diff --git a/AGENTS.md b/AGENTS.md
index 3b1bcb024..301633d7f 100644
--- a/AGENTS.md
+++ b/AGENTS.md
@@ -4,6 +4,11 @@
 
 - **Setup**: `bundle install && pnpm install`
 - **Run Dev**: `pnpm dev` or `overmind start -f ./Procfile.dev`
+- **Seed Local Test Data**: `bundle exec rails db:seed` (quickly populates minimal data for standard feature verification)
+- **Seed Search Test Data**: `bundle exec rails search:setup_test_data` (bulk fixture generation for search/performance/manual load scenarios)
+- **Seed Account Sample Data (richer test data)**: `Seeders::AccountSeeder` is available as an internal utility and is exposed through Super Admin `Accounts#seed`, but can be used directly in dev workflows too:
+  - UI path: Super Admin → Accounts → Seed (enqueues `Internal::SeedAccountJob`).
+  - CLI path: `bundle exec rails runner "Internal::SeedAccountJob.perform_now(Account.find(<id>))"` (or call `Seeders::AccountSeeder.new(account: Account.find(<id>)).perform!` directly).
 - **Lint JS/Vue**: `pnpm eslint` / `pnpm eslint:fix`
 - **Lint Ruby**: `bundle exec rubocop -a`
 - **Test JS**: `pnpm test` or `pnpm test:watch`
@@ -93,3 +98,7 @@ Practical checklist for any change impacting core logic or public APIs
 - When renaming/moving shared code, mirror the change in `enterprise/` to prevent drift.
 - Tests: Add Enterprise-specific specs under `spec/enterprise`, mirroring OSS spec layout where applicable.
 - When modifying existing OSS features for Enterprise-only behavior, add an Enterprise module (via `prepend_mod_with`/`include_mod_with`) instead of editing OSS files directly—especially for policies, controllers, and services. For Enterprise-exclusive features, place code directly under `enterprise/`.
+
+## Branding / White-labeling note
+
+- For user-facing strings that currently contain "Chatwoot" but should adapt to branded/self-hosted installs, prefer applying `replaceInstallationName` from `shared/composables/useBranding` in the UI layer (for example tooltip and suggestion labels) instead of adding hardcoded brand-specific copy.
diff --git a/Gemfile b/Gemfile
index 2023c32b1..e6c5a5250 100644
--- a/Gemfile
+++ b/Gemfile
@@ -191,7 +191,7 @@ gem 'reverse_markdown'
 
 gem 'iso-639'
 gem 'ruby-openai'
-gem 'ai-agents', '>= 0.7.0'
+gem 'ai-agents'
 
 # TODO: Move this gem as a dependency of ai-agents
 gem 'ruby_llm', '>= 1.8.2'
diff --git a/Gemfile.lock b/Gemfile.lock
index db9b59c66..cc1f9e253 100644
--- a/Gemfile.lock
+++ b/Gemfile.lock
@@ -126,8 +126,8 @@ GEM
       jbuilder (~> 2)
       rails (>= 4.2, < 7.2)
       selectize-rails (~> 0.6)
-    ai-agents (0.7.0)
-      ruby_llm (~> 1.8.2)
+    ai-agents (0.9.0)
+      ruby_llm (~> 1.9.1)
     annotaterb (4.20.0)
       activerecord (>= 6.0.0)
       activesupport (>= 6.0.0)
@@ -314,7 +314,7 @@ GEM
     faraday-net_http_persistent (2.1.0)
       faraday (~> 2.5)
       net-http-persistent (~> 4.0)
-    faraday-retry (2.2.1)
+    faraday-retry (2.4.0)
       faraday (~> 2.0)
     faraday_middleware-aws-sigv4 (1.0.1)
       aws-sigv4 (~> 1.0)
@@ -540,7 +540,7 @@ GEM
       net-imap
       net-pop
       net-smtp
-    marcel (1.0.4)
+    marcel (1.1.0)
     maxminddb (0.1.22)
     meta_request (0.8.5)
       rack-contrib (>= 1.1, < 3)
@@ -559,7 +559,7 @@ GEM
     multi_json (1.15.0)
     multi_xml (0.8.0)
       bigdecimal (>= 3.1, < 5)
-    multipart-post (2.3.0)
+    multipart-post (2.4.1)
     mutex_m (0.3.0)
     neighbor (0.2.3)
       activerecord (>= 5.2)
@@ -825,7 +825,7 @@ GEM
     ruby2ruby (2.5.0)
       ruby_parser (~> 3.1)
       sexp_processor (~> 4.6)
-    ruby_llm (1.8.2)
+    ruby_llm (1.9.2)
       base64
       event_stream_parser (~> 1)
       faraday (>= 1.10.0)
@@ -1004,7 +1004,7 @@ GEM
     working_hours (1.4.1)
       activesupport (>= 3.2)
       tzinfo
-    zeitwerk (2.6.17)
+    zeitwerk (2.7.4)
 
 PLATFORMS
   arm64-darwin-20
@@ -1024,7 +1024,7 @@ DEPENDENCIES
   administrate (>= 0.20.1)
   administrate-field-active_storage (>= 1.0.3)
   administrate-field-belongs_to_search (>= 0.9.0)
-  ai-agents (>= 0.7.0)
+  ai-agents
   annotaterb
   attr_extras
   audited (~> 5.4, >= 5.4.1)
diff --git a/app/controllers/devise_overrides/passwords_controller.rb b/app/controllers/devise_overrides/passwords_controller.rb
index 00976c3cd..c69541f6f 100644
--- a/app/controllers/devise_overrides/passwords_controller.rb
+++ b/app/controllers/devise_overrides/passwords_controller.rb
@@ -6,12 +6,8 @@ class DeviseOverrides::PasswordsController < Devise::PasswordsController
 
   def create
     @user = User.from_email(params[:email])
-    if @user
-      @user.send_reset_password_instructions
-      build_response(I18n.t('messages.reset_password_success'), 200)
-    else
-      build_response(I18n.t('messages.reset_password_failure'), 404)
-    end
+    @user&.send_reset_password_instructions
+    build_response(I18n.t('messages.reset_password'), 200)
   end
 
   def update
diff --git a/app/javascript/dashboard/components-next/NewConversation/ComposeConversation.vue b/app/javascript/dashboard/components-next/NewConversation/ComposeConversation.vue
index ee71bf51a..8e24f3d50 100644
--- a/app/javascript/dashboard/components-next/NewConversation/ComposeConversation.vue
+++ b/app/javascript/dashboard/components-next/NewConversation/ComposeConversation.vue
@@ -1,5 +1,5 @@
 <script setup>
-import { ref, computed, onMounted, watch } from 'vue';
+import { reactive, ref, computed, onMounted, watch } from 'vue';
 import { useStore, useMapGetter } from 'dashboard/composables/store';
 import { useI18n } from 'vue-i18n';
 import { useWindowSize } from '@vueuse/core';
@@ -59,6 +59,23 @@ const isFetchingInboxes = ref(false);
 const isSearching = ref(false);
 const showComposeNewConversation = ref(false);
 
+const formState = reactive({
+  message: '',
+  subject: '',
+  ccEmails: '',
+  bccEmails: '',
+  attachedFiles: [],
+});
+
+const clearFormState = () => {
+  Object.assign(formState, {
+    subject: '',
+    ccEmails: '',
+    bccEmails: '',
+    attachedFiles: [],
+  });
+};
+
 const contactById = useMapGetter('contacts/getContactById');
 const contactsUiFlags = useMapGetter('contacts/getUIFlags');
 const currentUser = useMapGetter('getCurrentUser');
@@ -140,12 +157,14 @@ const handleSelectedContact = async ({ value, action, ...rest }) => {
 
 const handleTargetInbox = inbox => {
   targetInbox.value = inbox;
+  if (!inbox) clearFormState();
   resetContacts();
 };
 
 const clearSelectedContact = () => {
   selectedContact.value = null;
   targetInbox.value = null;
+  clearFormState();
 };
 
 const closeCompose = () => {
@@ -160,6 +179,12 @@ const closeCompose = () => {
   emit('close');
 };
 
+const discardCompose = () => {
+  clearFormState();
+  formState.message = '';
+  closeCompose();
+};
+
 const createConversation = async ({ payload, isFromWhatsApp }) => {
   try {
     const data = await store.dispatch('contactConversations/create', {
@@ -171,7 +196,7 @@ const createConversation = async ({ payload, isFromWhatsApp }) => {
       to: `/app/accounts/${data.account_id}/conversations/${data.id}`,
       message: t('COMPOSE_NEW_CONVERSATION.FORM.GO_TO_CONVERSATION'),
     };
-    closeCompose();
+    discardCompose();
     useAlert(t('COMPOSE_NEW_CONVERSATION.FORM.SUCCESS_MESSAGE'), action);
     return true; // Return success
   } catch (error) {
@@ -193,7 +218,11 @@ watch(
   (currentContact, previousContact) => {
     if (currentContact && props.contactId) {
       // Reset on contact change
-      if (currentContact?.id !== previousContact?.id) clearSelectedContact();
+      if (currentContact?.id !== previousContact?.id) {
+        clearSelectedContact();
+        clearFormState();
+        formState.message = '';
+      }
 
       // First process the contactable inboxes to get the right structure
       const processedInboxes = processContactableInboxes(
@@ -265,6 +294,7 @@ useKeyboardEvents(keyboardEvents);
       @click.self="onModalBackdropClick"
     >
       <ComposeNewConversationForm
+        :form-state="formState"
         :class="[{ 'mt-2': !viewInModal }, composePopoverClass]"
         :contacts="contacts"
         :contact-id="contactId"
@@ -285,7 +315,7 @@ useKeyboardEvents(keyboardEvents);
         @update-target-inbox="handleTargetInbox"
         @clear-selected-contact="clearSelectedContact"
         @create-conversation="createConversation"
-        @discard="closeCompose"
+        @discard="discardCompose"
       />
     </div>
   </div>
diff --git a/app/javascript/dashboard/components-next/NewConversation/components/ComposeNewConversationForm.vue b/app/javascript/dashboard/components-next/NewConversation/components/ComposeNewConversationForm.vue
index 82f87a08d..5ba97b779 100644
--- a/app/javascript/dashboard/components-next/NewConversation/components/ComposeNewConversationForm.vue
+++ b/app/javascript/dashboard/components-next/NewConversation/components/ComposeNewConversationForm.vue
@@ -1,5 +1,5 @@
 <script setup>
-import { reactive, ref, computed } from 'vue';
+import { ref, computed } from 'vue';
 import { useVuelidate } from '@vuelidate/core';
 import { required, requiredIf } from '@vuelidate/validators';
 import { INBOX_TYPES } from 'dashboard/helper/inbox';
@@ -37,6 +37,7 @@ const props = defineProps({
   contactsUiFlags: { type: Object, default: null },
   messageSignature: { type: String, default: '' },
   sendWithSignature: { type: Boolean, default: false },
+  formState: { type: Object, required: true },
 });
 
 const emit = defineEmits([
@@ -57,13 +58,13 @@ const showBccEmailsDropdown = ref(false);
 
 const isCreating = computed(() => props.contactConversationsUiFlags.isCreating);
 
-const state = reactive({
+const state = props.formState || {
   message: '',
   subject: '',
   ccEmails: '',
   bccEmails: '',
   attachedFiles: [],
-});
+};
 
 const inboxTypes = computed(() => ({
   isEmail: props.targetInbox?.channelType === INBOX_TYPES.EMAIL,
diff --git a/app/javascript/dashboard/components-next/message/Message.vue b/app/javascript/dashboard/components-next/message/Message.vue
index 0f6ab85a8..66234984c 100644
--- a/app/javascript/dashboard/components-next/message/Message.vue
+++ b/app/javascript/dashboard/components-next/message/Message.vue
@@ -43,6 +43,7 @@ import VoiceCallBubble from './bubbles/VoiceCall.vue';
 
 import MessageError from './MessageError.vue';
 import ContextMenu from 'dashboard/modules/conversations/components/MessageContextMenu.vue';
+import { useBranding } from 'shared/composables/useBranding';
 
 /**
  * @typedef {Object} Attachment
@@ -143,6 +144,7 @@ const { t } = useI18n();
 const route = useRoute();
 const inboxGetter = useMapGetter('inboxes/getInbox');
 const inbox = computed(() => inboxGetter.value(props.inboxId) || {});
+const { replaceInstallationName } = useBranding();
 
 /**
  * Computes the message variant based on props
@@ -389,13 +391,17 @@ const shouldRenderMessage = computed(() => {
   const isUnsupported = props.contentAttributes?.isUnsupported;
   const isAnIntegrationMessage =
     props.contentType === CONTENT_TYPES.INTEGRATIONS;
+  const isFailedMessage = props.status === MESSAGE_STATUS.FAILED;
+  const hasExternalError = !!props.contentAttributes?.externalError;
 
   return (
     hasAttachments ||
     props.content ||
     isEmailContentType ||
     isUnsupported ||
-    isAnIntegrationMessage
+    isAnIntegrationMessage ||
+    isFailedMessage ||
+    hasExternalError
   );
 });
 
@@ -472,7 +478,7 @@ const avatarInfo = computed(() => {
 
 const avatarTooltip = computed(() => {
   if (props.contentAttributes?.externalEcho) {
-    return t('CONVERSATION.NATIVE_APP_ADVISORY');
+    return replaceInstallationName(t('CONVERSATION.NATIVE_APP_ADVISORY'));
   }
   if (avatarInfo.value.name === '') return '';
   return `${t('CONVERSATION.SENT_BY')} ${avatarInfo.value.name}`;
diff --git a/app/javascript/dashboard/components-next/message/MessageError.vue b/app/javascript/dashboard/components-next/message/MessageError.vue
index cd17c1e3f..fe508c805 100644
--- a/app/javascript/dashboard/components-next/message/MessageError.vue
+++ b/app/javascript/dashboard/components-next/message/MessageError.vue
@@ -12,11 +12,16 @@ defineProps({
 
 const emit = defineEmits(['retry']);
 
-const { orientation, status, createdAt } = useMessageContext();
+const { orientation, status, createdAt, content, attachments } =
+  useMessageContext();
 
 const { t } = useI18n();
 
-const canRetry = computed(() => !hasOneDayPassed(createdAt.value));
+const canRetry = computed(() => {
+  const hasContent = content.value !== null;
+  const hasAttachments = attachments.value && attachments.value.length > 0;
+  return !hasOneDayPassed(createdAt.value) && (hasContent || hasAttachments);
+});
 </script>
 
 <template>
diff --git a/app/javascript/dashboard/components/ChatList.vue b/app/javascript/dashboard/components/ChatList.vue
index 08e2057e4..3b2a66929 100644
--- a/app/javascript/dashboard/components/ChatList.vue
+++ b/app/javascript/dashboard/components/ChatList.vue
@@ -145,6 +145,7 @@ const {
   isConversationSelected,
   onAssignAgent,
   onAssignLabels,
+  onRemoveLabels,
   onAssignTeamsForBulk,
   onUpdateConversations,
 } = useBulkActions();
@@ -859,6 +860,7 @@ provide('deSelectConversation', deSelectConversation);
 provide('assignAgent', onAssignAgent);
 provide('assignTeam', onAssignTeam);
 provide('assignLabels', onAssignLabels);
+provide('removeLabels', onRemoveLabels);
 provide('updateConversationStatus', handleResolveConversation);
 provide('toggleContextMenu', onContextMenuToggle);
 provide('markAsUnread', markAsUnread);
diff --git a/app/javascript/dashboard/components/ConversationItem.vue b/app/javascript/dashboard/components/ConversationItem.vue
index a705dd067..fcd41ad45 100644
--- a/app/javascript/dashboard/components/ConversationItem.vue
+++ b/app/javascript/dashboard/components/ConversationItem.vue
@@ -10,6 +10,7 @@ export default {
     'assignAgent',
     'assignTeam',
     'assignLabels',
+    'removeLabels',
     'updateConversationStatus',
     'toggleContextMenu',
     'markAsUnread',
@@ -63,6 +64,7 @@ export default {
     @assign-agent="assignAgent"
     @assign-team="assignTeam"
     @assign-label="assignLabels"
+    @remove-label="removeLabels"
     @update-conversation-status="updateConversationStatus"
     @context-menu-toggle="toggleContextMenu"
     @mark-as-unread="markAsUnread"
diff --git a/app/javascript/dashboard/components/widgets/WootWriter/Editor.vue b/app/javascript/dashboard/components/widgets/WootWriter/Editor.vue
index 4e0722c25..956e04dda 100644
--- a/app/javascript/dashboard/components/widgets/WootWriter/Editor.vue
+++ b/app/javascript/dashboard/components/widgets/WootWriter/Editor.vue
@@ -28,7 +28,10 @@ import { useAlert } from 'dashboard/composables';
 import { vOnClickOutside } from '@vueuse/components';
 
 import { BUS_EVENTS } from 'shared/constants/busEvents';
-import { CONVERSATION_EVENTS } from 'dashboard/helper/AnalyticsHelper/events';
+import {
+  CONVERSATION_EVENTS,
+  CAPTAIN_EVENTS,
+} from 'dashboard/helper/AnalyticsHelper/events';
 import { MESSAGE_EDITOR_IMAGE_RESIZES } from 'dashboard/constants/editor';
 
 import {
@@ -86,6 +89,7 @@ const props = defineProps({
   // are triggered except when this flag is true
   allowSignature: { type: Boolean, default: false },
   channelType: { type: String, default: '' },
+  conversationId: { type: Number, default: null },
   medium: { type: String, default: '' },
   showImageResizeToolbar: { type: Boolean, default: false }, // A kill switch to show or hide the image toolbar
   focusOnMount: { type: Boolean, default: true },
@@ -396,7 +400,14 @@ function openFileBrowser() {
 }
 
 function handleCopilotClick() {
-  showSelectionMenu.value = !showSelectionMenu.value;
+  const isOpening = !showSelectionMenu.value;
+  if (isOpening) {
+    useTrack(CAPTAIN_EVENTS.EDITOR_AI_MENU_OPENED, {
+      conversationId: props.conversationId,
+      entryPoint: 'inline',
+    });
+  }
+  showSelectionMenu.value = isOpening;
 }
 
 function handleClickOutside(event) {
@@ -819,7 +830,13 @@ useEmitter(BUS_EVENTS.INSERT_INTO_RICH_EDITOR, insertContentIntoEditor);
 </script>
 
 <template>
-  <div ref="editorRoot" class="relative w-full">
+  <div
+    ref="editorRoot"
+    class="relative w-full"
+    :class="{
+      'opacity-50 cursor-not-allowed pointer-events-none': disabled,
+    }"
+  >
     <TagAgents
       v-if="showUserMentions && isPrivate"
       :search-key="mentionSearchKey"
diff --git a/app/javascript/dashboard/components/widgets/WootWriter/ReplyBottomPanel.vue b/app/javascript/dashboard/components/widgets/WootWriter/ReplyBottomPanel.vue
index 5842b7f66..241e65505 100644
--- a/app/javascript/dashboard/components/widgets/WootWriter/ReplyBottomPanel.vue
+++ b/app/javascript/dashboard/components/widgets/WootWriter/ReplyBottomPanel.vue
@@ -122,6 +122,10 @@ export default {
       type: Boolean,
       default: false,
     },
+    isEditorDisabled: {
+      type: Boolean,
+      default: false,
+    },
   },
   emits: [
     'replaceText',
@@ -130,7 +134,7 @@ export default {
     'selectContentTemplate',
     'toggleQuotedReply',
   ],
-  setup() {
+  setup(props) {
     const { setSignatureFlagForInbox, fetchSignatureFlagFromUISettings } =
       useUISettings();
 
@@ -139,6 +143,9 @@ export default {
     const keyboardEvents = {
       '$mod+Alt+KeyA': {
         action: () => {
+          // Skip if editor is disabled (e.g., WhatsApp 24-hour window expired)
+          if (props.isEditorDisabled) return;
+
           // TODO: This is really hacky, we need to replace the file picker component with
           // a custom one, where the logic and the component markup is isolated.
           // Once we have the custom component, we can remove the hacky logic below.
@@ -146,7 +153,7 @@ export default {
           const uploadTriggerButton = document.querySelector(
             '#conversationAttachment'
           );
-          uploadTriggerButton.click();
+          if (uploadTriggerButton) uploadTriggerButton.click();
         },
         allowOnFocusedInput: true,
       },
@@ -177,9 +184,11 @@ export default {
       };
     },
     showAttachButton() {
+      if (this.isEditorDisabled) return false;
       return this.showFileUpload || this.isNote;
     },
     showAudioRecorderButton() {
+      if (this.isEditorDisabled) return false;
       if (this.isALineChannel) {
         return false;
       }
@@ -197,6 +206,7 @@ export default {
       );
     },
     showAudioPlayStopButton() {
+      if (this.isEditorDisabled) return false;
       return this.showAudioRecorder && this.isRecordingAudio;
     },
     isInstagramDM() {
@@ -236,6 +246,7 @@ export default {
       }
     },
     showMessageSignatureButton() {
+      if (this.isEditorDisabled) return false;
       return !this.isOnPrivateNote;
     },
     sendWithSignature() {
@@ -280,6 +291,7 @@ export default {
   <div class="flex justify-between p-3" :class="wrapClass">
     <div class="left-wrap">
       <NextButton
+        v-if="!isEditorDisabled"
         v-tooltip.top-end="$t('CONVERSATION.REPLYBOX.TIP_EMOJI_ICON')"
         icon="i-ph-smiley-sticker"
         slate
@@ -288,6 +300,7 @@ export default {
         @click="toggleEmojiPicker"
       />
       <FileUpload
+        v-if="showAttachButton"
         ref="uploadRef"
         v-tooltip.top-end="$t('CONVERSATION.REPLYBOX.TIP_ATTACH_ICON')"
         input-id="conversationAttachment"
diff --git a/app/javascript/dashboard/components/widgets/WootWriter/ReplyTopPanel.vue b/app/javascript/dashboard/components/widgets/WootWriter/ReplyTopPanel.vue
index 0912cc698..ae49145dc 100644
--- a/app/javascript/dashboard/components/widgets/WootWriter/ReplyTopPanel.vue
+++ b/app/javascript/dashboard/components/widgets/WootWriter/ReplyTopPanel.vue
@@ -2,8 +2,10 @@
 import { ref } from 'vue';
 import { useKeyboardEvents } from 'dashboard/composables/useKeyboardEvents';
 import { useCaptain } from 'dashboard/composables/useCaptain';
+import { useTrack } from 'dashboard/composables';
 import { vOnClickOutside } from '@vueuse/components';
 import { REPLY_EDITOR_MODES, CHAR_LENGTH_WARNING } from './constants';
+import { CAPTAIN_EVENTS } from 'dashboard/helper/AnalyticsHelper/events';
 import NextButton from 'dashboard/components-next/button/Button.vue';
 import EditorModeToggle from './EditorModeToggle.vue';
 import CopilotMenuBar from './CopilotMenuBar.vue';
@@ -31,6 +33,14 @@ export default {
       type: Boolean,
       default: false,
     },
+    isEditorDisabled: {
+      type: Boolean,
+      default: false,
+    },
+    conversationId: {
+      type: Number,
+      default: null,
+    },
     isMessageLengthReachingThreshold: {
       type: Boolean,
       default: () => false,
@@ -69,7 +79,14 @@ export default {
     };
 
     const toggleCopilotMenu = () => {
-      showCopilotMenu.value = !showCopilotMenu.value;
+      const isOpening = !showCopilotMenu.value;
+      if (isOpening) {
+        useTrack(CAPTAIN_EVENTS.EDITOR_AI_MENU_OPENED, {
+          conversationId: props.conversationId,
+          entryPoint: 'top_panel',
+        });
+      }
+      showCopilotMenu.value = isOpening;
     };
 
     const handleClickOutside = () => {
@@ -144,7 +161,7 @@ export default {
       <div class="relative">
         <NextButton
           ghost
-          :disabled="disabled"
+          :disabled="disabled || isEditorDisabled"
           :class="{
             'text-n-violet-9 hover:enabled:!bg-n-violet-3': !showCopilotMenu,
             'text-n-violet-9 bg-n-violet-3': showCopilotMenu,
diff --git a/app/javascript/dashboard/components/widgets/conversation/ConversationCard.vue b/app/javascript/dashboard/components/widgets/conversation/ConversationCard.vue
index 5093e5c4b..9f7805b4e 100644
--- a/app/javascript/dashboard/components/widgets/conversation/ConversationCard.vue
+++ b/app/javascript/dashboard/components/widgets/conversation/ConversationCard.vue
@@ -34,6 +34,7 @@ const emit = defineEmits([
   'contextMenuToggle',
   'assignAgent',
   'assignLabel',
+  'removeLabel',
   'assignTeam',
   'markAsUnread',
   'markAsRead',
@@ -203,7 +204,10 @@ const onAssignAgent = agent => {
 
 const onAssignLabel = label => {
   emit('assignLabel', [label.title], [props.chat.id]);
-  closeContextMenu();
+};
+
+const onRemoveLabel = label => {
+  emit('removeLabel', [label.title], [props.chat.id]);
 };
 
 const onAssignTeam = team => {
@@ -379,11 +383,13 @@ const deleteConversation = () => {
         :priority="chat.priority"
         :chat-id="chat.id"
         :has-unread-messages="hasUnread"
+        :conversation-labels="chat.labels"
         :conversation-url="conversationPath"
         :allowed-options="allowedContextMenuOptions"
         @update-conversation="onUpdateConversation"
         @assign-agent="onAssignAgent"
         @assign-label="onAssignLabel"
+        @remove-label="onRemoveLabel"
         @assign-team="onAssignTeam"
         @mark-as-unread="markAsUnread"
         @mark-as-read="markAsRead"
diff --git a/app/javascript/dashboard/components/widgets/conversation/ReplyBox.vue b/app/javascript/dashboard/components/widgets/conversation/ReplyBox.vue
index e9d2f6d08..78a2481e9 100644
--- a/app/javascript/dashboard/components/widgets/conversation/ReplyBox.vue
+++ b/app/javascript/dashboard/components/widgets/conversation/ReplyBox.vue
@@ -41,7 +41,10 @@ import {
   truncatePreviewText,
   appendQuotedTextToMessage,
 } from 'dashboard/helper/quotedEmailHelper';
-import { CONVERSATION_EVENTS } from '../../../helper/AnalyticsHelper/events';
+import {
+  CONVERSATION_EVENTS,
+  CAPTAIN_EVENTS,
+} from '../../../helper/AnalyticsHelper/events';
 import fileUploadMixin from 'dashboard/mixins/fileUploadMixin';
 import {
   appendSignature,
@@ -136,6 +139,7 @@ export default {
       newConversationModalActive: false,
       showArticleSearchPopover: false,
       hasRecordedAudio: false,
+      copilotAcceptedMessages: {},
     };
   },
   computed: {
@@ -195,6 +199,11 @@ export default {
       return this.$store.getters['inboxes/getInbox'](this.inboxId);
     },
     messagePlaceHolder() {
+      if (this.isEditorDisabled) {
+        return this.isAWhatsAppChannel
+          ? this.$t('CONVERSATION.FOOTER.MESSAGING_RESTRICTED_WHATSAPP')
+          : this.$t('CONVERSATION.FOOTER.MESSAGING_RESTRICTED');
+      }
       return this.isPrivate
         ? this.$t('CONVERSATION.FOOTER.PRIVATE_MSG_INPUT')
         : this.$t('CONVERSATION.FOOTER.MSG_INPUT');
@@ -206,6 +215,7 @@ export default {
       return this.maxLength - this.message.length;
     },
     isReplyButtonDisabled() {
+      if (this.isEditorDisabled) return true;
       if (this.isATwitterInbox) return true;
       if (this.hasAttachments || this.hasRecordedAudio) return false;
 
@@ -414,6 +424,13 @@ export default {
     isDefaultEditorMode() {
       return !this.showAudioRecorderEditor && !this.copilot.isActive.value;
     },
+    isEditorDisabled() {
+      return (
+        this.isAWhatsAppChannel &&
+        !this.isOnPrivateNote &&
+        !this.currentChat.can_reply
+      );
+    },
   },
   watch: {
     currentChat(conversation, oldConversation) {
@@ -508,6 +525,24 @@ export default {
     emitter.off(CMD_AI_ASSIST, this.executeCopilotAction);
   },
   methods: {
+    getDraftKey(
+      conversationId = this.conversationIdByRoute,
+      replyType = this.replyType
+    ) {
+      return `draft-${conversationId}-${replyType}`;
+    },
+    getCopilotAcceptedMessage(replyType = this.replyType) {
+      const key = this.getDraftKey(this.conversationIdByRoute, replyType);
+      return this.copilotAcceptedMessages[key] || '';
+    },
+    setCopilotAcceptedMessage(message, replyType = this.replyType) {
+      const key = this.getDraftKey(this.conversationIdByRoute, replyType);
+      this.copilotAcceptedMessages[key] = trimContent(message || '');
+    },
+    clearCopilotAcceptedMessage(replyType = this.replyType) {
+      const key = this.getDraftKey(this.conversationIdByRoute, replyType);
+      delete this.copilotAcceptedMessages[key];
+    },
     handleInsert(article) {
       const { url, title } = article;
       // Removing empty lines from the title
@@ -559,7 +594,7 @@ export default {
     },
     saveDraft(conversationId, replyType) {
       if (this.message || this.message === '') {
-        const key = `draft-${conversationId}-${replyType}`;
+        const key = this.getDraftKey(conversationId, replyType);
         const draftToSave = trimContent(this.message || '');
 
         this.$store.dispatch('draftMessages/set', {
@@ -574,7 +609,7 @@ export default {
     },
     getFromDraft() {
       if (this.conversationIdByRoute) {
-        const key = `draft-${this.conversationIdByRoute}-${this.replyType}`;
+        const key = this.getDraftKey();
         const messageFromStore =
           this.$store.getters['draftMessages/get'](key) || '';
 
@@ -597,7 +632,7 @@ export default {
     },
     removeFromDraft() {
       if (this.conversationIdByRoute) {
-        const key = `draft-${this.conversationIdByRoute}-${this.replyType}`;
+        const key = this.getDraftKey();
         this.$store.dispatch('draftMessages/delete', { key });
       }
     },
@@ -655,6 +690,9 @@ export default {
       // Don't handle paste if compose new conversation modal is open
       if (this.newConversationModalActive) return;
 
+      // Don't handle paste if editor is disabled
+      if (this.isEditorDisabled) return;
+
       // Filter valid files (non-zero size)
       Array.from(e.clipboardData.files)
         .filter(file => file.size > 0)
@@ -708,6 +746,7 @@ export default {
         return;
       }
       if (!this.showMentions) {
+        const copilotAcceptedMessage = this.getCopilotAcceptedMessage();
         const isOnWhatsApp =
           this.isATwilioWhatsAppChannel ||
           this.isAWhatsAppCloudChannel ||
@@ -717,10 +756,17 @@ export default {
         // This can create duplicate messages in Chatwoot. To prevent this issue, we'll handle text and attachments as separate messages.
         const isOnInstagram = this.isAnInstagramChannel;
         if ((isOnWhatsApp || isOnInstagram) && !this.isPrivate) {
-          this.sendMessageAsMultipleMessages(this.message);
+          this.sendMessageAsMultipleMessages(
+            this.message,
+            copilotAcceptedMessage
+          );
         } else {
           const messagePayload = this.getMessagePayload(this.message);
-          this.sendMessage(messagePayload);
+          this.sendMessage(
+            messagePayload,
+            this.message,
+            copilotAcceptedMessage
+          );
         }
 
         if (!this.isPrivate) {
@@ -732,13 +778,53 @@ export default {
         this.$emit('update:popOutReplyBox', false);
       }
     },
-    sendMessageAsMultipleMessages(message) {
+    sendMessageAsMultipleMessages(message, copilotAcceptedMessage = '') {
       const messages = this.getMultipleMessagesPayload(message);
       messages.forEach(messagePayload => {
-        this.sendMessage(messagePayload);
+        this.sendMessage(
+          messagePayload,
+          messagePayload.message || '',
+          copilotAcceptedMessage
+        );
       });
     },
-    sendMessageAnalyticsData(isPrivate) {
+    sendMessageAnalyticsData(
+      isPrivate,
+      { editorMessage = '', copilotAcceptedMessage = '' } = {}
+    ) {
+      const normalizeForComparison = message => {
+        let normalizedMessage = message || '';
+
+        if (this.sendWithSignature && this.messageSignature && !isPrivate) {
+          const effectiveChannelType = getEffectiveChannelType(
+            this.channelType,
+            this.inbox?.medium || ''
+          );
+          normalizedMessage = removeSignature(
+            normalizedMessage,
+            this.messageSignature,
+            effectiveChannelType
+          );
+        }
+
+        return trimContent(normalizedMessage);
+      };
+
+      const normalizedAcceptedMessage = normalizeForComparison(
+        copilotAcceptedMessage
+      );
+      const normalizedEditorMessage = normalizeForComparison(editorMessage);
+
+      if (normalizedAcceptedMessage && normalizedEditorMessage) {
+        useTrack(CAPTAIN_EVENTS.AI_ASSISTED_MESSAGE_SENT, {
+          conversationId: this.conversationIdByRoute,
+          channelType: this.channelType,
+          editedBeforeSend:
+            normalizedAcceptedMessage !== normalizedEditorMessage,
+          isPrivate,
+        });
+      }
+
       // Analytics data for message signature is enabled or not in channels
       return isPrivate
         ? useTrack(CONVERSATION_EVENTS.SENT_PRIVATE_NOTE)
@@ -772,7 +858,11 @@ export default {
         this.confirmOnSendReply();
       }
     },
-    async sendMessage(messagePayload) {
+    async sendMessage(
+      messagePayload,
+      editorMessage = '',
+      copilotAcceptedMessage = ''
+    ) {
       try {
         await this.$store.dispatch(
           'createPendingMessageAndSend',
@@ -781,7 +871,10 @@ export default {
         emitter.emit(BUS_EVENTS.SCROLL_TO_MESSAGE);
         emitter.emit(BUS_EVENTS.MESSAGE_SENT);
         this.removeFromDraft();
-        this.sendMessageAnalyticsData(messagePayload.private);
+        this.sendMessageAnalyticsData(messagePayload.private, {
+          editorMessage,
+          copilotAcceptedMessage,
+        });
       } catch (error) {
         const errorMessage =
           error?.response?.data?.error || this.$t('CONVERSATION.MESSAGE_ERROR');
@@ -855,6 +948,7 @@ export default {
     },
     clearMessage() {
       this.message = '';
+      this.clearCopilotAcceptedMessage();
       if (this.sendWithSignature && !this.isPrivate) {
         // if signature is enabled, append it to the message
         const effectiveChannelType = getEffectiveChannelType(
@@ -1119,7 +1213,9 @@ export default {
       this.$emit('update:popOutReplyBox', !this.popOutReplyBox);
     },
     onSubmitCopilotReply() {
-      this.message = this.copilot.accept();
+      const acceptedMessage = this.copilot.accept();
+      this.message = acceptedMessage;
+      this.setCopilotAcceptedMessage(acceptedMessage);
     },
   },
 };
@@ -1130,11 +1226,13 @@ export default {
   <div ref="replyEditor" class="reply-box" :class="replyBoxClass">
     <ReplyTopPanel
       :mode="replyType"
+      :conversation-id="conversationId"
       :is-reply-restricted="isReplyRestricted"
       :disabled="
         (copilot.isActive.value && copilot.isButtonDisabled.value) ||
         showAudioRecorderEditor
       "
+      :is-editor-disabled="isEditorDisabled"
       :is-message-length-reaching-threshold="isMessageLengthReachingThreshold"
       :characters-remaining="charactersRemaining"
       :popout-reply-box="popOutReplyBox"
@@ -1204,12 +1302,14 @@ export default {
         <WootMessageEditor
           v-else-if="!showAudioRecorderEditor"
           v-model="message"
+          :conversation-id="conversationId"
           :editor-id="editorStateId"
           class="input popover-prosemirror-menu"
           :is-private="isOnPrivateNote"
           :placeholder="messagePlaceHolder"
           :update-selection-with="updateEditorSelectionWith"
           :min-height="4"
+          :disabled="isEditorDisabled"
           enable-variables
           :variables="messageVariables"
           :signature="messageSignature"
@@ -1285,6 +1385,7 @@ export default {
         :is-recording-audio="isRecordingAudio"
         :is-send-disabled="isReplyButtonDisabled"
         :is-note="isPrivate"
+        :is-editor-disabled="isEditorDisabled"
         :on-file-upload="onFileUpload"
         :on-send="onSendReply"
         :conversation-type="conversationType"
diff --git a/app/javascript/dashboard/components/widgets/conversation/contextMenu/Index.vue b/app/javascript/dashboard/components/widgets/conversation/contextMenu/Index.vue
index a6f79500a..34009935c 100644
--- a/app/javascript/dashboard/components/widgets/conversation/contextMenu/Index.vue
+++ b/app/javascript/dashboard/components/widgets/conversation/contextMenu/Index.vue
@@ -53,6 +53,10 @@ export default {
       type: String,
       default: null,
     },
+    conversationLabels: {
+      type: Array,
+      default: () => [],
+    },
     conversationUrl: {
       type: String,
       default: '',
@@ -70,6 +74,7 @@ export default {
     'assignAgent',
     'assignTeam',
     'assignLabel',
+    'removeLabel',
     'deleteConversation',
     'close',
   ],
@@ -334,8 +339,16 @@ export default {
           v-for="label in labels"
           :key="label.id"
           :option="generateMenuLabelConfig(label, 'label')"
-          variant="label"
-          @click.stop="$emit('assignLabel', label)"
+          :variant="
+            conversationLabels.includes(label.title)
+              ? 'label-assigned'
+              : 'label'
+          "
+          @click.stop="
+            conversationLabels.includes(label.title)
+              ? $emit('removeLabel', label)
+              : $emit('assignLabel', label)
+          "
         />
       </MenuItemWithSubmenu>
       <MenuItemWithSubmenu
diff --git a/app/javascript/dashboard/components/widgets/conversation/contextMenu/menuItem.vue b/app/javascript/dashboard/components/widgets/conversation/contextMenu/menuItem.vue
index 9b1c9b0fb..ace2433ed 100644
--- a/app/javascript/dashboard/components/widgets/conversation/contextMenu/menuItem.vue
+++ b/app/javascript/dashboard/components/widgets/conversation/contextMenu/menuItem.vue
@@ -1,5 +1,6 @@
 <script setup>
 import Avatar from 'dashboard/components-next/avatar/Avatar.vue';
+import Icon from 'dashboard/components-next/icon/Icon.vue';
 
 defineProps({
   option: {
@@ -22,7 +23,9 @@ defineProps({
       class="flex-shrink-0"
     />
     <span
-      v-if="variant === 'label' && option.color"
+      v-if="
+        (variant === 'label' || variant === 'label-assigned') && option.color
+      "
       class="label-pill flex-shrink-0"
       :style="{ backgroundColor: option.color }"
     />
@@ -37,6 +40,11 @@ defineProps({
     <p class="menu-label truncate min-w-0 flex-1">
       {{ option.label }}
     </p>
+    <Icon
+      v-if="variant === 'label-assigned'"
+      icon="i-lucide-check"
+      class="flex-shrink-0 size-3.5 mr-1"
+    />
   </div>
 </template>
 
diff --git a/app/javascript/dashboard/components/widgets/conversation/conversation/LabelSuggestion.vue b/app/javascript/dashboard/components/widgets/conversation/conversation/LabelSuggestion.vue
index 9075eb4ed..0c8a4fb57 100644
--- a/app/javascript/dashboard/components/widgets/conversation/conversation/LabelSuggestion.vue
+++ b/app/javascript/dashboard/components/widgets/conversation/conversation/LabelSuggestion.vue
@@ -2,6 +2,7 @@
 // components
 import NextButton from 'dashboard/components-next/button/Button.vue';
 import Avatar from 'dashboard/components-next/avatar/Avatar.vue';
+import { useBranding } from 'shared/composables/useBranding';
 
 // composables
 import { useCaptain } from 'dashboard/composables/useCaptain';
@@ -34,8 +35,9 @@ export default {
   },
   setup() {
     const { captainTasksEnabled } = useCaptain();
+    const { replaceInstallationName } = useBranding();
 
-    return { captainTasksEnabled };
+    return { captainTasksEnabled, replaceInstallationName };
   },
   data() {
     return {
@@ -228,7 +230,9 @@ export default {
       <div class="sender--info has-tooltip" data-original-title="null">
         <Avatar
           v-tooltip.top="{
-            content: $t('LABEL_MGMT.SUGGESTIONS.POWERED_BY'),
+            content: replaceInstallationName(
+              $t('LABEL_MGMT.SUGGESTIONS.POWERED_BY')
+            ),
             delay: { show: 600, hide: 0 },
             hideOnClick: true,
           }"
diff --git a/app/javascript/dashboard/composables/captain/constants.js b/app/javascript/dashboard/composables/captain/constants.js
new file mode 100644
index 000000000..98629a94f
--- /dev/null
+++ b/app/javascript/dashboard/composables/captain/constants.js
@@ -0,0 +1,12 @@
+export const CAPTAIN_ERROR_TYPES = Object.freeze({
+  ABORTED: 'aborted',
+  API_ERROR: 'api_error',
+  HTTP_PREFIX: 'http_',
+  ABORT_ERROR: 'AbortError',
+  CANCELED_ERROR: 'CanceledError',
+});
+
+export const CAPTAIN_GENERATION_FAILURE_REASONS = Object.freeze({
+  EMPTY_RESPONSE: 'empty_response',
+  EXCEPTION: 'exception',
+});
diff --git a/app/javascript/dashboard/composables/chatlist/useBulkActions.js b/app/javascript/dashboard/composables/chatlist/useBulkActions.js
index a32c4c512..45421b978 100644
--- a/app/javascript/dashboard/composables/chatlist/useBulkActions.js
+++ b/app/javascript/dashboard/composables/chatlist/useBulkActions.js
@@ -102,6 +102,28 @@ export function useBulkActions() {
     }
   }
 
+  // Only used in context menu
+  async function onRemoveLabels(labelsToRemove, conversationId = null) {
+    try {
+      await store.dispatch('bulkActions/process', {
+        type: 'Conversation',
+        ids: conversationId || selectedConversations.value,
+        labels: {
+          remove: labelsToRemove,
+        },
+      });
+
+      useAlert(
+        t('CONVERSATION.CARD_CONTEXT_MENU.API.LABEL_REMOVAL.SUCCESFUL', {
+          labelName: labelsToRemove[0],
+          conversationId,
+        })
+      );
+    } catch (err) {
+      useAlert(t('CONVERSATION.CARD_CONTEXT_MENU.API.LABEL_REMOVAL.FAILED'));
+    }
+  }
+
   async function onAssignTeamsForBulk(team) {
     try {
       await store.dispatch('bulkActions/process', {
@@ -189,6 +211,7 @@ export function useBulkActions() {
     isConversationSelected,
     onAssignAgent,
     onAssignLabels,
+    onRemoveLabels,
     onAssignTeamsForBulk,
     onUpdateConversations,
   };
diff --git a/app/javascript/dashboard/composables/useCaptain.js b/app/javascript/dashboard/composables/useCaptain.js
index f7c72e04f..b9648fdd0 100644
--- a/app/javascript/dashboard/composables/useCaptain.js
+++ b/app/javascript/dashboard/composables/useCaptain.js
@@ -11,6 +11,7 @@ import { useAlert } from 'dashboard/composables';
 import { useI18n } from 'vue-i18n';
 import { FEATURE_FLAGS } from 'dashboard/featureFlags';
 import TasksAPI from 'dashboard/api/captain/tasks';
+import { CAPTAIN_ERROR_TYPES } from 'dashboard/composables/captain/constants';
 
 export function useCaptain() {
   const store = useStore();
@@ -69,7 +70,10 @@ export function useCaptain() {
    * @param {Error} error - The error object from the API call.
    */
   const handleAPIError = error => {
-    if (error.name === 'AbortError' || error.name === 'CanceledError') {
+    if (
+      error.name === CAPTAIN_ERROR_TYPES.ABORT_ERROR ||
+      error.name === CAPTAIN_ERROR_TYPES.CANCELED_ERROR
+    ) {
       return;
     }
     const errorMessage =
@@ -78,6 +82,24 @@ export function useCaptain() {
     useAlert(errorMessage);
   };
 
+  /**
+   * Classifies API error types for downstream analytics.
+   * @param {Error} error
+   * @returns {string}
+   */
+  const getErrorType = error => {
+    if (
+      error.name === CAPTAIN_ERROR_TYPES.ABORT_ERROR ||
+      error.name === CAPTAIN_ERROR_TYPES.CANCELED_ERROR
+    ) {
+      return CAPTAIN_ERROR_TYPES.ABORTED;
+    }
+    if (error.response?.status) {
+      return `${CAPTAIN_ERROR_TYPES.HTTP_PREFIX}${error.response.status}`;
+    }
+    return CAPTAIN_ERROR_TYPES.API_ERROR;
+  };
+
   // === Task Methods ===
   /**
    * Rewrites content with a specific operation.
@@ -103,7 +125,7 @@ export function useCaptain() {
       return { message: generatedMessage, followUpContext };
     } catch (error) {
       handleAPIError(error);
-      return { message: '' };
+      return { message: '', errorType: getErrorType(error) };
     }
   };
 
@@ -125,7 +147,7 @@ export function useCaptain() {
       return { message: generatedMessage, followUpContext };
     } catch (error) {
       handleAPIError(error);
-      return { message: '' };
+      return { message: '', errorType: getErrorType(error) };
     }
   };
 
@@ -147,7 +169,7 @@ export function useCaptain() {
       return { message: generatedMessage, followUpContext };
     } catch (error) {
       handleAPIError(error);
-      return { message: '' };
+      return { message: '', errorType: getErrorType(error) };
     }
   };
 
@@ -171,7 +193,11 @@ export function useCaptain() {
       return { message: generatedMessage, followUpContext: updatedContext };
     } catch (error) {
       handleAPIError(error);
-      return { message: '', followUpContext };
+      return {
+        message: '',
+        followUpContext,
+        errorType: getErrorType(error),
+      };
     }
   };
 
diff --git a/app/javascript/dashboard/composables/useCopilotReply.js b/app/javascript/dashboard/composables/useCopilotReply.js
index 492bcb43e..42f506b16 100644
--- a/app/javascript/dashboard/composables/useCopilotReply.js
+++ b/app/javascript/dashboard/composables/useCopilotReply.js
@@ -3,6 +3,10 @@ import { useCaptain } from 'dashboard/composables/useCaptain';
 import { useUISettings } from 'dashboard/composables/useUISettings';
 import { useTrack } from 'dashboard/composables';
 import { CAPTAIN_EVENTS } from 'dashboard/helper/AnalyticsHelper/events';
+import {
+  CAPTAIN_ERROR_TYPES,
+  CAPTAIN_GENERATION_FAILURE_REASONS,
+} from 'dashboard/composables/captain/constants';
 
 // Actions that map to REWRITE events (with operation attribute)
 const REWRITE_ACTIONS = [
@@ -52,6 +56,20 @@ function buildPayload(action, conversationId, followUpCount = undefined) {
   return payload;
 }
 
+function trackGenerationFailure({
+  action,
+  conversationId,
+  followUpCount = undefined,
+  stage,
+  reason,
+}) {
+  useTrack(CAPTAIN_EVENTS.GENERATION_FAILED, {
+    ...buildPayload(action, conversationId, followUpCount),
+    stage,
+    reason,
+  });
+}
+
 /**
  * Composable for managing Copilot reply generation state and actions.
  * Extracts copilot-related logic from ReplyBox for cleaner code organization.
@@ -146,7 +164,8 @@ export function useCopilotReply() {
 
     // Reset without tracking dismiss (starting new action)
     reset(false);
-    abortController.value = new AbortController();
+    const requestController = new AbortController();
+    abortController.value = requestController;
     isGenerating.value = true;
     isContentReady.value = false;
     currentAction.value = action;
@@ -154,28 +173,66 @@ export function useCopilotReply() {
     trackedConversationId.value = conversationId.value;
 
     try {
-      const { message: content, followUpContext: newContext } =
-        await processEvent(action, data, {
-          signal: abortController.value.signal,
-        });
+      const {
+        message: content,
+        followUpContext: newContext,
+        errorType,
+      } = await processEvent(action, data, {
+        signal: requestController.signal,
+      });
 
-      if (!abortController.value?.signal.aborted) {
-        generatedContent.value = content;
-        followUpContext.value = newContext;
-        if (content) {
-          showEditor.value = true;
-          // Track "Used" event on successful generation
-          const eventKey = `${getEventPrefix(action)}_USED`;
-          useTrack(
-            CAPTAIN_EVENTS[eventKey],
-            buildPayload(action, trackedConversationId.value)
-          );
+      if (requestController.signal.aborted) return;
+      if (errorType === CAPTAIN_ERROR_TYPES.ABORTED) {
+        if (abortController.value === requestController) {
+          isGenerating.value = false;
         }
-        isGenerating.value = false;
+        return;
       }
-    } catch {
-      if (!abortController.value?.signal.aborted) {
-        isGenerating.value = false;
+
+      generatedContent.value = content;
+      followUpContext.value = newContext;
+      if (content) {
+        showEditor.value = true;
+        // Track "Used" event on successful generation
+        const eventKey = `${getEventPrefix(action)}_USED`;
+        useTrack(
+          CAPTAIN_EVENTS[eventKey],
+          buildPayload(action, trackedConversationId.value)
+        );
+      } else if (errorType && errorType !== CAPTAIN_ERROR_TYPES.ABORTED) {
+        trackGenerationFailure({
+          action,
+          conversationId: trackedConversationId.value,
+          stage: 'initial',
+          reason: errorType,
+        });
+      } else {
+        trackGenerationFailure({
+          action,
+          conversationId: trackedConversationId.value,
+          stage: 'initial',
+          reason: CAPTAIN_GENERATION_FAILURE_REASONS.EMPTY_RESPONSE,
+        });
+      }
+      isGenerating.value = false;
+    } catch (error) {
+      if (
+        requestController.signal.aborted ||
+        error?.name === CAPTAIN_ERROR_TYPES.ABORT_ERROR ||
+        error?.name === CAPTAIN_ERROR_TYPES.CANCELED_ERROR
+      ) {
+        return;
+      }
+      trackGenerationFailure({
+        action,
+        conversationId: trackedConversationId.value,
+        stage: 'initial',
+        reason: error?.name || CAPTAIN_GENERATION_FAILURE_REASONS.EXCEPTION,
+      });
+      isGenerating.value = false;
+    } finally {
+      if (abortController.value === requestController) {
+        abortController.value = null;
       }
     }
   }
@@ -187,7 +244,8 @@ export function useCopilotReply() {
   async function sendFollowUp(message) {
     if (!followUpContext.value || !message.trim()) return;
 
-    abortController.value = new AbortController();
+    const requestController = new AbortController();
+    abortController.value = requestController;
     isGenerating.value = true;
     isContentReady.value = false;
 
@@ -198,24 +256,65 @@ export function useCopilotReply() {
     followUpCount.value += 1;
 
     try {
-      const { message: content, followUpContext: updatedContext } =
-        await followUp({
-          followUpContext: followUpContext.value,
-          message,
-          signal: abortController.value.signal,
-        });
+      const {
+        message: content,
+        followUpContext: updatedContext,
+        errorType,
+      } = await followUp({
+        followUpContext: followUpContext.value,
+        message,
+        signal: requestController.signal,
+      });
 
-      if (!abortController.value?.signal.aborted) {
-        if (content) {
-          generatedContent.value = content;
-          followUpContext.value = updatedContext;
-          showEditor.value = true;
+      if (requestController.signal.aborted) return;
+      if (errorType === CAPTAIN_ERROR_TYPES.ABORTED) {
+        if (abortController.value === requestController) {
+          isGenerating.value = false;
         }
-        isGenerating.value = false;
+        return;
       }
-    } catch {
-      if (!abortController.value?.signal.aborted) {
-        isGenerating.value = false;
+
+      if (content) {
+        generatedContent.value = content;
+        followUpContext.value = updatedContext;
+        showEditor.value = true;
+      } else if (errorType && errorType !== CAPTAIN_ERROR_TYPES.ABORTED) {
+        trackGenerationFailure({
+          action: currentAction.value,
+          conversationId: trackedConversationId.value,
+          followUpCount: followUpCount.value,
+          stage: 'follow_up',
+          reason: errorType,
+        });
+      } else {
+        trackGenerationFailure({
+          action: currentAction.value,
+          conversationId: trackedConversationId.value,
+          followUpCount: followUpCount.value,
+          stage: 'follow_up',
+          reason: CAPTAIN_GENERATION_FAILURE_REASONS.EMPTY_RESPONSE,
+        });
+      }
+      isGenerating.value = false;
+    } catch (error) {
+      if (
+        requestController.signal.aborted ||
+        error?.name === CAPTAIN_ERROR_TYPES.ABORT_ERROR ||
+        error?.name === CAPTAIN_ERROR_TYPES.CANCELED_ERROR
+      ) {
+        return;
+      }
+      trackGenerationFailure({
+        action: currentAction.value,
+        conversationId: trackedConversationId.value,
+        followUpCount: followUpCount.value,
+        stage: 'follow_up',
+        reason: error?.name || CAPTAIN_GENERATION_FAILURE_REASONS.EXCEPTION,
+      });
+      isGenerating.value = false;
+    } finally {
+      if (abortController.value === requestController) {
+        abortController.value = null;
       }
     }
   }
diff --git a/app/javascript/dashboard/helper/AnalyticsHelper/events.js b/app/javascript/dashboard/helper/AnalyticsHelper/events.js
index 0b6e85d77..c9fefb129 100644
--- a/app/javascript/dashboard/helper/AnalyticsHelper/events.js
+++ b/app/javascript/dashboard/helper/AnalyticsHelper/events.js
@@ -85,6 +85,11 @@ export const PORTALS_EVENTS = Object.freeze({
 });
 
 export const CAPTAIN_EVENTS = Object.freeze({
+  // Editor funnel events
+  EDITOR_AI_MENU_OPENED: 'Captain: Editor AI menu opened',
+  GENERATION_FAILED: 'Captain: Generation failed',
+  AI_ASSISTED_MESSAGE_SENT: 'Captain: AI-assisted message sent',
+
   // Rewrite events (with operation attribute in payload)
   REWRITE_USED: 'Captain: Rewrite used',
   REWRITE_APPLIED: 'Captain: Rewrite applied',
diff --git a/app/javascript/dashboard/i18n/locale/en/conversation.json b/app/javascript/dashboard/i18n/locale/en/conversation.json
index 99e0bb072..951a46993 100644
--- a/app/javascript/dashboard/i18n/locale/en/conversation.json
+++ b/app/javascript/dashboard/i18n/locale/en/conversation.json
@@ -174,6 +174,10 @@
           "SUCCESFUL": "Assigned label #{labelName} to conversation id {conversationId}",
           "FAILED": "Couldn't assign label. Please try again."
         },
+        "LABEL_REMOVAL": {
+          "SUCCESFUL": "Removed label #{labelName} from conversation id {conversationId}",
+          "FAILED": "Couldn't remove label. Please try again."
+        },
         "TEAM_ASSIGNMENT": {
           "SUCCESFUL": "Assigned team \"{team}\" to conversation id {conversationId}",
           "FAILED": "Couldn't assign team. Please try again."
@@ -186,6 +190,8 @@
       "DISABLE_SIGN_TOOLTIP": "Disable signature",
       "MSG_INPUT": "Shift + enter for new line. Start with '/' to select a Canned Response.",
       "PRIVATE_MSG_INPUT": "Shift + enter for new line. This will be visible only to Agents",
+      "MESSAGING_RESTRICTED": "You cannot reply to this conversation",
+      "MESSAGING_RESTRICTED_WHATSAPP": "You can only reply using a template message due to 24-hour message window restriction",
       "MESSAGE_SIGNATURE_NOT_CONFIGURED": "Message signature is not configured, please configure it in profile settings.",
       "COPILOT_MSG_INPUT": "Give copilot additional prompts, or ask anything else... Press enter to send follow-up",
       "CLICK_HERE": "Click here to update",
diff --git a/app/models/concerns/auto_assignment_handler.rb b/app/models/concerns/auto_assignment_handler.rb
index a1198200a..dca154842 100644
--- a/app/models/concerns/auto_assignment_handler.rb
+++ b/app/models/concerns/auto_assignment_handler.rb
@@ -19,10 +19,18 @@ module AutoAssignmentHandler
       AutoAssignment::AssignmentJob.perform_later(inbox_id: inbox.id)
     else
       # Use legacy assignment system
-      AutoAssignment::AgentAssignmentService.new(conversation: self, allowed_agent_ids: inbox.member_ids_with_assignment_capacity).perform
+      # If conversation has a team, only consider team members for assignment
+      allowed_agent_ids = team_id.present? ? team_member_ids_with_capacity : inbox.member_ids_with_assignment_capacity
+      AutoAssignment::AgentAssignmentService.new(conversation: self, allowed_agent_ids: allowed_agent_ids).perform
     end
   end
 
+  def team_member_ids_with_capacity
+    return [] if team.blank? || team.allow_auto_assign.blank?
+
+    inbox.member_ids_with_assignment_capacity & team.members.ids
+  end
+
   def should_run_auto_assignment?
     return false unless inbox.enable_auto_assignment?
 
diff --git a/app/services/auto_assignment/assignment_service.rb b/app/services/auto_assignment/assignment_service.rb
index 5d75c515f..89eff9d1c 100644
--- a/app/services/auto_assignment/assignment_service.rb
+++ b/app/services/auto_assignment/assignment_service.rb
@@ -19,7 +19,7 @@ class AutoAssignment::AssignmentService
   def perform_for_conversation(conversation)
     return false unless assignable?(conversation)
 
-    agent = find_available_agent
+    agent = find_available_agent(conversation)
     return false unless agent
 
     assign_conversation(conversation, agent)
@@ -44,13 +44,26 @@ class AutoAssignment::AssignmentService
     scope.limit(limit)
   end
 
-  def find_available_agent
-    agents = filter_agents_by_rate_limit(inbox.available_agents)
+  def find_available_agent(conversation = nil)
+    agents = filter_agents_by_team(inbox.available_agents, conversation)
+    return nil if agents.nil?
+
+    agents = filter_agents_by_rate_limit(agents)
     return nil if agents.empty?
 
     round_robin_selector.select_agent(agents)
   end
 
+  def filter_agents_by_team(agents, conversation)
+    return agents if conversation&.team_id.blank?
+
+    team = conversation.team
+    return nil if team.blank? || team.allow_auto_assign.blank?
+
+    team_member_ids = team.members.ids
+    agents.where(user_id: team_member_ids)
+  end
+
   def filter_agents_by_rate_limit(agents)
     agents.select do |agent_member|
       rate_limiter = build_rate_limiter(agent_member.user)
diff --git a/app/services/twilio/delivery_status_service.rb b/app/services/twilio/delivery_status_service.rb
index bf8422fcd..bed390aa5 100644
--- a/app/services/twilio/delivery_status_service.rb
+++ b/app/services/twilio/delivery_status_service.rb
@@ -47,8 +47,10 @@ class Twilio::DeliveryStatusService
     @twilio_channel ||= if params[:MessagingServiceSid].present?
                           ::Channel::TwilioSms.find_by(messaging_service_sid: params[:MessagingServiceSid])
                         elsif params[:AccountSid].present? && params[:From].present?
-                          ::Channel::TwilioSms.find_by!(account_sid: params[:AccountSid], phone_number: params[:From])
+                          ::Channel::TwilioSms.find_by(account_sid: params[:AccountSid], phone_number: params[:From])
                         end
+    log_channel_not_found if @twilio_channel.blank?
+    @twilio_channel
   end
 
   def message
@@ -56,4 +58,14 @@ class Twilio::DeliveryStatusService
 
     @message ||= twilio_channel.inbox.messages.find_by(source_id: params[:MessageSid])
   end
+
+  def log_channel_not_found
+    Rails.logger.warn(
+      '[TWILIO] Delivery status channel lookup failed ' \
+      "account_sid=#{params[:AccountSid]} " \
+      "from=#{params[:From]} " \
+      "messaging_service_sid=#{params[:MessagingServiceSid]} " \
+      "message_sid=#{params[:MessageSid]}"
+    )
+  end
 end
diff --git a/app/services/twilio/incoming_message_service.rb b/app/services/twilio/incoming_message_service.rb
index 5d695ebb2..d67b6d515 100644
--- a/app/services/twilio/incoming_message_service.rb
+++ b/app/services/twilio/incoming_message_service.rb
@@ -26,12 +26,23 @@ class Twilio::IncomingMessageService
   def twilio_channel
     @twilio_channel ||= ::Channel::TwilioSms.find_by(messaging_service_sid: params[:MessagingServiceSid]) if params[:MessagingServiceSid].present?
     if params[:AccountSid].present? && params[:To].present?
-      @twilio_channel ||= ::Channel::TwilioSms.find_by!(account_sid: params[:AccountSid],
-                                                        phone_number: params[:To])
+      @twilio_channel ||= ::Channel::TwilioSms.find_by(account_sid: params[:AccountSid],
+                                                       phone_number: params[:To])
     end
+    log_channel_not_found if @twilio_channel.blank?
     @twilio_channel
   end
 
+  def log_channel_not_found
+    Rails.logger.warn(
+      '[TWILIO] Incoming message channel lookup failed ' \
+      "account_sid=#{params[:AccountSid]} " \
+      "to=#{params[:To]} " \
+      "messaging_service_sid=#{params[:MessagingServiceSid]} " \
+      "sms_sid=#{params[:SmsSid]}"
+    )
+  end
+
   def inbox
     @inbox ||= twilio_channel.inbox
   end
diff --git a/app/services/whatsapp/incoming_message_base_service.rb b/app/services/whatsapp/incoming_message_base_service.rb
index a90814bdc..a8ad176b6 100644
--- a/app/services/whatsapp/incoming_message_base_service.rb
+++ b/app/services/whatsapp/incoming_message_base_service.rb
@@ -28,19 +28,19 @@ class Whatsapp::IncomingMessageBaseService
     # if the webhook event is a reaction or an ephermal message or an unsupported message.
     return if unprocessable_message_type?(message_type)
 
-    # Multiple webhook event can be received against the same message due to misconfigurations in the Meta
-    # business manager account. While we have not found the core reason yet, the following line ensure that
-    # there are no duplicate messages created.
-    return if find_message_by_source_id(messages_data.first[:id]) || message_under_process?
+    # Multiple webhook events can be received for the same message due to
+    # misconfigurations in the Meta business manager account.
+    # We use an atomic Redis SET NX to prevent concurrent workers from both
+    # processing the same message simultaneously.
+    return if find_message_by_source_id(messages_data.first[:id])
+    return unless lock_message_source_id!
 
-    cache_message_source_id_in_redis
     set_contact
     return unless @contact
 
     ActiveRecord::Base.transaction do
       set_conversation
       create_messages
-      clear_message_source_id_from_redis
     end
   end
 
diff --git a/app/services/whatsapp/incoming_message_service_helpers.rb b/app/services/whatsapp/incoming_message_service_helpers.rb
index c803d61bd..bac6f6222 100644
--- a/app/services/whatsapp/incoming_message_service_helpers.rb
+++ b/app/services/whatsapp/incoming_message_service_helpers.rb
@@ -69,20 +69,9 @@ module Whatsapp::IncomingMessageServiceHelpers
     @message = Message.find_by(source_id: source_id)
   end
 
-  def message_under_process?
-    key = format(Redis::RedisKeys::MESSAGE_SOURCE_KEY, id: messages_data.first[:id])
-    Redis::Alfred.get(key)
-  end
+  def lock_message_source_id!
+    return false if messages_data.blank?
 
-  def cache_message_source_id_in_redis
-    return if messages_data.blank?
-
-    key = format(Redis::RedisKeys::MESSAGE_SOURCE_KEY, id: messages_data.first[:id])
-    ::Redis::Alfred.setex(key, true)
-  end
-
-  def clear_message_source_id_from_redis
-    key = format(Redis::RedisKeys::MESSAGE_SOURCE_KEY, id: messages_data.first[:id])
-    ::Redis::Alfred.delete(key)
+    Whatsapp::MessageDedupLock.new(messages_data.first[:id]).acquire!
   end
 end
diff --git a/app/services/whatsapp/message_dedup_lock.rb b/app/services/whatsapp/message_dedup_lock.rb
new file mode 100644
index 000000000..4a863a4a4
--- /dev/null
+++ b/app/services/whatsapp/message_dedup_lock.rb
@@ -0,0 +1,19 @@
+# Atomic dedup lock for WhatsApp incoming messages.
+#
+# Meta can deliver the same webhook event multiple times. This lock uses
+# Redis SET NX EX to ensure only one worker processes a given source_id.
+class Whatsapp::MessageDedupLock
+  KEY_PREFIX = Redis::RedisKeys::MESSAGE_SOURCE_KEY
+  DEFAULT_TTL = 1.day.to_i
+
+  def initialize(source_id, ttl: DEFAULT_TTL)
+    @key = format(KEY_PREFIX, id: source_id)
+    @ttl = ttl
+  end
+
+  # Returns true when the lock is acquired (caller should proceed).
+  # Returns false when another worker already holds the lock.
+  def acquire!
+    ::Redis::Alfred.set(@key, true, nx: true, ex: @ttl)
+  end
+end
diff --git a/config/locales/en.yml b/config/locales/en.yml
index f8d5b119e..07d9b0e2f 100644
--- a/config/locales/en.yml
+++ b/config/locales/en.yml
@@ -41,8 +41,7 @@ en:
       invalid_email: 'Please enter a valid email address'
       authentication_failed: 'Authentication failed. Please check your credentials and try again.'
   messages:
-    reset_password_success: Woot! Request for password reset is successful. Check your mail for instructions.
-    reset_password_failure: Uh ho! We could not find any user with the specified email.
+    reset_password: Request for password reset is successful. A email with instructions will be sent to your email if it exists.
     reset_password_saml_user: This account uses SAML authentication. Password reset is not available. Please contact your administrator.
     login_saml_user: This account uses SAML authentication. Please sign in through your organization's SAML provider.
     saml_not_available: SAML authentication is not available in this installation.
diff --git a/enterprise/app/helpers/captain/chat_response_helper.rb b/enterprise/app/helpers/captain/chat_response_helper.rb
index e0323996f..bfb8adc11 100644
--- a/enterprise/app/helpers/captain/chat_response_helper.rb
+++ b/enterprise/app/helpers/captain/chat_response_helper.rb
@@ -1,10 +1,13 @@
 module Captain::ChatResponseHelper
+  include Integrations::LlmInstrumentationConstants
+
   private
 
   def build_response(response)
     Rails.logger.debug { "#{self.class.name} Assistant: #{@assistant.id}, Received response #{response}" }
 
     parsed = parse_json_response(response.content)
+    apply_credit_usage_metadata(parsed)
 
     persist_message(parsed, 'assistant')
     parsed
@@ -19,6 +22,26 @@ module Captain::ChatResponseHelper
     { 'content' => content }
   end
 
+  def apply_credit_usage_metadata(parsed_response)
+    return unless captain_v1_assistant?
+
+    OpenTelemetry::Trace.current_span.set_attribute(
+      format(ATTR_LANGFUSE_METADATA, 'credit_used'),
+      credit_used_for_response?(parsed_response).to_s
+    )
+  rescue StandardError => e
+    Rails.logger.warn "#{self.class.name} Assistant: #{@assistant.id}, Failed to set credit usage metadata: #{e.message}"
+  end
+
+  def credit_used_for_response?(parsed_response)
+    response = parsed_response['response']
+    response.present? && response != 'conversation_handoff'
+  end
+
+  def captain_v1_assistant?
+    feature_name == 'assistant' && !@assistant.account.feature_enabled?('captain_integration_v2')
+  end
+
   def persist_thinking_message(tool_call)
     return if @copilot_thread.blank?
 
diff --git a/enterprise/app/jobs/messages/audio_transcription_job.rb b/enterprise/app/jobs/messages/audio_transcription_job.rb
index ce35405c8..5daf1e160 100644
--- a/enterprise/app/jobs/messages/audio_transcription_job.rb
+++ b/enterprise/app/jobs/messages/audio_transcription_job.rb
@@ -1,6 +1,15 @@
 class Messages::AudioTranscriptionJob < ApplicationJob
   queue_as :low
 
+  discard_on Faraday::BadRequestError do |job, error|
+    log_context = {
+      attachment_id: job.arguments.first,
+      job_id: job.job_id,
+      status_code: error.response&.dig(:status)
+    }
+
+    Rails.logger.warn("Discarding audio transcription job due to bad request: #{log_context}")
+  end
   retry_on ActiveStorage::FileNotFoundError, wait: 2.seconds, attempts: 3
 
   def perform(attachment_id)
diff --git a/enterprise/app/services/captain/assistant/agent_runner_service.rb b/enterprise/app/services/captain/assistant/agent_runner_service.rb
index 9c4e56841..a40e096e6 100644
--- a/enterprise/app/services/captain/assistant/agent_runner_service.rb
+++ b/enterprise/app/services/captain/assistant/agent_runner_service.rb
@@ -1,6 +1,9 @@
 require 'agents'
+require 'agents/instrumentation'
 
 class Captain::Assistant::AgentRunnerService
+  include Integrations::LlmInstrumentationConstants
+
   CONVERSATION_STATE_ATTRIBUTES = %i[
     id display_id inbox_id contact_id status priority
     label_list custom_attributes additional_attributes
@@ -22,7 +25,9 @@ class Captain::Assistant::AgentRunnerService
     context = build_context(message_history)
     message_to_process = extract_last_user_message(message_history)
     runner = Agents::Runner.with_agents(*agents)
+    runner = add_usage_metadata_callback(runner)
     runner = add_callbacks_to_runner(runner) if @callbacks.any?
+    install_instrumentation(runner)
     result = runner.run(message_to_process, context: context, max_turns: 100)
 
     process_agent_result(result)
@@ -50,6 +55,7 @@ class Captain::Assistant::AgentRunnerService
     end
 
     {
+      session_id: "#{@assistant.account_id}_#{@conversation&.display_id}",
       conversation_history: conversation_history,
       state: build_state
     }
@@ -124,6 +130,31 @@ class Captain::Assistant::AgentRunnerService
     [assistant_agent] + scenario_agents
   end
 
+  def install_instrumentation(runner)
+    return unless ChatwootApp.otel_enabled?
+
+    Agents::Instrumentation.install(
+      runner,
+      tracer: OpentelemetryConfig.tracer,
+      trace_name: 'llm.captain_v2',
+      span_attributes: {
+        ATTR_LANGFUSE_TAGS => ['captain_v2'].to_json
+      },
+      attribute_provider: ->(context_wrapper) { dynamic_trace_attributes(context_wrapper) }
+    )
+  end
+
+  def dynamic_trace_attributes(context_wrapper)
+    state = context_wrapper&.context&.dig(:state) || {}
+    conversation = state[:conversation] || {}
+    {
+      ATTR_LANGFUSE_USER_ID => state[:account_id],
+      format(ATTR_LANGFUSE_METADATA, 'assistant_id') => state[:assistant_id],
+      format(ATTR_LANGFUSE_METADATA, 'conversation_id') => conversation[:id],
+      format(ATTR_LANGFUSE_METADATA, 'conversation_display_id') => conversation[:display_id]
+    }.compact.transform_values(&:to_s)
+  end
+
   def add_callbacks_to_runner(runner)
     runner = add_agent_thinking_callback(runner) if @callbacks[:on_agent_thinking]
     runner = add_tool_start_callback(runner) if @callbacks[:on_tool_start]
@@ -132,6 +163,36 @@ class Captain::Assistant::AgentRunnerService
     runner
   end
 
+  def add_usage_metadata_callback(runner)
+    return runner unless ChatwootApp.otel_enabled?
+
+    handoff_tool_name = Captain::Tools::HandoffTool.new(@assistant).name
+
+    runner.on_tool_complete do |tool_name, _tool_result, context_wrapper|
+      track_handoff_usage(tool_name, handoff_tool_name, context_wrapper)
+    end
+
+    runner.on_run_complete do |_agent_name, _result, context_wrapper|
+      write_credits_used_metadata(context_wrapper)
+    end
+    runner
+  end
+
+  def track_handoff_usage(tool_name, handoff_tool_name, context_wrapper)
+    return unless context_wrapper&.context
+    return unless tool_name.to_s == handoff_tool_name
+
+    context_wrapper.context[:captain_v2_handoff_tool_called] = true
+  end
+
+  def write_credits_used_metadata(context_wrapper)
+    root_span = context_wrapper&.context&.dig(:__otel_tracing, :root_span)
+    return unless root_span
+
+    credits_used = !context_wrapper.context[:captain_v2_handoff_tool_called]
+    root_span.set_attribute(format(ATTR_LANGFUSE_METADATA, 'credits_used'), credits_used)
+  end
+
   def add_agent_thinking_callback(runner)
     runner.on_agent_thinking do |*args|
       @callbacks[:on_agent_thinking].call(*args)
diff --git a/enterprise/app/services/enterprise/auto_assignment/assignment_service.rb b/enterprise/app/services/enterprise/auto_assignment/assignment_service.rb
index 46422f9bc..66cdc31e5 100644
--- a/enterprise/app/services/enterprise/auto_assignment/assignment_service.rb
+++ b/enterprise/app/services/enterprise/auto_assignment/assignment_service.rb
@@ -14,8 +14,11 @@ module Enterprise::AutoAssignment::AssignmentService
   end
 
   # Extend agent finding to add capacity checks
-  def find_available_agent
-    agents = filter_agents_by_rate_limit(inbox.available_agents)
+  def find_available_agent(conversation = nil)
+    agents = filter_agents_by_team(inbox.available_agents, conversation)
+    return nil if agents.nil?
+
+    agents = filter_agents_by_rate_limit(agents)
     agents = filter_agents_by_capacity(agents) if capacity_filtering_enabled?
     return nil if agents.empty?
 
diff --git a/enterprise/app/services/messages/audio_transcription_service.rb b/enterprise/app/services/messages/audio_transcription_service.rb
index 1676dd862..4aa156f47 100644
--- a/enterprise/app/services/messages/audio_transcription_service.rb
+++ b/enterprise/app/services/messages/audio_transcription_service.rb
@@ -31,12 +31,20 @@ class Messages::AudioTranscriptionService< Llm::LegacyBaseOpenAiService
   end
 
   def fetch_audio_file
+    blob = attachment.file.blob
     temp_dir = Rails.root.join('tmp/uploads/audio-transcriptions')
     FileUtils.mkdir_p(temp_dir)
-    temp_file_path = File.join(temp_dir, "#{attachment.file.blob.key}-#{attachment.file.filename}")
+    temp_file_name = "#{blob.key}-#{blob.filename}"
+
+    if blob.filename.extension_without_delimiter.blank?
+      extension = extension_from_content_type(blob.content_type)
+      temp_file_name = "#{temp_file_name}.#{extension}" if extension.present?
+    end
+
+    temp_file_path = File.join(temp_dir, temp_file_name)
 
     File.open(temp_file_path, 'wb') do |file|
-      attachment.file.blob.open do |blob_file|
+      blob.open do |blob_file|
         IO.copy_stream(blob_file, file)
       end
     end
@@ -49,13 +57,12 @@ class Messages::AudioTranscriptionService< Llm::LegacyBaseOpenAiService
     return transcribed_text if transcribed_text.present?
 
     temp_file_path = fetch_audio_file
-
     transcribed_text = nil
 
     File.open(temp_file_path, 'rb') do |file|
       response = @client.audio.transcribe(
         parameters: {
-          model: 'whisper-1',
+          model: WHISPER_MODEL,
           file: file,
           temperature: 0.4
         }
@@ -63,10 +70,10 @@ class Messages::AudioTranscriptionService< Llm::LegacyBaseOpenAiService
       transcribed_text = response['text']
     end
 
-    FileUtils.rm_f(temp_file_path)
-
     update_transcription(transcribed_text)
     transcribed_text
+  ensure
+    FileUtils.rm_f(temp_file_path) if temp_file_path.present?
   end
 
   def instrumentation_params(file_path)
@@ -90,4 +97,15 @@ class Messages::AudioTranscriptionService< Llm::LegacyBaseOpenAiService
 
     message.reindex
   end
+
+  def extension_from_content_type(content_type)
+    subtype = content_type.to_s.downcase.split(';').first.to_s.split('/').last.to_s
+    return if subtype.blank?
+
+    {
+      'x-m4a' => 'm4a',
+      'x-wav' => 'wav',
+      'x-mp3' => 'mp3'
+    }.fetch(subtype, subtype)
+  end
 end
diff --git a/lib/captain/tool_instrumentation.rb b/lib/captain/tool_instrumentation.rb
index af79a3fca..157aab829 100644
--- a/lib/captain/tool_instrumentation.rb
+++ b/lib/captain/tool_instrumentation.rb
@@ -15,6 +15,7 @@ module Captain::ToolInstrumentation
       response = yield
       executed = true
       span.set_attribute(ATTR_LANGFUSE_OBSERVATION_OUTPUT, response[:message] || response.to_json)
+      set_tool_session_error_attributes(span, response) if response.is_a?(Hash)
     end
     response
   rescue StandardError => e
@@ -29,6 +30,14 @@ module Captain::ToolInstrumentation
     span.set_attribute(ATTR_LANGFUSE_OBSERVATION_INPUT, params[:messages].to_json)
   end
 
+  def set_tool_session_error_attributes(span, response)
+    error = response[:error] || response['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 record_generation(chat, message, model)
     return unless ChatwootApp.otel_enabled?
     return unless message.respond_to?(:role) && message.role.to_s == 'assistant'
diff --git a/lib/integrations/llm_instrumentation.rb b/lib/integrations/llm_instrumentation.rb
index c3baf291e..326bb901e 100644
--- a/lib/integrations/llm_instrumentation.rb
+++ b/lib/integrations/llm_instrumentation.rb
@@ -37,6 +37,7 @@ module Integrations::LlmInstrumentation
       result = yield
       executed = true
       span.set_attribute(ATTR_LANGFUSE_OBSERVATION_OUTPUT, result.to_json)
+      set_error_attributes(span, result) if result.is_a?(Hash)
       result
     end
   rescue StandardError => e
@@ -50,9 +51,11 @@ module Integrations::LlmInstrumentation
     return yield unless ChatwootApp.otel_enabled?
 
     tracer.in_span(format(TOOL_SPAN_NAME, tool_name)) do |span|
+      span.set_attribute(ATTR_LANGFUSE_OBSERVATION_TYPE, 'tool')
       span.set_attribute(ATTR_LANGFUSE_OBSERVATION_INPUT, arguments.to_json)
       result = yield
       span.set_attribute(ATTR_LANGFUSE_OBSERVATION_OUTPUT, result.to_json)
+      set_error_attributes(span, result) if result.is_a?(Hash)
       result
     end
   end
diff --git a/lib/integrations/llm_instrumentation_constants.rb b/lib/integrations/llm_instrumentation_constants.rb
index 6ce296ee9..dfe1e7704 100644
--- a/lib/integrations/llm_instrumentation_constants.rb
+++ b/lib/integrations/llm_instrumentation_constants.rb
@@ -26,6 +26,7 @@ module Integrations::LlmInstrumentationConstants
   ATTR_LANGFUSE_METADATA = 'langfuse.trace.metadata.%s'
   ATTR_LANGFUSE_TRACE_INPUT = 'langfuse.trace.input'
   ATTR_LANGFUSE_TRACE_OUTPUT = 'langfuse.trace.output'
+  ATTR_LANGFUSE_OBSERVATION_TYPE = 'langfuse.observation.type'
   ATTR_LANGFUSE_OBSERVATION_INPUT = 'langfuse.observation.input'
   ATTR_LANGFUSE_OBSERVATION_OUTPUT = 'langfuse.observation.output'
 end
diff --git a/lib/integrations/llm_instrumentation_spans.rb b/lib/integrations/llm_instrumentation_spans.rb
index 824b6aa4a..85ea599f8 100644
--- a/lib/integrations/llm_instrumentation_spans.rb
+++ b/lib/integrations/llm_instrumentation_spans.rb
@@ -39,6 +39,7 @@ module Integrations::LlmInstrumentationSpans
 
     tool_name = tool_call.name.to_s
     span = tracer.start_span(format(TOOL_SPAN_NAME, tool_name))
+    span.set_attribute(ATTR_LANGFUSE_OBSERVATION_TYPE, 'tool')
     span.set_attribute(ATTR_LANGFUSE_OBSERVATION_INPUT, tool_call.arguments.to_json)
 
     @pending_tool_spans ||= []
diff --git a/spec/controllers/api/v1/accounts/conversations_controller_spec.rb b/spec/controllers/api/v1/accounts/conversations_controller_spec.rb
index 3c380c155..bc7b4097f 100644
--- a/spec/controllers/api/v1/accounts/conversations_controller_spec.rb
+++ b/spec/controllers/api/v1/accounts/conversations_controller_spec.rb
@@ -330,6 +330,7 @@ RSpec.describe 'Conversations API', type: :request do
       context 'when it is an authenticated user who has access to the inbox' do
         before do
           create(:inbox_member, user: agent, inbox: inbox)
+          create(:team_member, user: agent, team: team)
         end
 
         it 'creates a new conversation' do
diff --git a/spec/enterprise/services/captain/assistant/agent_runner_service_spec.rb b/spec/enterprise/services/captain/assistant/agent_runner_service_spec.rb
index 2c05860e2..04fa0f967 100644
--- a/spec/enterprise/services/captain/assistant/agent_runner_service_spec.rb
+++ b/spec/enterprise/services/captain/assistant/agent_runner_service_spec.rb
@@ -75,6 +75,7 @@ RSpec.describe Captain::Assistant::AgentRunnerService do
 
     it 'runs agent with extracted user message and context' do
       expected_context = {
+        session_id: "#{account.id}_#{conversation.display_id}",
         conversation_history: [
           { role: :user, content: 'Hello there', agent_name: nil },
           { role: :assistant, content: 'Hi! How can I help you?', agent_name: 'Assistant' },
@@ -306,6 +307,60 @@ RSpec.describe Captain::Assistant::AgentRunnerService do
     end
   end
 
+  describe '#add_usage_metadata_callback' do
+    it 'sets credits_used=false when handoff tool is used' do
+      service = described_class.new(assistant: assistant, conversation: conversation)
+      runner = instance_double(Agents::AgentRunner)
+      tool_complete_callback = nil
+      run_complete_callback = nil
+      span_class = Class.new do
+        def set_attribute(*); end
+      end
+      root_span = instance_double(span_class)
+      context_wrapper = Struct.new(:context).new({ __otel_tracing: { root_span: root_span } })
+
+      allow(ChatwootApp).to receive(:otel_enabled?).and_return(true)
+      allow(runner).to receive(:on_tool_complete) do |&block|
+        tool_complete_callback = block
+        runner
+      end
+      allow(runner).to receive(:on_run_complete) do |&block|
+        run_complete_callback = block
+        runner
+      end
+
+      service.send(:add_usage_metadata_callback, runner)
+
+      tool_complete_callback.call(Captain::Tools::HandoffTool.new(assistant).name, 'ok', context_wrapper)
+
+      expect(root_span).to receive(:set_attribute).with('langfuse.trace.metadata.credits_used', false)
+      run_complete_callback.call('assistant', nil, context_wrapper)
+    end
+
+    it 'sets credits_used=true when handoff tool is not used' do
+      service = described_class.new(assistant: assistant, conversation: conversation)
+      runner = instance_double(Agents::AgentRunner)
+      run_complete_callback = nil
+      span_class = Class.new do
+        def set_attribute(*); end
+      end
+      root_span = instance_double(span_class)
+      context_wrapper = Struct.new(:context).new({ __otel_tracing: { root_span: root_span } })
+
+      allow(ChatwootApp).to receive(:otel_enabled?).and_return(true)
+      allow(runner).to receive(:on_tool_complete).and_return(runner)
+      allow(runner).to receive(:on_run_complete) do |&block|
+        run_complete_callback = block
+        runner
+      end
+
+      service.send(:add_usage_metadata_callback, runner)
+
+      expect(root_span).to receive(:set_attribute).with('langfuse.trace.metadata.credits_used', true)
+      run_complete_callback.call('assistant', nil, context_wrapper)
+    end
+  end
+
   describe 'constants' do
     it 'defines conversation state attributes' do
       expect(described_class::CONVERSATION_STATE_ATTRIBUTES).to include(
diff --git a/spec/enterprise/services/messages/audio_transcription_service_spec.rb b/spec/enterprise/services/messages/audio_transcription_service_spec.rb
index 41a4cae83..7ece2540a 100644
--- a/spec/enterprise/services/messages/audio_transcription_service_spec.rb
+++ b/spec/enterprise/services/messages/audio_transcription_service_spec.rb
@@ -8,8 +8,8 @@ RSpec.describe Messages::AudioTranscriptionService, type: :service do
 
   before do
     # Create required installation configs
-    create(:installation_config, name: 'CAPTAIN_OPEN_AI_API_KEY', value: 'test-api-key')
-    create(:installation_config, name: 'CAPTAIN_OPEN_AI_MODEL', value: 'gpt-4o-mini')
+    InstallationConfig.find_or_create_by!(name: 'CAPTAIN_OPEN_AI_API_KEY') { |config| config.value = 'test-api-key' }
+    InstallationConfig.find_or_create_by!(name: 'CAPTAIN_OPEN_AI_MODEL') { |config| config.value = 'gpt-4o-mini' }
 
     # Mock usage limits for transcription to be available
     allow(account).to receive(:usage_limits).and_return({ captain: { responses: { current_available: 100 } } })
@@ -64,4 +64,24 @@ RSpec.describe Messages::AudioTranscriptionService, type: :service do
       end
     end
   end
+
+  describe '#fetch_audio_file' do
+    let(:service) { described_class.new(attachment) }
+
+    before do
+      attachment.file.attach(
+        io: File.open(Rails.public_path.join('audio/widget/ding.mp3')),
+        filename: 'speech',
+        content_type: 'audio/mpeg'
+      )
+    end
+
+    it 'adds extension from content type when filename has no extension' do
+      temp_file_path = service.send(:fetch_audio_file)
+
+      expect(File.extname(temp_file_path)).to eq('.mpeg')
+    ensure
+      FileUtils.rm_f(temp_file_path) if temp_file_path.present?
+    end
+  end
 end
diff --git a/spec/services/auto_assignment/assignment_service_spec.rb b/spec/services/auto_assignment/assignment_service_spec.rb
index 2139e5e78..36a8c7816 100644
--- a/spec/services/auto_assignment/assignment_service_spec.rb
+++ b/spec/services/auto_assignment/assignment_service_spec.rb
@@ -307,5 +307,52 @@ RSpec.describe AutoAssignment::AssignmentService do
         end
       end
     end
+
+    context 'with team assignments' do
+      let(:team) { create(:team, account: account, allow_auto_assign: true) }
+      let(:team_member) { create(:user, account: account, role: :agent, availability: :online) }
+      let(:rate_limiter) { instance_double(AutoAssignment::RateLimiter) }
+
+      before do
+        create(:team_member, team: team, user: team_member)
+        create(:inbox_member, inbox: inbox, user: team_member)
+
+        allow(OnlineStatusTracker).to receive(:get_available_users).and_return({ team_member.id.to_s => 'online' })
+
+        allow(AutoAssignment::RateLimiter).to receive(:new).and_return(rate_limiter)
+        allow(rate_limiter).to receive(:within_limit?).and_return(true)
+        allow(rate_limiter).to receive(:track_assignment)
+
+        round_robin_selector = instance_double(AutoAssignment::RoundRobinSelector)
+        allow(AutoAssignment::RoundRobinSelector).to receive(:new).and_return(round_robin_selector)
+        allow(round_robin_selector).to receive(:select_agent).and_return(team_member)
+      end
+
+      it 'assigns conversation with team to team member' do
+        conversation_with_team = create(:conversation, inbox: inbox, team: team, assignee: nil)
+
+        service.perform_bulk_assignment(limit: 1)
+
+        expect(conversation_with_team.reload.assignee).to eq(team_member)
+      end
+
+      it 'skips assignment when team has allow_auto_assign false' do
+        team.update!(allow_auto_assign: false)
+        conversation_with_team = create(:conversation, inbox: inbox, team: team, assignee: nil)
+
+        service.perform_bulk_assignment(limit: 1)
+
+        expect(conversation_with_team.reload.assignee).to be_nil
+      end
+
+      it 'skips assignment when no team members are available' do
+        allow(OnlineStatusTracker).to receive(:get_available_users).and_return({})
+        conversation_with_team = create(:conversation, inbox: inbox, team: team, assignee: nil)
+
+        service.perform_bulk_assignment(limit: 1)
+
+        expect(conversation_with_team.reload.assignee).to be_nil
+      end
+    end
   end
 end
diff --git a/spec/services/whatsapp/incoming_message_service_spec.rb b/spec/services/whatsapp/incoming_message_service_spec.rb
index 6c23e9b71..2ecf60acb 100644
--- a/spec/services/whatsapp/incoming_message_service_spec.rb
+++ b/spec/services/whatsapp/incoming_message_service_spec.rb
@@ -6,6 +6,14 @@ describe Whatsapp::IncomingMessageService do
       stub_request(:post, 'https://waba.360dialog.io/v1/configs/webhook')
     end
 
+    after do
+      # The atomic dedup lock lives in Redis and is not rolled back by
+      # transactional fixtures. Clean up any keys created during the test.
+      Redis::Alfred.scan_each(match: 'MESSAGE_SOURCE_KEY::*') do |key|
+        Redis::Alfred.delete(key)
+      end
+    end
+
     let!(:whatsapp_channel) { create(:channel_whatsapp, sync_templates: false) }
     let(:wa_id) { '2423423243' }
     let!(:params) do
@@ -393,8 +401,8 @@ describe Whatsapp::IncomingMessageService do
       end
     end
 
-    describe 'when message processing is in progress' do
-      it 'ignores the current message creation request' do
+    describe 'when another worker already holds the dedup lock' do
+      it 'skips message creation' do
         params = { 'contacts' => [{ 'profile' => { 'name' => 'Kedar' }, 'wa_id' => '919746334593' }],
                    'messages' => [{ 'from' => '919446284490',
                                     'id' => 'wamid.SDFADSf23sfasdafasdfa',
@@ -409,17 +417,14 @@ describe Whatsapp::IncomingMessageService do
                                         'phones' => [{ 'phone' => '+1 (415) 341-8386' }] }
                                     ] }] }.with_indifferent_access
 
-        expect(Message.find_by(source_id: 'wamid.SDFADSf23sfasdafasdfa')).not_to be_present
-        key = format(Redis::RedisKeys::MESSAGE_SOURCE_KEY, id: 'wamid.SDFADSf23sfasdafasdfa')
-
-        Redis::Alfred.setex(key, true)
-        expect(Redis::Alfred.get(key)).to be_truthy
+        # Simulate another worker holding the lock
+        lock = Whatsapp::MessageDedupLock.new('wamid.SDFADSf23sfasdafasdfa')
+        expect(lock.acquire!).to be_truthy
 
         described_class.new(inbox: whatsapp_channel.inbox, params: params).perform
         expect(whatsapp_channel.inbox.messages.count).to eq(0)
-        expect(Message.find_by(source_id: 'wamid.SDFADSf23sfasdafasdfa')).not_to be_present
-
-        expect(Redis::Alfred.get(key)).to be_truthy
+      ensure
+        key = format(Redis::RedisKeys::MESSAGE_SOURCE_KEY, id: 'wamid.SDFADSf23sfasdafasdfa')
         Redis::Alfred.delete(key)
       end
     end
diff --git a/spec/services/whatsapp/incoming_message_whatsapp_cloud_service_spec.rb b/spec/services/whatsapp/incoming_message_whatsapp_cloud_service_spec.rb
index 6112ddc7b..4b6841811 100644
--- a/spec/services/whatsapp/incoming_message_whatsapp_cloud_service_spec.rb
+++ b/spec/services/whatsapp/incoming_message_whatsapp_cloud_service_spec.rb
@@ -2,6 +2,10 @@ require 'rails_helper'
 
 describe Whatsapp::IncomingMessageWhatsappCloudService do
   describe '#perform' do
+    after do
+      Redis::Alfred.scan_each(match: 'MESSAGE_SOURCE_KEY::*') { |key| Redis::Alfred.delete(key) }
+    end
+
     let!(:whatsapp_channel) { create(:channel_whatsapp, provider: 'whatsapp_cloud', sync_templates: false, validate_provider_config: false) }
     let(:params) do
       {
diff --git a/spec/services/whatsapp/message_dedup_lock_spec.rb b/spec/services/whatsapp/message_dedup_lock_spec.rb
new file mode 100644
index 000000000..f3009b2ff
--- /dev/null
+++ b/spec/services/whatsapp/message_dedup_lock_spec.rb
@@ -0,0 +1,43 @@
+require 'rails_helper'
+
+describe Whatsapp::MessageDedupLock do
+  let(:source_id) { "wamid.test_#{SecureRandom.hex(8)}" }
+  let(:lock) { described_class.new(source_id) }
+  let(:redis_key) { format(Redis::RedisKeys::MESSAGE_SOURCE_KEY, id: source_id) }
+
+  after { Redis::Alfred.delete(redis_key) }
+
+  describe '#acquire!' do
+    it 'returns truthy on first acquire' do
+      expect(lock.acquire!).to be_truthy
+    end
+
+    it 'returns falsy on second acquire for the same source_id' do
+      lock.acquire!
+      expect(described_class.new(source_id).acquire!).to be_falsy
+    end
+
+    it 'allows different source_ids to acquire independently' do
+      lock.acquire!
+      other = described_class.new("wamid.other_#{SecureRandom.hex(8)}")
+      expect(other.acquire!).to be_truthy
+    end
+
+    it 'lets exactly one thread win when two race for the same source_id' do
+      results = Concurrent::Array.new
+      barrier = Concurrent::CyclicBarrier.new(2)
+
+      threads = Array.new(2) do
+        Thread.new do
+          barrier.wait
+          results << described_class.new(source_id).acquire!
+        end
+      end
+
+      threads.each(&:join)
+
+      wins = results.count { |r| r }
+      expect(wins).to eq(1), "Expected exactly 1 winner but got #{wins}. Results: #{results.inspect}"
+    end
+  end
+end