = Rails.root.join('tmp/uploads')
+    temp_dir = Rails.root.join('tmp/uploads/audio-transcriptions')
     FileUtils.mkdir_p(temp_dir)
-    temp_file_path = File.join(temp_dir, attachment.file.filename.to_s)
-    File.write(temp_file_path, attachment.file.download, mode: 'wb')
+    temp_file_path = File.join(temp_dir, "#{attachment.file.blob.key}-#{attachment.file.filename}")
+
+    File.open(temp_file_path, 'wb') do |file|
+      attachment.file.blob.open do |blob_file|
+        IO.copy_stream(blob_file, file)
+      end
+    end
+
     temp_file_path
   end
 
@@ -40,18 +46,24 @@ class Messages::AudioTranscriptionService < Llm::BaseOpenAiService
 
     temp_file_path = fetch_audio_file
 
-    response = @client.audio.transcribe(
-      parameters: {
-        model: 'whisper-1',
-        file: File.open(temp_file_path),
-        temperature: 0.4
-      }
-    )
+    response_text = nil
+
+    File.open(temp_file_path, 'rb') do |file|
+      response = @client.audio.transcribe(
+        parameters: {
+          model: 'whisper-1',
+          file: file,
+          temperature: 0.4
+        }
+      )
+
+      response_text = response['text']
+    end
 
     FileUtils.rm_f(temp_file_path)
 
-    update_transcription(response['text'])
-    response['text']
+    update_transcription(response_text)
+    response_text
   end
 
   def update_transcription(transcribed_text)

lib/chatwoot_markdown_renderer.rb

@@ -5,7 +5,7 @@ class ChatwootMarkdownRenderer
 
   def render_message
     markdown_renderer = BaseMarkdownRenderer.new
-    doc = CommonMarker.render_doc(@content, :DEFAULT)
+    doc = CommonMarker.render_doc(@content, :DEFAULT, [:strikethrough])
     html = markdown_renderer.render(doc)
     render_as_html_safe(html)
   end

lib/integrations/llm_base_service.rb

@@ -1,4 +1,4 @@
-class Integrations::OpenaiBaseService
+class Integrations::LlmBaseService
   include Integrations::LlmInstrumentation
 
   # gpt-4o-mini supports 128,000 tokens
@@ -6,8 +6,7 @@ class Integrations::OpenaiBaseService
   # sticking with 120000 to be safe
   # 120000 * 4 = 480,000 characters (rounding off downwards to 400,000 to be safe)
   TOKEN_LIMIT = 400_000
-  GPT_MODEL = ENV.fetch('OPENAI_GPT_MODEL', 'gpt-4o-mini').freeze
-
+  GPT_MODEL = Llm::Config::DEFAULT_MODEL
   ALLOWED_EVENT_NAMES = %w[rephrase summarize reply_suggestion fix_spelling_grammar shorten expand make_friendly make_formal simplify].freeze
   CACHEABLE_EVENTS = %w[].freeze
 
@@ -82,10 +81,10 @@ class Integrations::OpenaiBaseService
     self.class::CACHEABLE_EVENTS.include?(event_name)
   end
 
-  def api_url
+  def api_base
     endpoint = InstallationConfig.find_by(name: 'CAPTAIN_OPEN_AI_ENDPOINT')&.value.presence || 'https://api.openai.com/'
     endpoint = endpoint.chomp('/')
-    "#{endpoint}/v1/chat/completions"
+    "#{endpoint}/v1"
   end
 
   def make_api_call(body)
@@ -93,10 +92,65 @@ class Integrations::OpenaiBaseService
     instrumentation_params = build_instrumentation_params(parsed_body)
 
     instrument_llm_call(instrumentation_params) do
-      execute_api_request(body, parsed_body['messages'])
+      execute_ruby_llm_request(parsed_body)
     end
   end
 
+  def execute_ruby_llm_request(parsed_body)
+    messages = parsed_body['messages']
+    model = parsed_body['model']
+
+    Llm::Config.with_api_key(hook.settings['api_key'], api_base: api_base) do |context|
+      chat = context.chat(model: model)
+      setup_chat_with_messages(chat, messages)
+    end
+  rescue StandardError => e
+    ChatwootExceptionTracker.new(e, account: hook.account).capture_exception
+    build_error_response_from_exception(e, messages)
+  end
+
+  def setup_chat_with_messages(chat, messages)
+    apply_system_instructions(chat, messages)
+    response = send_conversation_messages(chat, messages)
+    return { error: 'No conversation messages provided', error_code: 400, request_messages: messages } if response.nil?
+
+    build_ruby_llm_response(response, messages)
+  end
+
+  def apply_system_instructions(chat, messages)
+    system_msg = messages.find { |m| m['role'] == 'system' }
+    chat.with_instructions(system_msg['content']) if system_msg
+  end
+
+  def send_conversation_messages(chat, messages)
+    conversation_messages = messages.reject { |m| m['role'] == 'system' }
+
+    return nil if conversation_messages.empty?
+
+    return chat.ask(conversation_messages.first['content']) if conversation_messages.length == 1
+
+    add_conversation_history(chat, conversation_messages[0...-1])
+    chat.ask(conversation_messages.last['content'])
+  end
+
+  def add_conversation_history(chat, messages)
+    messages.each do |msg|
+      chat.add_message(role: msg['role'].to_sym, content: msg['content'])
+    end
+  end
+
+  def build_ruby_llm_response(response, messages)
+    {
+      message: response.content,
+      usage: {
+        'prompt_tokens' => response.input_tokens,
+        'completion_tokens' => response.output_tokens,
+        'total_tokens' => (response.input_tokens || 0) + (response.output_tokens || 0)
+      },
+      request_messages: messages
+    }
+  end
+
   def build_instrumentation_params(parsed_body)
     {
       span_name: "llm.#{event_name}",
@@ -109,37 +163,7 @@ class Integrations::OpenaiBaseService
     }
   end
 
-  def execute_api_request(body, messages)
-    Rails.logger.info("OpenAI API request: #{body}")
-    response = HTTParty.post(api_url, headers: api_headers, body: body)
-    Rails.logger.info("OpenAI API response: #{response.body}")
-
-    parse_api_response(response, messages)
-  end
-
-  def api_headers
-    {
-      'Content-Type' => 'application/json',
-      'Authorization' => "Bearer #{hook.settings['api_key']}"
-    }
-  end
-
-  def parse_api_response(response, messages)
-    return build_error_response(response, messages) unless response.success?
-
-    parsed_response = JSON.parse(response.body)
-    build_success_response(parsed_response, messages)
-  end
-
-  def build_error_response(response, messages)
-    { error: response.parsed_response, error_code: response.code, request_messages: messages }
-  end
-
-  def build_success_response(parsed_response, messages)
-    choices = parsed_response['choices']
-    usage = parsed_response['usage']
-    message_content = choices.present? ? choices.first['message']['content'] : nil
-
-    { message: message_content, usage: usage, request_messages: messages }
+  def build_error_response_from_exception(error, messages)
+    { error: error.message, request_messages: messages }
   end
 end

lib/integrations/llm_instrumentation.rb

@@ -1,45 +1,56 @@
 # frozen_string_literal: true
 
 require 'opentelemetry_config'
-require_relative 'llm_instrumentation_constants'
 
 module Integrations::LlmInstrumentation
   include Integrations::LlmInstrumentationConstants
+  include Integrations::LlmInstrumentationHelpers
+  include Integrations::LlmInstrumentationSpans
 
-  def tracer
-    @tracer ||= OpentelemetryConfig.tracer
-  end
+  PROVIDER_PREFIXES = {
+    'openai' => %w[gpt- o1 o3 o4 text-embedding- whisper- tts-],
+    'anthropic' => %w[claude-],
+    'google' => %w[gemini-],
+    'mistral' => %w[mistral- codestral-],
+    'deepseek' => %w[deepseek-]
+  }.freeze
 
   def instrument_llm_call(params)
     return yield unless ChatwootApp.otel_enabled?
 
+    result = nil
+    executed = false
     tracer.in_span(params[:span_name]) do |span|
       setup_span_attributes(span, params)
       result = yield
+      executed = true
       record_completion(span, result)
       result
     end
   rescue StandardError => e
-    ChatwootExceptionTracker.new(e, account: params[:account]).capture_exception
-    yield
+    ChatwootExceptionTracker.new(e, account: resolve_account(params)).capture_exception
+    executed ? result : yield
   end
 
   def instrument_agent_session(params)
     return yield unless ChatwootApp.otel_enabled?
 
+    result = nil
+    executed = false
     tracer.in_span(params[:span_name]) do |span|
+      set_request_attributes(span, params)
       set_metadata_attributes(span, params)
 
       # By default, the input and output of a trace are set from the root observation
       span.set_attribute(ATTR_LANGFUSE_OBSERVATION_INPUT, params[:messages].to_json)
       result = yield
+      executed = true
       span.set_attribute(ATTR_LANGFUSE_OBSERVATION_OUTPUT, result.to_json)
-
       result
     end
   rescue StandardError => e
-    ChatwootExceptionTracker.new(e, account: params[:account]).capture_exception
-    yield
+    ChatwootExceptionTracker.new(e, account: resolve_account(params)).capture_exception
+    executed ? result : yield
   end
 
   def instrument_tool_call(tool_name, arguments)
@@ -55,8 +66,27 @@ module Integrations::LlmInstrumentation
     end
   end
 
+  def determine_provider(model_name)
+    return 'openai' if model_name.blank?
+
+    model = model_name.to_s.downcase
+
+    PROVIDER_PREFIXES.each do |provider, prefixes|
+      return provider if prefixes.any? { |prefix| model.start_with?(prefix) }
+    end
+
+    'openai'
+  end
+
   private
 
+  def resolve_account(params)
+    return params[:account] if params[:account].is_a?(Account)
+    return Account.find_by(id: params[:account_id]) if params[:account_id].present?
+
+    nil
+  end
+
   def setup_span_attributes(span, params)
     set_request_attributes(span, params)
     set_prompt_messages(span, params[:messages])
@@ -64,11 +94,17 @@ module Integrations::LlmInstrumentation
   end
 
   def record_completion(span, result)
-    set_completion_attributes(span, result) if result.is_a?(Hash)
+    if result.respond_to?(:content)
+      span.set_attribute(ATTR_GEN_AI_COMPLETION_ROLE, result.role.to_s) if result.respond_to?(:role)
+      span.set_attribute(ATTR_GEN_AI_COMPLETION_CONTENT, result.content.to_s)
+    elsif result.is_a?(Hash)
+      set_completion_attributes(span, result) if result.is_a?(Hash)
+    end
   end
 
   def set_request_attributes(span, params)
-    span.set_attribute(ATTR_GEN_AI_PROVIDER, 'openai')
+    provider = determine_provider(params[:model])
+    span.set_attribute(ATTR_GEN_AI_PROVIDER, provider)
     span.set_attribute(ATTR_GEN_AI_REQUEST_MODEL, params[:model])
     span.set_attribute(ATTR_GEN_AI_REQUEST_TEMPERATURE, params[:temperature]) if params[:temperature]
   end
@@ -82,50 +118,4 @@ module Integrations::LlmInstrumentation
       span.set_attribute(format(ATTR_GEN_AI_PROMPT_CONTENT, idx), content.to_s)
     end
   end
-
-  def set_metadata_attributes(span, params)
-    session_id = params[:conversation_id].present? ? "#{params[:account_id]}_#{params[:conversation_id]}" : nil
-    span.set_attribute(ATTR_LANGFUSE_USER_ID, params[:account_id].to_s) if params[:account_id]
-    span.set_attribute(ATTR_LANGFUSE_SESSION_ID, session_id) if session_id.present?
-    span.set_attribute(ATTR_LANGFUSE_TAGS, [params[:feature_name]].to_json)
-
-    return unless params[:metadata].is_a?(Hash)
-
-    params[:metadata].each do |key, value|
-      span.set_attribute(format(ATTR_LANGFUSE_METADATA, key), value.to_s)
-    end
-  end
-
-  def set_completion_attributes(span, result)
-    set_completion_message(span, result)
-    set_usage_metrics(span, result)
-    set_error_attributes(span, result)
-  end
-
-  def set_completion_message(span, result)
-    message = result[:message] || result.dig('choices', 0, 'message', 'content')
-    return if message.blank?
-
-    span.set_attribute(ATTR_GEN_AI_COMPLETION_ROLE, 'assistant')
-    span.set_attribute(ATTR_GEN_AI_COMPLETION_CONTENT, message)
-  end
-
-  def set_usage_metrics(span, result)
-    usage = result[:usage] || result['usage']
-    return if usage.blank?
-
-    span.set_attribute(ATTR_GEN_AI_USAGE_INPUT_TOKENS, usage['prompt_tokens']) if usage['prompt_tokens']
-    span.set_attribute(ATTR_GEN_AI_USAGE_OUTPUT_TOKENS, usage['completion_tokens']) if usage['completion_tokens']
-    span.set_attribute(ATTR_GEN_AI_USAGE_TOTAL_TOKENS, usage['total_tokens']) if usage['total_tokens']
-  end
-
-  def set_error_attributes(span, result)
-    error = result[:error] || result['error']
-    return if error.blank?
-
-    error_code = result[:error_code] || result['error_code']
-    span.set_attribute(ATTR_GEN_AI_RESPONSE_ERROR, error.to_json)
-    span.set_attribute(ATTR_GEN_AI_RESPONSE_ERROR_CODE, error_code) if error_code
-    span.status = OpenTelemetry::Trace::Status.error("API Error: #{error_code}")
-  end
 end

lib/integrations/llm_instrumentation_helpers.rb

@@ -0,0 +1,51 @@
+# frozen_string_literal: true
+
+module Integrations::LlmInstrumentationHelpers
+  include Integrations::LlmInstrumentationConstants
+
+  private
+
+  def set_completion_attributes(span, result)
+    set_completion_message(span, result)
+    set_usage_metrics(span, result)
+    set_error_attributes(span, result)
+  end
+
+  def set_completion_message(span, result)
+    message = result[:message] || result.dig('choices', 0, 'message', 'content')
+    return if message.blank?
+
+    span.set_attribute(ATTR_GEN_AI_COMPLETION_ROLE, 'assistant')
+    span.set_attribute(ATTR_GEN_AI_COMPLETION_CONTENT, message)
+  end
+
+  def set_usage_metrics(span, result)
+    usage = result[:usage] || result['usage']
+    return if usage.blank?
+
+    span.set_attribute(ATTR_GEN_AI_USAGE_INPUT_TOKENS, usage['prompt_tokens']) if usage['prompt_tokens']
+    span.set_attribute(ATTR_GEN_AI_USAGE_OUTPUT_TOKENS, usage['completion_tokens']) if usage['completion_tokens']
+    span.set_attribute(ATTR_GEN_AI_USAGE_TOTAL_TOKENS, usage['total_tokens']) if usage['total_tokens']
+  end
+
+  def set_error_attributes(span, result)
+    error = result[:error] || result['error']
+    return if error.blank?
+
+    span.set_attribute(ATTR_GEN_AI_RESPONSE_ERROR, error.to_json)
+    span.status = OpenTelemetry::Trace::Status.error(error.to_s.truncate(1000))
+  end
+
+  def set_metadata_attributes(span, params)
+    session_id = params[:conversation_id].present? ? "#{params[:account_id]}_#{params[:conversation_id]}" : nil
+    span.set_attribute(ATTR_LANGFUSE_USER_ID, params[:account_id].to_s) if params[:account_id]
+    span.set_attribute(ATTR_LANGFUSE_SESSION_ID, session_id) if session_id.present?
+    span.set_attribute(ATTR_LANGFUSE_TAGS, [params[:feature_name]].to_json)
+
+    return unless params[:metadata].is_a?(Hash)
+
+    params[:metadata].each do |key, value|
+      span.set_attribute(format(ATTR_LANGFUSE_METADATA, key), value.to_s)
+    end
+  end
+end

lib/integrations/llm_instrumentation_spans.rb

@@ -0,0 +1,92 @@
+# frozen_string_literal: true
+
+require 'opentelemetry_config'
+require_relative 'llm_instrumentation_constants'
+
+module Integrations::LlmInstrumentationSpans
+  include Integrations::LlmInstrumentationConstants
+
+  def tracer
+    @tracer ||= OpentelemetryConfig.tracer
+  end
+
+  def start_llm_turn_span(params)
+    return unless ChatwootApp.otel_enabled?
+
+    span = tracer.start_span(params[:span_name])
+    set_llm_turn_request_attributes(span, params)
+    set_llm_turn_prompt_attributes(span, params[:messages]) if params[:messages]
+
+    @pending_llm_turn_spans ||= []
+    @pending_llm_turn_spans.push(span)
+  rescue StandardError => e
+    Rails.logger.warn "Failed to start LLM turn span: #{e.message}"
+  end
+
+  def end_llm_turn_span(message)
+    return unless ChatwootApp.otel_enabled?
+
+    span = @pending_llm_turn_spans&.pop
+    return unless span
+
+    set_llm_turn_response_attributes(span, message) if message
+    span.finish
+  rescue StandardError => e
+    Rails.logger.warn "Failed to end LLM turn span: #{e.message}"
+  end
+
+  def start_tool_span(tool_call)
+    return unless ChatwootApp.otel_enabled?
+
+    tool_name = tool_call.name.to_s
+    span = tracer.start_span(format(TOOL_SPAN_NAME, tool_name))
+    span.set_attribute(ATTR_LANGFUSE_OBSERVATION_INPUT, tool_call.arguments.to_json)
+
+    @pending_tool_spans ||= []
+    @pending_tool_spans.push(span)
+  rescue StandardError => e
+    Rails.logger.warn "Failed to start tool span: #{e.message}"
+  end
+
+  def end_tool_span(result)
+    return unless ChatwootApp.otel_enabled?
+
+    span = @pending_tool_spans&.pop
+    return unless span
+
+    output = result.is_a?(String) ? result : result.to_json
+    span.set_attribute(ATTR_LANGFUSE_OBSERVATION_OUTPUT, output)
+    span.finish
+  rescue StandardError => e
+    Rails.logger.warn "Failed to end tool span: #{e.message}"
+  end
+
+  private
+
+  def set_llm_turn_request_attributes(span, params)
+    provider = determine_provider(params[:model])
+    span.set_attribute(ATTR_GEN_AI_PROVIDER, provider)
+    span.set_attribute(ATTR_GEN_AI_REQUEST_MODEL, params[:model]) if params[:model]
+    span.set_attribute(ATTR_GEN_AI_REQUEST_TEMPERATURE, params[:temperature]) if params[:temperature]
+  end
+
+  def set_llm_turn_prompt_attributes(span, messages)
+    messages.each_with_index do |msg, idx|
+      span.set_attribute(format(ATTR_GEN_AI_PROMPT_ROLE, idx), msg[:role])
+      span.set_attribute(format(ATTR_GEN_AI_PROMPT_CONTENT, idx), msg[:content])
+    end
+    span.set_attribute(ATTR_LANGFUSE_OBSERVATION_INPUT, messages.to_json)
+  end
+
+  def set_llm_turn_response_attributes(span, message)
+    span.set_attribute(ATTR_GEN_AI_COMPLETION_ROLE, message.role.to_s) if message.respond_to?(:role)
+    span.set_attribute(ATTR_GEN_AI_COMPLETION_CONTENT, message.content.to_s) if message.respond_to?(:content)
+    set_llm_turn_usage_attributes(span, message)
+    span.set_attribute(ATTR_LANGFUSE_OBSERVATION_OUTPUT, message.content.to_s) if message.respond_to?(:content)
+  end
+
+  def set_llm_turn_usage_attributes(span, message)
+    span.set_attribute(ATTR_GEN_AI_USAGE_INPUT_TOKENS, message.input_tokens) if message.respond_to?(:input_tokens) && message.input_tokens
+    span.set_attribute(ATTR_GEN_AI_USAGE_OUTPUT_TOKENS, message.output_tokens) if message.respond_to?(:output_tokens) && message.output_tokens
+  end
+end

lib/integrations/openai/processor_service.rb

@@ -1,4 +1,4 @@
-class Integrations::Openai::ProcessorService < Integrations::OpenaiBaseService
+class Integrations::Openai::ProcessorService < Integrations::LlmBaseService
   AGENT_INSTRUCTION = 'You are a helpful support agent.'.freeze
   LANGUAGE_INSTRUCTION = 'Ensure that the reply should be in user language.'.freeze
   def reply_suggestion_message

lib/integrations/slack/send_on_slack_service.rb

@@ -121,8 +121,6 @@ class Integrations::Slack::SendOnSlackService < Base::SendOnChannelService
   end
 
   def upload_files
-    return unless message.attachments.any?
-
     files = build_files_array
     return if files.empty?
 
@@ -136,6 +134,8 @@ class Integrations::Slack::SendOnSlackService < Base::SendOnChannelService
       Rails.logger.info "slack_upload_result: #{result}"
     rescue Slack::Web::Api::Errors::SlackError => e
       Rails.logger.error "Failed to upload files: #{e.message}"
+    ensure
+      files.each { |file| file[:content]&.clear }
     end
   end
 
@@ -143,14 +143,31 @@ class Integrations::Slack::SendOnSlackService < Base::SendOnChannelService
     message.attachments.filter_map do |attachment|
       next unless attachment.with_attached_file?
 
-      {
-        filename: attachment.file.filename.to_s,
-        content: attachment.file.download,
-        title: attachment.file.filename.to_s
-      }
+      build_file_payload(attachment)
     end
   end
 
+  def build_file_payload(attachment)
+    content = download_attachment_content(attachment)
+    return if content.blank?
+
+    {
+      filename: attachment.file.filename.to_s,
+      content: content,
+      title: attachment.file.filename.to_s
+    }
+  end
+
+  def download_attachment_content(attachment)
+    buffer = +''
+    attachment.file.blob.open do |file|
+      while (chunk = file.read(64.kilobytes))
+        buffer << chunk
+      end
+    end
+    buffer
+  end
+
   def sender_name(sender)
     sender.try(:name) ? "#{sender.try(:name)} (#{sender_type(sender)})" : sender_type(sender)
   end

lib/llm/config.rb

@@ -0,0 +1,48 @@
+require 'ruby_llm'
+
+module Llm::Config
+  DEFAULT_MODEL = 'gpt-4o-mini'.freeze
+  class << self
+    def initialized?
+      @initialized ||= false
+    end
+
+    def initialize!
+      return if @initialized
+
+      configure_ruby_llm
+      @initialized = true
+    end
+
+    def reset!
+      @initialized = false
+    end
+
+    def with_api_key(api_key, api_base: nil)
+      context = RubyLLM.context do |config|
+        config.openai_api_key = api_key
+        config.openai_api_base = api_base
+      end
+
+      yield context
+    end
+
+    private
+
+    def configure_ruby_llm
+      RubyLLM.configure do |config|
+        config.openai_api_key = system_api_key if system_api_key.present?
+        config.openai_api_base = openai_endpoint.chomp('/') if openai_endpoint.present?
+        config.logger = Rails.logger
+      end
+    end
+
+    def system_api_key
+      InstallationConfig.find_by(name: 'CAPTAIN_OPEN_AI_API_KEY')&.value
+    end
+
+    def openai_endpoint
+      InstallationConfig.find_by(name: 'CAPTAIN_OPEN_AI_ENDPOINT')&.value
+    end
+  end
+end

lib/tasks/auto_annotate_models.rake

@@ -2,11 +2,14 @@
 # NOTE: are sensitive to local FS writes, and besides -- it's just not proper
 # NOTE: to have a dev-mode tool do its thing in production.
 if Rails.env.development?
-  require 'annotate'
+  require 'annotate_rb'
+
+  AnnotateRb::Core.load_rake_tasks
+
   task :set_annotation_options do
     # You can override any of these by setting an environment variable of the
     # same name.
-    Annotate.set_defaults(
+    AnnotateRb::Options.set_defaults(
       'additional_file_patterns' => [],
       'routes' => 'false',
       'models' => 'true',
@@ -55,6 +58,4 @@ if Rails.env.development?
       'with_comment' => 'true'
     )
   end
-
-  Annotate.load_tasks
 end

package.json

@@ -37,7 +37,7 @@
   "dependencies": {
     "@breezystack/lamejs": "^1.2.7",
     "@chatwoot/ninja-keys": "1.2.3",
-    "@chatwoot/prosemirror-schema": "1.2.3",
+    "@chatwoot/prosemirror-schema": "1.2.6",
     "@chatwoot/utils": "^0.0.51",
     "@formkit/core": "^1.6.7",
     "@formkit/vue": "^1.6.7",
@@ -49,7 +49,7 @@
     "@rails/actioncable": "6.1.3",
     "@rails/ujs": "^7.1.400",
     "@scmmishra/pico-search": "0.5.4",
-    "@sentry/vue": "^8.31.0",
+    "@sentry/vue": "^8.55.0",
     "@sindresorhus/slugify": "2.2.1",
     "@tailwindcss/typography": "^0.5.15",
     "@tanstack/vue-table": "^8.20.5",
@@ -60,7 +60,7 @@
     "@vueuse/components": "^12.0.0",
     "@vueuse/core": "^12.0.0",
     "activestorage": "^5.2.6",
-    "axios": "^1.8.2",
+    "axios": "^1.13.2",
     "camelcase-keys": "^9.1.3",
     "chart.js": "~4.4.4",
     "color2k": "^2.0.2",
@@ -137,8 +137,8 @@
     "fake-indexeddb": "^6.0.0",
     "histoire": "0.17.15",
     "husky": "^7.0.0",
-    "jsdom": "^24.1.3",
-    "lint-staged": "14.0.1",
+    "jsdom": "^27.2.0",
+    "lint-staged": "^16.2.7",
     "postcss": "^8.4.47",
     "postcss-preset-env": "^8.5.1",
     "prettier": "^3.3.3",

rubocop/attachment_download.rb

@@ -0,0 +1,17 @@
+require 'rubocop'
+
+module RuboCop::Cop::Chatwoot; end
+
+class RuboCop::Cop::Chatwoot::AttachmentDownload < RuboCop::Cop::Base
+  MSG = 'Avoid calling `.file/.blob.download`; use `blob.open` or streaming IO instead.'.freeze
+
+  def_node_matcher :unsafe_download?, <<~PATTERN
+    (send (send _ {:file :blob}) :download ...)
+  PATTERN
+
+  def on_send(node)
+    return unless unsafe_download?(node)
+
+    add_offense(node.loc.selector, message: MSG)
+  end
+end

spec/enterprise/controllers/enterprise/api/v1/accounts_controller_spec.rb

@@ -245,6 +245,78 @@ RSpec.describe 'Enterprise Billing APIs', type: :request do
     end
   end
 
+  describe 'POST /enterprise/api/v1/accounts/{account.id}/topup_checkout' do
+    let(:stripe_customer_id) { 'cus_test123' }
+    let(:invoice_settings) { Struct.new(:default_payment_method).new('pm_test123') }
+    let(:stripe_customer) { Struct.new(:invoice_settings, :default_source).new(invoice_settings, nil) }
+    let(:stripe_invoice) { Struct.new(:id).new('inv_test123') }
+
+    before do
+      create(:installation_config, name: 'CHATWOOT_CLOUD_PLANS', value: [
+               { 'name' => 'Hacker', 'product_id' => ['prod_hacker'], 'price_ids' => ['price_hacker'] },
+               { 'name' => 'Business', 'product_id' => ['prod_business'], 'price_ids' => ['price_business'] }
+             ])
+    end
+
+    it 'returns unauthorized for unauthenticated user' do
+      post "/enterprise/api/v1/accounts/#{account.id}/topup_checkout", as: :json
+      expect(response).to have_http_status(:unauthorized)
+    end
+
+    it 'returns unauthorized for agent' do
+      post "/enterprise/api/v1/accounts/#{account.id}/topup_checkout",
+           headers: agent.create_new_auth_token,
+           params: { credits: 1000 },
+           as: :json
+      expect(response).to have_http_status(:unauthorized)
+    end
+
+    context 'when it is an admin' do
+      before do
+        account.update!(
+          custom_attributes: { plan_name: 'Business', stripe_customer_id: stripe_customer_id },
+          limits: { 'captain_responses' => 1000 }
+        )
+        allow(Stripe::Customer).to receive(:retrieve).with(stripe_customer_id).and_return(stripe_customer)
+        allow(Stripe::Invoice).to receive(:create).and_return(stripe_invoice)
+        allow(Stripe::InvoiceItem).to receive(:create)
+        allow(Stripe::Invoice).to receive(:finalize_invoice)
+        allow(Stripe::Invoice).to receive(:pay)
+        allow(Stripe::Billing::CreditGrant).to receive(:create)
+      end
+
+      it 'successfully processes topup and returns correct response' do
+        post "/enterprise/api/v1/accounts/#{account.id}/topup_checkout",
+             headers: admin.create_new_auth_token,
+             params: { credits: 1000 },
+             as: :json
+
+        expect(response).to have_http_status(:success)
+        json_response = JSON.parse(response.body)
+        expect(json_response['credits']).to eq(1000)
+        expect(json_response['amount']).to eq(20.0)
+        expect(json_response['limits']['captain_responses']).to eq(2000)
+      end
+
+      it 'returns error when credits parameter is missing' do
+        post "/enterprise/api/v1/accounts/#{account.id}/topup_checkout",
+             headers: admin.create_new_auth_token,
+             as: :json
+
+        expect(response).to have_http_status(:unprocessable_entity)
+      end
+
+      it 'returns error for invalid credits amount' do
+        post "/enterprise/api/v1/accounts/#{account.id}/topup_checkout",
+             headers: admin.create_new_auth_token,
+             params: { credits: 999 },
+             as: :json
+
+        expect(response).to have_http_status(:unprocessable_entity)
+      end
+    end
+  end
+
   describe 'POST /enterprise/api/v1/accounts/{account.id}/toggle_deletion' do
     context 'when it is an unauthenticated user' do
       it 'returns unauthorized' do

spec/enterprise/lib/integrations/openai/processor_service_spec.rb

@@ -5,21 +5,39 @@ RSpec.describe Integrations::Openai::ProcessorService do
 
   let(:account) { create(:account) }
   let(:hook) { create(:integrations_hook, :openai, account: account) }
-  let(:expected_headers) { { 'Authorization' => "Bearer #{hook.settings['api_key']}" } }
-  let(:openai_response) do
-    {
-      'choices' => [
-        {
-          'message' => {
-            'content' => 'This is a reply from openai.'
-          }
-        }
-      ]
-    }.to_json
+
+  # Mock RubyLLM objects
+  let(:mock_chat) { instance_double(RubyLLM::Chat) }
+  let(:mock_context) { instance_double(RubyLLM::Context) }
+  let(:mock_config) { OpenStruct.new }
+  let(:mock_response) do
+    instance_double(
+      RubyLLM::Message,
+      content: 'This is a reply from openai.',
+      input_tokens: nil,
+      output_tokens: nil
+    )
+  end
+  let(:mock_empty_response) do
+    instance_double(
+      RubyLLM::Message,
+      content: '',
+      input_tokens: nil,
+      output_tokens: nil
+    )
   end
 
   let(:conversation) { create(:conversation, account: account) }
 
+  before do
+    allow(RubyLLM).to receive(:context).and_yield(mock_config).and_return(mock_context)
+    allow(mock_context).to receive(:chat).and_return(mock_chat)
+
+    allow(mock_chat).to receive(:with_instructions).and_return(mock_chat)
+    allow(mock_chat).to receive(:add_message).and_return(mock_chat)
+    allow(mock_chat).to receive(:ask).and_return(mock_response)
+  end
+
   describe '#perform' do
     context 'when event name is label_suggestion with labels with < 3 messages' do
       let(:event) { { 'name' => 'label_suggestion', 'data' => { 'conversation_display_id' => conversation.display_id } } }
@@ -49,21 +67,15 @@ RSpec.describe Integrations::Openai::ProcessorService do
       end
 
       it 'returns the label suggestions' do
-        stub_request(:post, 'https://api.openai.com/v1/chat/completions')
-          .with(body: anything, headers: expected_headers)
-          .to_return(status: 200, body: openai_response, headers: {})
-
         result = subject.perform
-        expect(result).to eq({ :message => 'This is a reply from openai.' })
+        expect(result).to eq({ message: 'This is a reply from openai.' })
       end
 
       it 'returns empty string if openai response is blank' do
-        stub_request(:post, 'https://api.openai.com/v1/chat/completions')
-          .with(body: anything, headers: expected_headers)
-          .to_return(status: 200, body: '{}', headers: {})
+        allow(mock_chat).to receive(:ask).and_return(mock_empty_response)
 
         result = subject.perform
-        expect(result).to eq({ :message => '' })
+        expect(result[:message]).to eq('')
       end
     end
 

spec/enterprise/services/captain/copilot/chat_service_spec.rb

@@ -7,7 +7,6 @@ RSpec.describe Captain::Copilot::ChatService do
   let(:assistant) { create(:captain_assistant, account: account) }
   let(:contact) { create(:contact, account: account) }
   let(:conversation) { create(:conversation, account: account, inbox: inbox, contact: contact) }
-  let(:mock_openai_client) { instance_double(OpenAI::Client) }
   let(:copilot_thread) { create(:captain_copilot_thread, account: account, user: user) }
   let!(:copilot_message) do
     create(
@@ -20,13 +19,29 @@ RSpec.describe Captain::Copilot::ChatService do
     { user_id: user.id, copilot_thread_id: copilot_thread.id, conversation_id: conversation.display_id }
   end
 
+  # RubyLLM mocks
+  let(:mock_chat) { instance_double(RubyLLM::Chat) }
+  let(:mock_response) do
+    instance_double(RubyLLM::Message, content: '{ "content": "Hey", "reasoning": "Test reasoning", "reply_suggestion": false }')
+  end
+
   before do
-    create(:installation_config, name: 'CAPTAIN_OPEN_AI_API_KEY', value: 'test-key')
-    create(:installation_config, name: 'CAPTAIN_OPEN_AI_ENDPOINT', value: 'https://api.openai.com/')
-    allow(OpenAI::Client).to receive(:new).and_return(mock_openai_client)
-    allow(mock_openai_client).to receive(:chat).and_return({
-      choices: [{ message: { content: '{ "content": "Hey" }' } }]
-    }.with_indifferent_access)
+    InstallationConfig.find_or_create_by(name: 'CAPTAIN_OPEN_AI_API_KEY') do |c|
+      c.value = 'test-key'
+    end
+
+    allow(RubyLLM).to receive(:chat).and_return(mock_chat)
+    allow(mock_chat).to receive(:with_temperature).and_return(mock_chat)
+    allow(mock_chat).to receive(:with_params).and_return(mock_chat)
+    allow(mock_chat).to receive(:with_tool).and_return(mock_chat)
+    allow(mock_chat).to receive(:with_instructions).and_return(mock_chat)
+    allow(mock_chat).to receive(:add_message).and_return(mock_chat)
+    allow(mock_chat).to receive(:on_new_message).and_return(mock_chat)
+    allow(mock_chat).to receive(:on_end_message).and_return(mock_chat)
+    allow(mock_chat).to receive(:on_tool_call).and_return(mock_chat)
+    allow(mock_chat).to receive(:on_tool_result).and_return(mock_chat)
+    allow(mock_chat).to receive(:messages).and_return([])
+    allow(mock_chat).to receive(:ask).and_return(mock_response)
   end
 
   describe '#initialize' do
@@ -48,48 +63,6 @@ RSpec.describe Captain::Copilot::ChatService do
       expect(messages.second[:role]).to eq('system')
       expect(messages.second[:content]).to include(account.id.to_s)
     end
-
-    it 'initializes OpenAI client with configured endpoint' do
-      expect(OpenAI::Client).to receive(:new).with(
-        access_token: 'test-key',
-        uri_base: 'https://api.openai.com/',
-        log_errors: Rails.env.development?
-      )
-
-      described_class.new(assistant, config)
-    end
-
-    context 'when CAPTAIN_OPEN_AI_ENDPOINT is not configured' do
-      before do
-        InstallationConfig.find_by(name: 'CAPTAIN_OPEN_AI_ENDPOINT')&.destroy
-      end
-
-      it 'uses default OpenAI endpoint' do
-        expect(OpenAI::Client).to receive(:new).with(
-          access_token: 'test-key',
-          uri_base: 'https://api.openai.com/',
-          log_errors: Rails.env.development?
-        )
-
-        described_class.new(assistant, config)
-      end
-    end
-
-    context 'when custom endpoint is configured' do
-      before do
-        InstallationConfig.find_by(name: 'CAPTAIN_OPEN_AI_ENDPOINT').update!(value: 'https://custom.azure.com/')
-      end
-
-      it 'uses custom endpoint for OpenAI client' do
-        expect(OpenAI::Client).to receive(:new).with(
-          access_token: 'test-key',
-          uri_base: 'https://custom.azure.com/',
-          log_errors: Rails.env.development?
-        )
-
-        described_class.new(assistant, config)
-      end
-    end
   end
 
   describe '#generate_response' do
@@ -112,82 +85,19 @@ RSpec.describe Captain::Copilot::ChatService do
     end
 
     it 'returns the response from request_chat_completion' do
-      expect(service.generate_response('Hello')).to eq({ 'content' => 'Hey' })
+      result = service.generate_response('Hello')
+
+      expect(result).to eq({ 'content' => 'Hey', 'reasoning' => 'Test reasoning', 'reply_suggestion' => false })
     end
 
-    context 'when response contains tool calls' do
-      before do
-        allow(mock_openai_client).to receive(:chat).and_return(
-          {
-            choices: [{ message: { 'tool_calls' => tool_calls } }]
-          }.with_indifferent_access,
-          {
-            choices: [{ message: { content: '{ "content": "Tool response processed" }' } }]
-          }.with_indifferent_access
-        )
-      end
-
-      context 'when tool call is valid' do
-        let(:tool_calls) do
-          [{
-            'id' => 'call_123',
-            'function' => {
-              'name' => 'get_conversation',
-              'arguments' => "{ \"conversation_id\": #{conversation.display_id} }"
-            }
-          }]
-        end
-
-        it 'processes tool calls and appends them to messages' do
-          result = service.generate_response("Find conversation #{conversation.id}")
-
-          expect(result).to eq({ 'content' => 'Tool response processed' })
-          expect(service.messages).to include(
-            { role: 'assistant', tool_calls: tool_calls }
-          )
-          expect(service.messages).to include(
-            {
-              role: 'tool', tool_call_id: 'call_123', content: conversation.to_llm_text
-            }
-          )
-
-          expect(result).to eq({ 'content' => 'Tool response processed' })
-        end
-      end
-
-      context 'when tool call is invalid' do
-        let(:tool_calls) do
-          [{
-            'id' => 'call_123',
-            'function' => {
-              'name' => 'get_settings',
-              'arguments' => '{}'
-            }
-          }]
-        end
-
-        it 'handles invalid tool calls' do
-          result = service.generate_response('Find settings')
-
-          expect(result).to eq({ 'content' => 'Tool response processed' })
-          expect(service.messages).to include(
-            {
-              role: 'assistant', tool_calls: tool_calls
-            }
-          )
-          expect(service.messages).to include(
-            {
-              role: 'tool',
-              tool_call_id: 'call_123',
-              content: 'Tool not available'
-            }
-          )
-        end
-      end
+    it 'increments response usage for the account' do
+      expect do
+        service.generate_response('Hello')
+      end.to(change { account.reload.custom_attributes['captain_responses_usage'].to_i }.by(1))
     end
   end
 
-  describe '#setup_user' do
+  describe 'user setup behavior' do
     it 'sets user when user_id is present in config' do
       service = described_class.new(assistant, { user_id: user.id })
       expect(service.user).to eq(user)
@@ -199,7 +109,7 @@ RSpec.describe Captain::Copilot::ChatService do
     end
   end
 
-  describe '#setup_message_history' do
+  describe 'message history behavior' do
     context 'when copilot_thread_id is present' do
       it 'finds the copilot thread and sets previous history from it' do
         service = described_class.new(assistant, { copilot_thread_id: copilot_thread.id })
@@ -227,7 +137,7 @@ RSpec.describe Captain::Copilot::ChatService do
     end
   end
 
-  describe '#build_messages' do
+  describe 'message building behavior' do
     it 'includes system message and account context' do
       service = described_class.new(assistant, {})
       messages = service.messages
@@ -257,13 +167,9 @@ RSpec.describe Captain::Copilot::ChatService do
     end
   end
 
-  describe '#persist_message' do
+  describe 'message persistence behavior' do
     context 'when copilot_thread is present' do
-      it 'creates a copilot message' do
-        allow(mock_openai_client).to receive(:chat).and_return({
-          choices: [{ message: { content: '{ "content": "Hey" }' } }]
-        }.with_indifferent_access)
-
+      it 'creates a copilot message with the response' do
         expect do
           described_class.new(assistant, { copilot_thread_id: copilot_thread.id }).generate_response('Hello')
         end.to change(CopilotMessage, :count).by(1)
@@ -276,10 +182,6 @@ RSpec.describe Captain::Copilot::ChatService do
 
     context 'when copilot_thread is not present' do
       it 'does not create a copilot message' do
-        allow(mock_openai_client).to receive(:chat).and_return({
-          choices: [{ message: { content: '{ "content": "Hey" }' } }]
-        }.with_indifferent_access)
-
         expect do
           described_class.new(assistant, {}).generate_response('Hello')
         end.not_to(change(CopilotMessage, :count))

spec/enterprise/services/captain/llm/pdf_processing_service_spec.rb

@@ -28,13 +28,14 @@ RSpec.describe Captain::Llm::PdfProcessingService do
     context 'when uploading PDF to OpenAI' do
       let(:mock_client) { instance_double(OpenAI::Client) }
       let(:pdf_content) { 'PDF content' }
+      let(:blob_double) { instance_double(ActiveStorage::Blob) }
+      let(:pdf_file) { instance_double(ActiveStorage::Attachment) }
 
       before do
         allow(document).to receive(:openai_file_id).and_return(nil)
-
-        # Use a simple double for ActiveStorage since it's a complex Rails object
-        pdf_file = double('pdf_file', download: pdf_content) # rubocop:disable RSpec/VerifiedDoubles
         allow(document).to receive(:pdf_file).and_return(pdf_file)
+        allow(pdf_file).to receive(:blob).and_return(blob_double)
+        allow(blob_double).to receive(:open).and_yield(StringIO.new(pdf_content))
 
         allow(OpenAI::Client).to receive(:new).and_return(mock_client)
         # Use a simple double for OpenAI::Files as it may not be loaded

spec/enterprise/services/captain/tools/copilot/get_article_service_spec.rb

@@ -19,19 +19,8 @@ RSpec.describe Captain::Tools::Copilot::GetArticleService do
   end
 
   describe '#parameters' do
-    it 'returns the expected parameter schema' do
-      expect(service.parameters).to eq(
-        {
-          type: 'object',
-          properties: {
-            article_id: {
-              type: 'number',
-              description: 'The ID of the article to retrieve'
-            }
-          },
-          required: %w[article_id]
-        }
-      )
+    it 'defines article_id parameter' do
+      expect(service.parameters.keys).to contain_exactly(:article_id)
     end
   end
 
@@ -79,13 +68,13 @@ RSpec.describe Captain::Tools::Copilot::GetArticleService do
   describe '#execute' do
     context 'when article_id is blank' do
       it 'returns error message' do
-        expect(service.execute({})).to eq('Missing required parameters')
+        expect(service.execute(article_id: nil)).to eq('Article not found')
       end
     end
 
     context 'when article is not found' do
       it 'returns not found message' do
-        expect(service.execute({ 'article_id' => 999 })).to eq('Article not found')
+        expect(service.execute(article_id: 999)).to eq('Article not found')
       end
     end
 
@@ -94,7 +83,7 @@ RSpec.describe Captain::Tools::Copilot::GetArticleService do
       let(:article) { create(:article, account: account, portal: portal, author: user, title: 'Test Article', content: 'Content') }
 
       it 'returns the article in llm text format' do
-        result = service.execute({ 'article_id' => article.id })
+        result = service.execute(article_id: article.id)
         expect(result).to eq(article.to_llm_text)
       end
 
@@ -104,7 +93,7 @@ RSpec.describe Captain::Tools::Copilot::GetArticleService do
         let(:other_article) { create(:article, account: other_account, portal: other_portal, author: user, title: 'Other Article') }
 
         it 'returns not found message' do
-          expect(service.execute({ 'article_id' => other_article.id })).to eq('Article not found')
+          expect(service.execute(article_id: other_article.id)).to eq('Article not found')
         end
       end
     end