diff --git a/app/controllers/api/v1/accounts/microsoft/authorizations_controller.rb b/app/controllers/api/v1/accounts/microsoft/authorizations_controller.rb
index a300b5f59..c65a3031d 100644
--- a/app/controllers/api/v1/accounts/microsoft/authorizations_controller.rb
+++ b/app/controllers/api/v1/accounts/microsoft/authorizations_controller.rb
@@ -6,8 +6,7 @@ class Api::V1::Accounts::Microsoft::AuthorizationsController < Api::V1::Accounts
       {
         redirect_uri: "#{base_url}/microsoft/callback",
         scope: scope,
-        state: state,
-        prompt: 'consent'
+        state: state
       }
     )
     if redirect_url
diff --git a/app/helpers/super_admin/features.yml b/app/helpers/super_admin/features.yml
index f21a97f78..6489d0194 100644
--- a/app/helpers/super_admin/features.yml
+++ b/app/helpers/super_admin/features.yml
@@ -34,6 +34,12 @@ disable_branding:
   enabled: <%= (ChatwootHub.pricing_plan != 'community') %>
   icon: 'icon-sailbot-fill'
   enterprise: true
+voice_calls:
+  name: 'Voice Calls'
+  description: 'Enable voice calling capabilities for your agents and customers.'
+  enabled: <%= (ChatwootHub.pricing_plan != 'community') %>
+  icon: 'icon-voice-line'
+  enterprise: true
 
 # ------- Product Features ------- #
 help_center:
diff --git a/app/javascript/dashboard/api/channel/voice/twilioVoiceClient.js b/app/javascript/dashboard/api/channel/voice/twilioVoiceClient.js
index 13f61a16c..14dd56ec9 100644
--- a/app/javascript/dashboard/api/channel/voice/twilioVoiceClient.js
+++ b/app/javascript/dashboard/api/channel/voice/twilioVoiceClient.js
@@ -48,6 +48,12 @@ class TwilioVoiceClient extends EventTarget {
     return !!this.activeConnection;
   }
 
+  setMuted(shouldMute) {
+    if (!this.activeConnection) return false;
+    this.activeConnection.mute(shouldMute);
+    return shouldMute;
+  }
+
   endClientCall() {
     if (this.activeConnection) {
       this.activeConnection.disconnect();
diff --git a/app/javascript/dashboard/components-next/call/CallCard.vue b/app/javascript/dashboard/components-next/call/CallCard.vue
index 207129282..55da3dacf 100644
--- a/app/javascript/dashboard/components-next/call/CallCard.vue
+++ b/app/javascript/dashboard/components-next/call/CallCard.vue
@@ -197,9 +197,9 @@ const channelIcon = computed(() => {
                 ? $t('CONVERSATION.VOICE_WIDGET.END_CALL')
                 : $t('CONVERSATION.VOICE_WIDGET.REJECT_CALL')
             "
-            icon="i-ph-phone-x-bold"
+            icon="i-ph-phone-bold"
             ruby
-            class="!rounded-full rotate-[134deg]"
+            class="!rounded-full rotate-[135deg]"
             @click="isOngoing ? $emit('end') : $emit('reject')"
           />
         </div>
diff --git a/app/javascript/dashboard/components-next/call/FloatingCallWidget.vue b/app/javascript/dashboard/components-next/call/FloatingCallWidget.vue
index 86d9e979c..7758500a0 100644
--- a/app/javascript/dashboard/components-next/call/FloatingCallWidget.vue
+++ b/app/javascript/dashboard/components-next/call/FloatingCallWidget.vue
@@ -4,6 +4,7 @@ import { useRoute, useRouter } from 'vue-router';
 import { useStore } from 'vuex';
 import { useCallSession } from 'dashboard/composables/useCallSession';
 import { setWhatsappCallMuted } from 'dashboard/composables/useWhatsappCallSession';
+import TwilioVoiceClient from 'dashboard/api/channel/voice/twilioVoiceClient';
 import { frontendURL, conversationUrl } from 'dashboard/helper/URLHelper';
 import { VOICE_CALL_PROVIDERS } from 'dashboard/helper/inbox';
 import { VOICE_CALL_DIRECTION } from 'dashboard/components-next/message/constants';
@@ -11,7 +12,7 @@ import WindowVisibilityHelper from 'dashboard/helper/AudioAlerts/WindowVisibilit
 import CallCard from 'dashboard/components-next/call/CallCard.vue';
 import countriesList from 'shared/constants/countries.js';
 
-const RINGTONE_URL = '/audio/dashboard/bell.mp3';
+const RINGTONE_URL = '/audio/dashboard/ringtone.mp3';
 
 const route = useRoute();
 const router = useRouter();
@@ -29,8 +30,8 @@ const {
   formattedCallDuration,
 } = useCallSession();
 
-// Mute is currently WhatsApp-only — Twilio calls are mediated server-side and
-// don't expose a mic track on the browser side.
+// Mute routes by provider: WhatsApp toggles the local mic track, Twilio uses
+// the Voice SDK connection's native mute. Both surface the same button.
 const isMuted = ref(false);
 const isWhatsappActive = computed(
   () => activeCall.value?.provider === VOICE_CALL_PROVIDERS.WHATSAPP
@@ -63,7 +64,11 @@ const stackedCardState = call =>
 
 const toggleMute = () => {
   isMuted.value = !isMuted.value;
-  setWhatsappCallMuted(isMuted.value);
+  if (isWhatsappActive.value) {
+    setWhatsappCallMuted(isMuted.value);
+  } else {
+    TwilioVoiceClient.setMuted(isMuted.value);
+  }
 };
 
 watch(hasActiveCall, active => {
@@ -256,7 +261,7 @@ onBeforeUnmount(stopRingtone);
       :call-info="getCallInfo(activeCall || primaryIncomingCall)"
       :duration="hasActiveCall ? formattedCallDuration : ''"
       :is-muted="isMuted"
-      :show-mute="hasActiveCall && isWhatsappActive"
+      :show-mute="hasActiveCall"
       @accept="handleJoinCall(primaryIncomingCall)"
       @reject="rejectIncomingCall(primaryIncomingCall?.callSid)"
       @dismiss="dismissCall(primaryIncomingCall?.callSid)"
diff --git a/app/javascript/dashboard/components/widgets/WootWriter/Editor.vue b/app/javascript/dashboard/components/widgets/WootWriter/Editor.vue
index 3da526fc0..09dc23819 100644
--- a/app/javascript/dashboard/components/widgets/WootWriter/Editor.vue
+++ b/app/javascript/dashboard/components/widgets/WootWriter/Editor.vue
@@ -32,7 +32,6 @@ import {
   CONVERSATION_EVENTS,
   CAPTAIN_EVENTS,
 } from 'dashboard/helper/AnalyticsHelper/events';
-import { MESSAGE_EDITOR_IMAGE_RESIZES } from 'dashboard/constants/editor';
 
 import {
   messageSchema,
@@ -43,6 +42,7 @@ import {
   MessageMarkdownSerializer,
   EditorState,
   Selection,
+  imageResizeView,
 } from '@chatwoot/prosemirror-schema';
 import {
   suggestionsPlugin,
@@ -57,7 +57,6 @@ import {
   insertAtCursor,
   removeSignature as removeSignatureHelper,
   scrollCursorIntoView,
-  setURLWithQueryAndSize,
   getFormattingForEditor,
   getSelectionCoords,
   calculateMenuPosition,
@@ -72,6 +71,7 @@ import {
 import { createTypingIndicator } from '@chatwoot/utils';
 import { checkFileSizeLimit } from 'shared/helpers/FileHelper';
 import { uploadFile } from 'dashboard/helper/uploadHelper';
+import { INBOX_TYPES } from 'dashboard/helper/inbox';
 
 const props = defineProps({
   modelValue: { type: String, default: '' },
@@ -93,7 +93,6 @@ const props = defineProps({
   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 },
 });
 
@@ -119,6 +118,14 @@ const TYPING_INDICATOR_IDLE_TIME = 4000;
 const MAXIMUM_FILE_UPLOAD_SIZE = 4; // in MB
 const DEFAULT_FORMATTING = 'Context::Default';
 const PRIVATE_NOTE_FORMATTING = 'Context::PrivateNote';
+const MESSAGE_SIGNATURE_FORMATTING = 'Context::MessageSignature';
+const INLINE_IMAGE_PASTE_TYPES = [
+  'image/png',
+  'image/jpeg',
+  'image/jpg',
+  'image/gif',
+  'image/webp',
+];
 
 const effectiveChannelType = computed(() =>
   getEffectiveChannelType(props.channelType, props.medium)
@@ -192,12 +199,8 @@ const cannedSearchTerm = ref('');
 const variableSearchTerm = ref('');
 const emojiSearchTerm = ref('');
 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
 const editorRoot = useTemplateRef('editorRoot');
@@ -475,16 +478,6 @@ function removeSignature() {
   reloadState(content);
 }
 
-function setToolbarPosition() {
-  const editorRect = editorRoot.value.getBoundingClientRect();
-  const rect = selectedImageNode.value.getBoundingClientRect();
-
-  toolbarPosition.value = {
-    top: `${rect.top - editorRect.top - 30}px`,
-    left: `${rect.left - editorRect.left - 4}px`,
-  };
-}
-
 function setMenubarPosition({ selection } = {}) {
   const wrapper = editorRoot.value;
   if (!selection || !wrapper) return;
@@ -520,30 +513,6 @@ function checkSelection(editorState) {
   if (hasSelection) setMenubarPosition(editorState);
 }
 
-function setURLWithQueryAndImageSize(size) {
-  if (!props.showImageResizeToolbar) {
-    return;
-  }
-  setURLWithQueryAndSize(selectedImageNode.value, size, editorView);
-  isImageNodeSelected.value = false;
-}
-
-function isEditorMouseFocusedOnAnImage() {
-  if (!props.showImageResizeToolbar) {
-    return;
-  }
-  selectedImageNode.value = document.querySelector(
-    'img.ProseMirror-selectednode'
-  );
-  if (selectedImageNode.value) {
-    isImageNodeSelected.value = !!selectedImageNode.value;
-    // Get the position of the selected node
-    setToolbarPosition();
-  } else {
-    isImageNodeSelected.value = false;
-  }
-}
-
 function emitOnChange() {
   emit('input', contentFromEditor());
   emit('update:modelValue', contentFromEditor());
@@ -563,21 +532,6 @@ function toggleSignatureInEditor(signatureEnabled) {
   emitOnChange();
 }
 
-function updateImgToolbarOnDelete() {
-  // check if the selected node is present or not on keyup
-  // this is needed because the user can select an image and then delete it
-  // in that case, the selected node will be null and we need to hide the toolbar
-  // otherwise, the toolbar will be visible even when the image is deleted and cause some errors
-  if (selectedImageNode.value) {
-    const hasImgSelectedNode = document.querySelector(
-      'img.ProseMirror-selectednode'
-    );
-    if (!hasImgSelectedNode) {
-      isImageNodeSelected.value = false;
-    }
-  }
-}
-
 function isEnterToSendEnabled() {
   return isEditorHotKeyEnabled('enter');
 }
@@ -586,17 +540,6 @@ function isCmdPlusEnterToSendEnabled() {
   return isEditorHotKeyEnabled('cmd_enter');
 }
 
-useKeyboardEvents({
-  'Alt+KeyP': {
-    action: focusEditorInputField,
-    allowOnFocusedInput: false,
-  },
-  'Alt+KeyL': {
-    action: focusEditorInputField,
-    allowOnFocusedInput: false,
-  },
-});
-
 function onImageInsertInEditor(fileUrl) {
   const { tr } = editorView.state;
 
@@ -617,7 +560,11 @@ async function uploadImageToStorage(file) {
       onImageInsertInEditor(fileUrl);
     }
     useAlert(
-      t('PROFILE_SETTINGS.FORM.MESSAGE_SIGNATURE_SECTION.IMAGE_UPLOAD_SUCCESS')
+      props.channelType === MESSAGE_SIGNATURE_FORMATTING
+        ? t(
+            'PROFILE_SETTINGS.FORM.MESSAGE_SIGNATURE_SECTION.IMAGE_UPLOAD_SUCCESS'
+          )
+        : t('CONVERSATION.REPLYBOX.IMAGE_UPLOAD_SUCCESS')
     );
   } catch (error) {
     useAlert(
@@ -626,8 +573,8 @@ async function uploadImageToStorage(file) {
   }
 }
 
-function onFileChange() {
-  const file = imageUpload.value.files[0];
+function uploadImageIfWithinSizeLimit(file) {
+  if (!file) return;
   if (checkFileSizeLimit(file, MAXIMUM_FILE_UPLOAD_SIZE)) {
     uploadImageToStorage(file);
   } else {
@@ -640,10 +587,61 @@ function onFileChange() {
       )
     );
   }
-
-  imageUpload.value = '';
 }
 
+function onFileChange() {
+  const input = imageUpload.value;
+  uploadImageIfWithinSizeLimit(input.files[0]);
+  input.value = '';
+}
+
+const allowsInlineImagePaste = computed(
+  () =>
+    !props.isPrivate &&
+    (props.channelType === INBOX_TYPES.EMAIL ||
+      props.channelType === INBOX_TYPES.WEB)
+);
+
+// Shift+Cmd/Ctrl+V on email/website: upload a clipboard image inline. This
+// gesture's native paste event carries no image, so clipboard.read() is the
+// only way to get the bytes. No preventDefault: text still pastes natively.
+async function pasteInlineImageFromClipboard() {
+  if (!editorView?.hasFocus()) return;
+  if (!allowsInlineImagePaste.value || !navigator.clipboard?.read) return;
+  try {
+    const items = await navigator.clipboard.read();
+    const imageItem = items.find(item =>
+      item.types.some(type => INLINE_IMAGE_PASTE_TYPES.includes(type))
+    );
+    if (!imageItem) return;
+    const imageType = imageItem.types.find(type =>
+      INLINE_IMAGE_PASTE_TYPES.includes(type)
+    );
+    const blob = await imageItem.getType(imageType);
+    uploadImageIfWithinSizeLimit(
+      new File([blob], 'pasted-image', { type: imageType })
+    );
+  } catch (error) {
+    // clipboard-read denied/unfocused (NotAllowedError): image can't be read.
+    // Text paste is unaffected — ProseMirror handles it from the native event.
+  }
+}
+
+useKeyboardEvents({
+  'Alt+KeyP': {
+    action: focusEditorInputField,
+    allowOnFocusedInput: false,
+  },
+  'Alt+KeyL': {
+    action: focusEditorInputField,
+    allowOnFocusedInput: false,
+  },
+  '$mod+Shift+KeyV': {
+    action: pasteInlineImageFromClipboard,
+    allowOnFocusedInput: true,
+  },
+});
+
 function handleLineBreakWhenEnterToSendEnabled(event) {
   if (
     hasPressedEnterAndNotCmdOrShift(event) &&
@@ -736,6 +734,9 @@ function createEditorView() {
   editorView = new EditorView(editor.value, {
     state: state,
     editable: () => !props.disabled,
+    nodeViews: {
+      image: imageResizeView,
+    },
     dispatchTransaction: tx => {
       state = state.apply(tx);
       editorView.updateState(state);
@@ -748,12 +749,10 @@ function createEditorView() {
       keyup: () => {
         if (!props.disabled) {
           typingIndicator.start();
-          updateImgToolbarOnDelete();
         }
       },
       keydown: (view, event) => !props.disabled && onKeydown(event),
       focus: () => !props.disabled && emit('focus'),
-      click: () => !props.disabled && isEditorMouseFocusedOnAnImage(),
       blur: () => {
         if (props.disabled) return;
         typingIndicator.stop();
@@ -918,23 +917,6 @@ useEmitter(BUS_EVENTS.INSERT_INTO_RICH_EDITOR, insertContentIntoEditor);
       @change="onFileChange"
     />
     <div ref="editor" />
-    <div
-      v-show="isImageNodeSelected && showImageResizeToolbar"
-      class="absolute shadow-md rounded-[6px] flex gap-1 py-1 px-1 bg-n-solid-3 outline outline-1 outline-n-weak text-n-slate-12"
-      :style="{
-        top: toolbarPosition.top,
-        left: toolbarPosition.left,
-      }"
-    >
-      <button
-        v-for="size in sizes"
-        :key="size.name"
-        class="text-xs font-medium rounded-[4px] outline outline-1 outline-n-strong px-1.5 py-0.5 hover:bg-n-slate-5"
-        @click="setURLWithQueryAndImageSize(size)"
-      >
-        {{ size.name }}
-      </button>
-    </div>
     <slot name="footer" />
   </div>
 </template>
@@ -997,10 +979,6 @@ useEmitter(BUS_EVENTS.INSERT_INTO_RICH_EDITOR, insertContentIntoEditor);
         @apply text-n-slate-11;
       }
     }
-
-    ol li {
-      @apply list-item list-decimal;
-    }
   }
 }
 
diff --git a/app/javascript/dashboard/constants/editor.js b/app/javascript/dashboard/constants/editor.js
index 5528a9b43..95f63f206 100644
--- a/app/javascript/dashboard/constants/editor.js
+++ b/app/javascript/dashboard/constants/editor.js
@@ -14,6 +14,7 @@ export const FORMATTING = {
       'link',
       'bulletList',
       'orderedList',
+      'imageUpload',
       'undo',
       'redo',
     ],
@@ -30,6 +31,7 @@ export const FORMATTING = {
       'strike',
       'bulletList',
       'orderedList',
+      'imageUpload',
       'undo',
       'redo',
     ],
@@ -269,23 +271,3 @@ export const MARKDOWN_PATTERNS = [
     ],
   },
 ];
-
-// Editor image resize options for Message Editor
-export const MESSAGE_EDITOR_IMAGE_RESIZES = [
-  {
-    name: 'Small',
-    height: '24px',
-  },
-  {
-    name: 'Medium',
-    height: '48px',
-  },
-  {
-    name: 'Large',
-    height: '72px',
-  },
-  {
-    name: 'Original Size',
-    height: 'auto',
-  },
-];
diff --git a/app/javascript/dashboard/helper/editorHelper.js b/app/javascript/dashboard/helper/editorHelper.js
index e4330b332..32f56172a 100644
--- a/app/javascript/dashboard/helper/editorHelper.js
+++ b/app/javascript/dashboard/helper/editorHelper.js
@@ -379,31 +379,6 @@ export const findNodeToInsertImage = (editorState, fileUrl) => {
   };
 };
 
-/**
- * Set URL with query and size.
- *
- * @param {Object} selectedImageNode - The current selected node.
- * @param {Object} size - The size to set.
- * @param {Object} editorView - The editor view.
- */
-export function setURLWithQueryAndSize(selectedImageNode, size, editorView) {
-  if (selectedImageNode) {
-    // Create and apply the transaction
-    const tr = editorView.state.tr.setNodeMarkup(
-      editorView.state.selection.from,
-      null,
-      {
-        src: selectedImageNode.src,
-        height: size.height,
-      }
-    );
-
-    if (tr.docChanged) {
-      editorView.dispatch(tr);
-    }
-  }
-}
-
 /**
  * Strips unsupported markdown formatting from content based on the editor schema.
  * This ensures canned responses with rich formatting can be inserted into channels
diff --git a/app/javascript/dashboard/helper/specs/editorHelper.spec.js b/app/javascript/dashboard/helper/specs/editorHelper.spec.js
index 00d1e83d4..7d32f63e0 100644
--- a/app/javascript/dashboard/helper/specs/editorHelper.spec.js
+++ b/app/javascript/dashboard/helper/specs/editorHelper.spec.js
@@ -16,7 +16,6 @@ import {
   insertAtCursor,
   removeSignature,
   replaceSignature,
-  setURLWithQueryAndSize,
   stripInlineBase64Images,
   stripUnsupportedFormatting,
   stripUnsupportedMarkdown,
@@ -653,71 +652,6 @@ describe('findNodeToInsertImage', () => {
   });
 });
 
-describe('setURLWithQueryAndSize', () => {
-  let selectedNode;
-  let editorView;
-
-  beforeEach(() => {
-    selectedNode = {
-      setAttribute: vi.fn(),
-    };
-
-    const tr = {
-      setNodeMarkup: vi.fn().mockReturnValue({
-        docChanged: true,
-      }),
-    };
-
-    const state = {
-      selection: { from: 0 },
-      tr,
-    };
-
-    editorView = {
-      state,
-      dispatch: vi.fn(),
-    };
-  });
-
-  it('updates the URL with the given size and updates the editor view', () => {
-    const size = { height: '20px' };
-
-    setURLWithQueryAndSize(selectedNode, size, editorView);
-
-    // Check if the editor view is updated
-    expect(editorView.dispatch).toHaveBeenCalledTimes(1);
-  });
-
-  it('updates the URL with the given size and updates the editor view with original size', () => {
-    const size = { height: 'auto' };
-
-    setURLWithQueryAndSize(selectedNode, size, editorView);
-
-    // Check if the editor view is updated
-    expect(editorView.dispatch).toHaveBeenCalledTimes(1);
-  });
-
-  it('does not update the editor view if the document has not changed', () => {
-    editorView.state.tr.setNodeMarkup = vi.fn().mockReturnValue({
-      docChanged: false,
-    });
-
-    const size = { height: '20px' };
-
-    setURLWithQueryAndSize(selectedNode, size, editorView);
-
-    // Check if the editor view dispatch was not called
-    expect(editorView.dispatch).not.toHaveBeenCalled();
-  });
-
-  it('does not perform any operations if selectedNode is not provided', () => {
-    setURLWithQueryAndSize(null, { height: '20px' }, editorView);
-
-    // Ensure the dispatch method wasn't called
-    expect(editorView.dispatch).not.toHaveBeenCalled();
-  });
-});
-
 describe('getContentNode', () => {
   let mockEditorView;
 
diff --git a/app/javascript/dashboard/i18n/locale/en/conversation.json b/app/javascript/dashboard/i18n/locale/en/conversation.json
index 7b1b49493..3eb83fd31 100644
--- a/app/javascript/dashboard/i18n/locale/en/conversation.json
+++ b/app/javascript/dashboard/i18n/locale/en/conversation.json
@@ -233,6 +233,7 @@
       "TIP_AUDIORECORDER_ERROR": "Could not open the audio",
       "AUDIO_CONVERSION_FAILED": "Audio conversion failed. Please try again.",
       "DRAG_DROP": "Drag and drop here to attach",
+      "IMAGE_UPLOAD_SUCCESS": "Image uploaded successfully",
       "START_AUDIO_RECORDING": "Start audio recording",
       "STOP_AUDIO_RECORDING": "Stop audio recording",
       "COPILOT_THINKING": "Copilot is thinking",
diff --git a/app/javascript/dashboard/routes/dashboard/settings/profile/MessageSignature.vue b/app/javascript/dashboard/routes/dashboard/settings/profile/MessageSignature.vue
index b0dab9774..bf6f01f82 100644
--- a/app/javascript/dashboard/routes/dashboard/settings/profile/MessageSignature.vue
+++ b/app/javascript/dashboard/routes/dashboard/settings/profile/MessageSignature.vue
@@ -48,7 +48,6 @@ const updateSignature = () => {
       :placeholder="$t('PROFILE_SETTINGS.FORM.MESSAGE_SIGNATURE.PLACEHOLDER')"
       channel-type="Context::MessageSignature"
       :enable-suggestions="false"
-      show-image-resize-toolbar
     />
     <div>
       <NextButton
diff --git a/app/javascript/shared/helpers/MessageFormatter.js b/app/javascript/shared/helpers/MessageFormatter.js
index 825132e13..eb8fecf01 100644
--- a/app/javascript/shared/helpers/MessageFormatter.js
+++ b/app/javascript/shared/helpers/MessageFormatter.js
@@ -1,28 +1,37 @@
+import MarkdownIt from 'markdown-it';
 import mila from 'markdown-it-link-attributes';
 import mentionPlugin from './markdownIt/link';
-import MarkdownIt from 'markdown-it';
 
-const setImageHeight = inlineToken => {
+const setImageSizing = inlineToken => {
   const imgSrc = inlineToken.attrGet('src');
   if (!imgSrc) return;
   const url = new URL(imgSrc);
+  const width = url.searchParams.get('cw_image_width');
+  if (width) {
+    inlineToken.attrSet(
+      'style',
+      `width: ${width}; max-width: 100%; height: auto;`
+    );
+    return;
+  }
   const height = url.searchParams.get('cw_image_height');
-  if (!height) return;
-  inlineToken.attrSet('style', `height: ${height};`);
+  if (height) inlineToken.attrSet('style', `height: ${height};`);
 };
 
 const processInlineToken = blockToken => {
   blockToken.children.forEach(inlineToken => {
     if (inlineToken.type === 'image') {
-      setImageHeight(inlineToken);
+      setImageSizing(inlineToken);
     }
   });
 };
 
 const imgResizeManager = md => {
-  // Custom rule for image resize in markdown
-  // If the image url has a query param cw_image_height, then add a style attribute to the image
-  md.core.ruler.after('inline', 'add-image-height', state => {
+  // If the image URL carries a cw_image_width or cw_image_height query param,
+  // add an inline style attribute so the rendered <img> respects the agent's
+  // resize choice. Width takes precedence (HC drag-resize); height is kept for
+  // legacy messages and the message-signature use case.
+  md.core.ruler.after('inline', 'add-image-sizing', state => {
     state.tokens.forEach(blockToken => {
       if (blockToken.type === 'inline') {
         processInlineToken(blockToken);
diff --git a/app/javascript/widget/assets/scss/woot.scss b/app/javascript/widget/assets/scss/woot.scss
index b47179d29..c42273215 100755
--- a/app/javascript/widget/assets/scss/woot.scss
+++ b/app/javascript/widget/assets/scss/woot.scss
@@ -34,13 +34,24 @@ body {
 
 .message-content {
   ul {
-    list-style: disc;
-    @apply ltr:pl-3 rtl:pr-3;
+    @apply list-disc list-inside;
   }
 
   ol {
-    list-style: decimal;
-    @apply ltr:pl-4 rtl:pr-4;
+    @apply list-decimal list-inside;
+  }
+
+  li {
+    padding-inline-start: 1.5em;
+    text-indent: -1.5em;
+
+    > p:first-child {
+      @apply inline;
+    }
+
+    > * {
+      text-indent: 0;
+    }
   }
 }
 
diff --git a/app/mailers/conversation_reply_mailer_helper.rb b/app/mailers/conversation_reply_mailer_helper.rb
index dc3e0c3fd..88266c14d 100644
--- a/app/mailers/conversation_reply_mailer_helper.rb
+++ b/app/mailers/conversation_reply_mailer_helper.rb
@@ -54,8 +54,7 @@ module ConversationReplyMailerHelper
       tls: false,
       enable_starttls_auto: true,
       openssl_verify_mode: 'none',
-      open_timeout: 15,
-      read_timeout: 15,
+      **smtp_timeout_settings,
       authentication: 'xoauth2'
     }
   end
@@ -72,6 +71,7 @@ module ConversationReplyMailerHelper
       tls: @channel.smtp_enable_ssl_tls,
       enable_starttls_auto: @channel.smtp_enable_starttls_auto,
       openssl_verify_mode: @channel.smtp_openssl_verify_mode,
+      **smtp_timeout_settings,
       authentication: @channel.smtp_authentication
     }
 
@@ -79,6 +79,13 @@ module ConversationReplyMailerHelper
     @options[:delivery_method_options] = smtp_settings
   end
 
+  def smtp_timeout_settings
+    {
+      open_timeout: ENV['SMTP_OPEN_TIMEOUT'].presence || 15,
+      read_timeout: ENV['SMTP_READ_TIMEOUT'].presence || 30
+    }.transform_values(&:to_i)
+  end
+
   def email_smtp_enabled?
     @inbox.inbox_type == 'Email' && @channel.smtp_enabled
   end
diff --git a/app/models/portal.rb b/app/models/portal.rb
index 41c4d3edd..37665a15c 100644
--- a/app/models/portal.rb
+++ b/app/models/portal.rb
@@ -42,6 +42,7 @@ class Portal < ApplicationRecord
   validates :name, presence: true
   validates :slug, presence: true, uniqueness: true
   validates :custom_domain, uniqueness: true, allow_nil: true
+  validates :color, format: { with: /\A#(?:\h{3}|\h{6})\z/ }, allow_blank: true
   validate :config_json_format
 
   scope :active, -> { where(archived: false) }
diff --git a/app/services/imap/base_fetch_email_service.rb b/app/services/imap/base_fetch_email_service.rb
index 5a6d3537c..24dd22589 100644
--- a/app/services/imap/base_fetch_email_service.rb
+++ b/app/services/imap/base_fetch_email_service.rb
@@ -58,8 +58,9 @@ class Imap::BaseFetchEmailService
 
     return if email_already_present?(channel, message_id)
 
-    # Fetch the original mail content using the sequence no
-    mail_str = imap_client.fetch(seq_no, 'RFC822')[0].attr['RFC822']
+    # Fetch the original mail content using the sequence no.
+    # BODY.PEEK[] avoids RFC822 parser failures seen with some IMAP servers.
+    mail_str = imap_client.fetch(seq_no, 'BODY.PEEK[]')[0].attr['BODY[]']
 
     if mail_str.blank?
       Rails.logger.info "[IMAP::FETCH_EMAIL_SERVICE] Fetch failed for #{channel.email} with message-id <#{message_id}>."
diff --git a/app/services/messages/webhook_content_normalizer.rb b/app/services/messages/webhook_content_normalizer.rb
index b45f83ad0..5fa66fe9c 100644
--- a/app/services/messages/webhook_content_normalizer.rb
+++ b/app/services/messages/webhook_content_normalizer.rb
@@ -1,10 +1,11 @@
 # Strips CommonMark hard line breaks from stored markdown source (backslash before newline).
 # ProseMirror / the dashboard editor emits this form so soft breaks survive as markdown;
 # webhook consumers expect plain newlines without a visible backslash (e.g. WhatsApp gateways).
+# Also strips trailing newlines introduced by TipTap/ProseMirror trailing paragraph nodes.
 class Messages::WebhookContentNormalizer
   def self.normalize(text)
     return text if text.blank?
 
-    text.gsub(/\\\r?\n/, "\n")
+    text.gsub(/\\\r?\n/, "\n").sub(/(\r?\n)+\z/, '')
   end
 end
diff --git a/app/services/whatsapp/incoming_message_base_service.rb b/app/services/whatsapp/incoming_message_base_service.rb
index 722ac3e4d..9e0720f74 100644
--- a/app/services/whatsapp/incoming_message_base_service.rb
+++ b/app/services/whatsapp/incoming_message_base_service.rb
@@ -147,7 +147,7 @@ class Whatsapp::IncomingMessageBaseService
 
   def attach_location
     location = messages_data.first['location']
-    location_name = location['name'] ? "#{location['name']}, #{location['address']}" : ''
+    location_name = (location['name'] ? "#{location['name']}, #{location['address']}" : '').first(255)
     @message.attachments.new(
       account_id: @message.account_id,
       file_type: file_content_type(message_type),
diff --git a/app/views/super_admin/application/_icons.html.erb b/app/views/super_admin/application/_icons.html.erb
index e80d1e164..39253c969 100644
--- a/app/views/super_admin/application/_icons.html.erb
+++ b/app/views/super_admin/application/_icons.html.erb
@@ -128,6 +128,10 @@
     <path d="M18.3 10.2H19.2C19.4387 10.2 19.6676 10.2948 19.8364 10.4636C20.0052 10.6324 20.1 10.8613 20.1 11.1V20.1C20.1 20.3387 20.0052 20.5676 19.8364 20.7364C19.6676 20.9052 19.4387 21 19.2 21H4.80002C4.56133 21 4.33241 20.9052 4.16363 20.7364C3.99485 20.5676 3.90002 20.3387 3.90002 20.1V11.1C3.90002 10.8613 3.99485 10.6324 4.16363 10.4636C4.33241 10.2948 4.56133 10.2 4.80002 10.2H5.70002V9.3C5.70002 8.47267 5.86298 7.65345 6.17958 6.88909C6.49619 6.12474 6.96024 5.43024 7.54525 4.84523C8.13026 4.26022 8.82477 3.79616 9.58912 3.47956C10.3535 3.16295 11.1727 3 12 3C12.8274 3 13.6466 3.16295 14.4109 3.47956C15.1753 3.79616 15.8698 4.26022 16.4548 4.84523C17.0398 5.43024 17.5039 6.12474 17.8205 6.88909C18.1371 7.65345 18.3 8.47267 18.3 9.3V10.2ZM5.70002 12V19.2H18.3V12H5.70002ZM11.1 13.8H12.9V17.4H11.1V13.8ZM16.5 10.2V9.3C16.5 8.10653 16.0259 6.96193 15.182 6.11802C14.3381 5.27411 13.1935 4.8 12 4.8C10.8066 4.8 9.66196 5.27411 8.81804 6.11802C7.97413 6.96193 7.50002 8.10653 7.50002 9.3V10.2H16.5Z" fill="currentColor"/>
   </symbol>
 
+  <symbol id="icon-voice-line" viewBox="0 0 24 24">
+    <g fill="none" stroke="currentColor"><path d="M12.75 4.50031C14.5402 4.50031 16.2571 5.21146 17.523 6.47733C18.7888 7.7432 19.5 9.46009 19.5 11.2503" stroke-width="1.5" stroke-linecap="round" stroke-linejoin="round"/><path d="M12.75 7.5C13.7446 7.5 14.6984 7.89509 15.4017 8.59835C16.1049 9.30161 16.5 10.2554 16.5 11.25" stroke-width="1.5" stroke-linecap="round" stroke-linejoin="round"/><path d="M13.374 15.4263C13.5289 15.4974 13.7034 15.5137 13.8688 15.4724C14.0341 15.4311 14.1805 15.3347 14.2837 15.1991L14.55 14.8503C14.6897 14.664 14.8709 14.5128 15.0792 14.4087C15.2875 14.3045 15.5171 14.2503 15.75 14.2503H18C18.3978 14.2503 18.7794 14.4083 19.0607 14.6896C19.342 14.9709 19.5 15.3525 19.5 15.7503V18.0003C19.5 18.3981 19.342 18.7797 19.0607 19.061C18.7794 19.3423 18.3978 19.5003 18 19.5003C14.4196 19.5003 10.9858 18.078 8.45406 15.5462C5.92232 13.0145 4.5 9.58073 4.5 6.00031C4.5 5.60248 4.65804 5.22095 4.93934 4.93964C5.22064 4.65834 5.60218 4.50031 6 4.50031H8.25C8.64782 4.50031 9.02935 4.65834 9.31066 4.93964C9.59196 5.22095 9.75 5.60248 9.75 6.00031V8.2503C9.75 8.48317 9.69578 8.71284 9.59164 8.92113C9.4875 9.12941 9.33629 9.31058 9.15 9.45031L8.799 9.71355C8.66131 9.81869 8.56426 9.96824 8.52434 10.1368C8.48442 10.3054 8.50409 10.4826 8.58 10.6383C9.60501 12.7202 11.2908 14.4039 13.374 15.4263Z" stroke-width="1.5" stroke-linecap="round" stroke-linejoin="round"/></g>
+  </symbol>
+
   <symbol id="icon-captain" viewBox="0 0 24 24">
     <path d="M7.02051 9.50216C7.02051 9.01881 7.41237 8.62695 7.89571 8.62695C8.37909 8.62695 8.77091 9.01881 8.77091 9.50216V11.5248C8.77091 12.0082 8.37909 12.4 7.89571 12.4C7.41237 12.4 7.02051 12.0082 7.02051 11.5248V9.50216Z" fill="currentColor"/>
     <path d="M9.82117 9.50216C9.82117 9.01881 10.213 8.62695 10.6964 8.62695C11.1798 8.62695 11.5716 9.01881 11.5716 9.50216V11.5248C11.5716 12.0082 11.1798 12.4 10.6964 12.4C10.213 12.4 9.82117 12.0082 9.82117 11.5248V9.50216Z" fill="currentColor"/>
diff --git a/enterprise/app/helpers/captain/chat_generation_recorder.rb b/enterprise/app/helpers/captain/chat_generation_recorder.rb
index cd631fb16..63bcdc276 100644
--- a/enterprise/app/helpers/captain/chat_generation_recorder.rb
+++ b/enterprise/app/helpers/captain/chat_generation_recorder.rb
@@ -10,6 +10,7 @@ module Captain::ChatGenerationRecorder
     # Create a generation span with model and token info for Langfuse cost calculation.
     # Note: span duration will be near-zero since we create and end it immediately, but token counts are what Langfuse uses for cost calculation.
     tracer.in_span("llm.captain.#{feature_name}.generation") do |span|
+      apply_current_langfuse_attributes(span)
       set_generation_span_attributes(span, chat, message)
     end
   rescue StandardError => e
@@ -37,11 +38,23 @@ module Captain::ChatGenerationRecorder
       ATTR_GEN_AI_USAGE_INPUT_TOKENS => message.input_tokens,
       ATTR_GEN_AI_USAGE_OUTPUT_TOKENS => message.respond_to?(:output_tokens) ? message.output_tokens : nil,
       ATTR_LANGFUSE_OBSERVATION_INPUT => format_input_messages(chat),
-      ATTR_LANGFUSE_OBSERVATION_OUTPUT => message.respond_to?(:content) ? message.content.to_s : nil
+      ATTR_LANGFUSE_OBSERVATION_OUTPUT => message.respond_to?(:content) ? message.content.to_s : nil,
+      format(ATTR_LANGFUSE_OBSERVATION_METADATA, 'generation_stage') => generation_stage(message)
     }
   end
 
   def format_input_messages(chat)
     chat.messages[0...-1].map { |m| { role: m.role.to_s, content: m.content.to_s } }.to_json
   end
+
+  def generation_stage(message)
+    message_has_tool_calls?(message) ? 'tool_call' : 'final_response'
+  end
+
+  def message_has_tool_calls?(message)
+    return false unless message.respond_to?(:tool_calls)
+
+    tool_calls = message.tool_calls
+    tool_calls.respond_to?(:any?) && tool_calls.any?
+  end
 end
diff --git a/enterprise/app/services/captain/tools/firecrawl_service.rb b/enterprise/app/services/captain/tools/firecrawl_service.rb
index bee7219e8..6797634a2 100644
--- a/enterprise/app/services/captain/tools/firecrawl_service.rb
+++ b/enterprise/app/services/captain/tools/firecrawl_service.rb
@@ -1,5 +1,5 @@
 class Captain::Tools::FirecrawlService
-  BASE_URL = 'https://api.firecrawl.dev/v1'.freeze
+  BASE_URL = 'https://api.firecrawl.dev/v2'.freeze
   FIRECRAWL_EXCLUDE_TAGS = %w[iframe .sidebar .cookie-banner [role=navigation] [role=banner] [role=contentinfo]].freeze
 
   def self.configured?
@@ -35,10 +35,10 @@ class Captain::Tools::FirecrawlService
   def crawl_payload(url, webhook_url, crawl_limit)
     {
       url: url,
-      maxDepth: 50,
-      ignoreSitemap: false,
+      maxDiscoveryDepth: 50,
+      sitemap: 'include',
       limit: crawl_limit,
-      webhook: webhook_url,
+      webhook: { url: webhook_url },
       scrapeOptions: scrape_options
     }.to_json
   end
@@ -51,7 +51,8 @@ class Captain::Tools::FirecrawlService
     {
       onlyMainContent: true,
       formats: ['markdown'],
-      excludeTags: FIRECRAWL_EXCLUDE_TAGS
+      excludeTags: FIRECRAWL_EXCLUDE_TAGS,
+      maxAge: 0
     }
   end
 
diff --git a/lib/base_markdown_renderer.rb b/lib/base_markdown_renderer.rb
index f530e71ee..2329dea6d 100644
--- a/lib/base_markdown_renderer.rb
+++ b/lib/base_markdown_renderer.rb
@@ -1,9 +1,9 @@
 class BaseMarkdownRenderer < CommonMarker::HtmlRenderer
   def image(node)
     src, title = extract_img_attributes(node)
-    height = extract_image_height(src)
+    sizing_style = extract_image_sizing_style(src)
 
-    render_img_tag(src, title, height)
+    render_img_tag(src, title, sizing_style)
   end
 
   private
@@ -15,9 +15,25 @@ class BaseMarkdownRenderer < CommonMarker::HtmlRenderer
     ]
   end
 
-  def extract_image_height(src)
+  # Drag-resize from the reply editor encodes the chosen width as cw_image_width
+  # on the URL; the older message-signature picker uses cw_image_height. Width
+  # wins when both are set so the agent's most recent intent is honored.
+  def extract_image_sizing_style(src)
     query_params = parse_query_params(src)
-    query_params['cw_image_height']&.first
+    width = sanitize_pixel_value(query_params['cw_image_width']&.first)
+    return "width: #{width}; max-width: 100%; height: auto;" if width
+
+    height = sanitize_pixel_value(query_params['cw_image_height']&.first)
+    height ? "height: #{height};" : nil
+  end
+
+  # Only allow a bounded `<digits>px` value so the decoded query param can't
+  # break out of the inline style attribute (HTML attribute injection).
+  def sanitize_pixel_value(raw)
+    return unless raw =~ /\A(\d+)px\z/
+
+    px = Regexp.last_match(1).to_i
+    "#{px}px" if px.between?(1, 2000)
   end
 
   def parse_query_params(url)
@@ -27,13 +43,13 @@ class BaseMarkdownRenderer < CommonMarker::HtmlRenderer
     {}
   end
 
-  def render_img_tag(src, title, height = nil)
+  def render_img_tag(src, title, sizing_style = nil)
     title_attribute = title.present? ? " title=\"#{title}\"" : ''
-    # Use inline style instead of the HTML height attribute: email clients and
-    # the in-app Letter view both run images through CSS (e.g. prose /
+    # Use inline style instead of HTML width/height attributes: email clients
+    # and the in-app Letter view both run images through CSS (e.g. prose /
     # lettersanitizer's `img { height: auto }`) which overrides presentational
     # attributes. Inline style has higher specificity and survives.
-    style_attribute = height ? " style=\"height: #{height};\"" : ''
+    style_attribute = sizing_style ? " style=\"#{sizing_style}\"" : ''
 
     plain do
       # plain ensures that the content is not wrapped in a paragraph tag
diff --git a/lib/captain/tool_instrumentation.rb b/lib/captain/tool_instrumentation.rb
index 157aab829..3c4a1c76e 100644
--- a/lib/captain/tool_instrumentation.rb
+++ b/lib/captain/tool_instrumentation.rb
@@ -10,12 +10,14 @@ module Captain::ToolInstrumentation
 
     response = nil
     executed = false
-    tracer.in_span(params[:span_name]) do |span|
-      set_tool_session_attributes(span, params)
-      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)
+    with_propagated_langfuse_attributes(params) do
+      tracer.in_span(params[:span_name]) do |span|
+        set_tool_session_attributes(span, params)
+        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
     end
     response
   rescue StandardError => e
@@ -24,9 +26,7 @@ module Captain::ToolInstrumentation
   end
 
   def set_tool_session_attributes(span, params)
-    span.set_attribute(ATTR_LANGFUSE_USER_ID, params[:account_id].to_s) if params[:account_id]
-    span.set_attribute(ATTR_LANGFUSE_SESSION_ID, "#{params[:account_id]}_#{params[:conversation_id]}") if params[:conversation_id].present?
-    span.set_attribute(ATTR_LANGFUSE_TAGS, [params[:feature_name]].to_json)
+    set_metadata_attributes(span, params)
     span.set_attribute(ATTR_LANGFUSE_OBSERVATION_INPUT, params[:messages].to_json)
   end
 
@@ -43,6 +43,7 @@ module Captain::ToolInstrumentation
     return unless message.respond_to?(:role) && message.role.to_s == 'assistant'
 
     tracer.in_span("llm.#{event_name}.generation") do |span|
+      apply_current_langfuse_attributes(span)
       span.set_attribute(ATTR_GEN_AI_PROVIDER, 'openai')
       span.set_attribute(ATTR_GEN_AI_REQUEST_MODEL, model)
       span.set_attribute(ATTR_GEN_AI_USAGE_INPUT_TOKENS, message.input_tokens)
diff --git a/lib/integrations/llm_instrumentation.rb b/lib/integrations/llm_instrumentation.rb
index 326bb901e..0257f5c3a 100644
--- a/lib/integrations/llm_instrumentation.rb
+++ b/lib/integrations/llm_instrumentation.rb
@@ -29,16 +29,18 @@ module Integrations::LlmInstrumentation
 
     result = nil
     executed = false
-    tracer.in_span(params[:span_name]) do |span|
-      set_metadata_attributes(span, params)
+    with_propagated_langfuse_attributes(params) do
+      tracer.in_span(params[:span_name]) do |span|
+        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)
-      set_error_attributes(span, result) if result.is_a?(Hash)
-      result
+        # 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)
+        set_error_attributes(span, result) if result.is_a?(Hash)
+        result
+      end
     end
   rescue StandardError => e
     ChatwootExceptionTracker.new(e, account: resolve_account(params)).capture_exception
@@ -51,6 +53,7 @@ module Integrations::LlmInstrumentation
     return yield unless ChatwootApp.otel_enabled?
 
     tracer.in_span(format(TOOL_SPAN_NAME, tool_name)) do |span|
+      apply_current_langfuse_attributes(span)
       span.set_attribute(ATTR_LANGFUSE_OBSERVATION_TYPE, 'tool')
       span.set_attribute(ATTR_LANGFUSE_OBSERVATION_INPUT, arguments.to_json)
       result = yield
@@ -96,23 +99,6 @@ module Integrations::LlmInstrumentation
     end
   end
 
-  def instrument_with_span(span_name, params, &)
-    result = nil
-    executed = false
-    tracer.in_span(span_name) do |span|
-      track_result = lambda do |r|
-        executed = true
-        result = r
-      end
-      yield(span, track_result)
-    end
-  rescue StandardError => e
-    ChatwootExceptionTracker.new(e, account: resolve_account(params)).capture_exception
-    raise unless executed
-
-    result
-  end
-
   private
 
   def resolve_account(params)
diff --git a/lib/integrations/llm_instrumentation_completion_helpers.rb b/lib/integrations/llm_instrumentation_completion_helpers.rb
index 551d0780f..26af2aae1 100644
--- a/lib/integrations/llm_instrumentation_completion_helpers.rb
+++ b/lib/integrations/llm_instrumentation_completion_helpers.rb
@@ -10,7 +10,6 @@ module Integrations::LlmInstrumentationCompletionHelpers
     span.set_attribute(ATTR_GEN_AI_REQUEST_MODEL, params[:model])
     span.set_attribute('embedding.input_length', params[:input]&.length || 0)
     span.set_attribute(ATTR_LANGFUSE_OBSERVATION_INPUT, params[:input].to_s)
-    set_common_span_metadata(span, params)
   end
 
   def set_audio_transcription_span_attributes(span, params)
@@ -18,7 +17,6 @@ module Integrations::LlmInstrumentationCompletionHelpers
     span.set_attribute(ATTR_GEN_AI_REQUEST_MODEL, params[:model] || 'whisper-1')
     span.set_attribute('audio.duration_seconds', params[:duration]) if params[:duration]
     span.set_attribute(ATTR_LANGFUSE_OBSERVATION_INPUT, params[:file_path].to_s) if params[:file_path]
-    set_common_span_metadata(span, params)
   end
 
   def set_moderation_span_attributes(span, params)
@@ -26,12 +24,6 @@ module Integrations::LlmInstrumentationCompletionHelpers
     span.set_attribute(ATTR_GEN_AI_REQUEST_MODEL, params[:model] || 'text-moderation-latest')
     span.set_attribute('moderation.input_length', params[:input]&.length || 0)
     span.set_attribute(ATTR_LANGFUSE_OBSERVATION_INPUT, params[:input].to_s)
-    set_common_span_metadata(span, params)
-  end
-
-  def set_common_span_metadata(span, params)
-    span.set_attribute(ATTR_LANGFUSE_USER_ID, params[:account_id].to_s) if params[:account_id]
-    span.set_attribute(ATTR_LANGFUSE_TAGS, [params[:feature_name]].to_json) if params[:feature_name]
   end
 
   def set_embedding_result_attributes(span, result)
diff --git a/lib/integrations/llm_instrumentation_constants.rb b/lib/integrations/llm_instrumentation_constants.rb
index dfe1e7704..f274d1145 100644
--- a/lib/integrations/llm_instrumentation_constants.rb
+++ b/lib/integrations/llm_instrumentation_constants.rb
@@ -29,4 +29,5 @@ module Integrations::LlmInstrumentationConstants
   ATTR_LANGFUSE_OBSERVATION_TYPE = 'langfuse.observation.type'
   ATTR_LANGFUSE_OBSERVATION_INPUT = 'langfuse.observation.input'
   ATTR_LANGFUSE_OBSERVATION_OUTPUT = 'langfuse.observation.output'
+  ATTR_LANGFUSE_OBSERVATION_METADATA = 'langfuse.observation.metadata.%s'
 end
diff --git a/lib/integrations/llm_instrumentation_context.rb b/lib/integrations/llm_instrumentation_context.rb
new file mode 100644
index 000000000..27b1eb2b2
--- /dev/null
+++ b/lib/integrations/llm_instrumentation_context.rb
@@ -0,0 +1,41 @@
+# frozen_string_literal: true
+
+module Integrations::LlmInstrumentationContext
+  LANGFUSE_ATTRIBUTES_KEY = :llm_instrumentation_langfuse_attributes
+  LANGFUSE_OBSERVATION_METADATA_KEY = :llm_instrumentation_langfuse_observation_metadata_attributes
+
+  private
+
+  def with_propagated_langfuse_attributes(params)
+    previous_attributes = current_langfuse_attributes
+    previous_observation_metadata_attributes = current_observation_metadata_attributes
+    self.current_langfuse_attributes = previous_attributes.merge(propagated_langfuse_attributes(params))
+    self.current_observation_metadata_attributes = previous_observation_metadata_attributes.merge(propagated_observation_metadata_attributes(params))
+
+    yield
+  ensure
+    self.current_langfuse_attributes = previous_attributes
+    self.current_observation_metadata_attributes = previous_observation_metadata_attributes
+  end
+
+  def apply_current_langfuse_attributes(span)
+    set_langfuse_attributes(span, current_langfuse_attributes)
+    set_langfuse_attributes(span, current_observation_metadata_attributes)
+  end
+
+  def current_langfuse_attributes
+    ActiveSupport::IsolatedExecutionState[LANGFUSE_ATTRIBUTES_KEY] || {}
+  end
+
+  def current_langfuse_attributes=(attrs)
+    ActiveSupport::IsolatedExecutionState[LANGFUSE_ATTRIBUTES_KEY] = attrs
+  end
+
+  def current_observation_metadata_attributes
+    ActiveSupport::IsolatedExecutionState[LANGFUSE_OBSERVATION_METADATA_KEY] || {}
+  end
+
+  def current_observation_metadata_attributes=(attrs)
+    ActiveSupport::IsolatedExecutionState[LANGFUSE_OBSERVATION_METADATA_KEY] = attrs
+  end
+end
diff --git a/lib/integrations/llm_instrumentation_helpers.rb b/lib/integrations/llm_instrumentation_helpers.rb
index 129092ed4..debbfaeda 100644
--- a/lib/integrations/llm_instrumentation_helpers.rb
+++ b/lib/integrations/llm_instrumentation_helpers.rb
@@ -2,6 +2,7 @@
 
 module Integrations::LlmInstrumentationHelpers
   include Integrations::LlmInstrumentationConstants
+  include Integrations::LlmInstrumentationContext
   include Integrations::LlmInstrumentationCompletionHelpers
 
   def determine_provider(model_name)
@@ -51,15 +52,55 @@ module Integrations::LlmInstrumentationHelpers
   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)
+    set_langfuse_attributes(span, current_langfuse_attributes.merge(propagated_langfuse_attributes(params)))
+    set_langfuse_attributes(span, current_observation_metadata_attributes.merge(propagated_observation_metadata_attributes(params)))
+  end
 
-    return unless params[:metadata].is_a?(Hash)
+  def propagated_langfuse_attributes(params)
+    attrs = {}
+    session_id = params[:conversation_id].present? ? "#{params[:account_id]}_#{params[:conversation_id]}" : nil
+
+    attrs[ATTR_LANGFUSE_USER_ID] = params[:account_id].to_s if params[:account_id]
+    attrs[ATTR_LANGFUSE_SESSION_ID] = session_id if session_id.present?
+    attrs[ATTR_LANGFUSE_TAGS] = [params[:feature_name].to_s] if params[:feature_name].present?
+
+    return attrs unless params[:metadata].is_a?(Hash)
 
     params[:metadata].each do |key, value|
-      span.set_attribute(format(ATTR_LANGFUSE_METADATA, key), value.to_s)
+      attrs[format(ATTR_LANGFUSE_METADATA, key)] = value.to_s
+    end
+
+    attrs
+  end
+
+  def propagated_observation_metadata_attributes(params)
+    attrs = {}
+    session_id = params[:conversation_id].present? ? "#{params[:account_id]}_#{params[:conversation_id]}" : nil
+
+    add_observation_metadata(attrs, 'user_id', params[:account_id])
+    add_observation_metadata(attrs, 'account_id', params[:account_id])
+    add_observation_metadata(attrs, 'session_id', session_id)
+    add_observation_metadata(attrs, 'trace_tags', [params[:feature_name]].to_json)
+    add_observation_metadata(attrs, 'feature_name', params[:feature_name])
+
+    return attrs unless params[:metadata].is_a?(Hash)
+
+    params[:metadata].each do |key, value|
+      add_observation_metadata(attrs, key, value)
+    end
+
+    attrs
+  end
+
+  def add_observation_metadata(attrs, key, value)
+    return if value.blank?
+
+    attrs[format(ATTR_LANGFUSE_OBSERVATION_METADATA, key)] = value.to_s
+  end
+
+  def set_langfuse_attributes(span, attrs)
+    attrs.each do |key, value|
+      span.set_attribute(key, value)
     end
   end
 end
diff --git a/lib/integrations/llm_instrumentation_spans.rb b/lib/integrations/llm_instrumentation_spans.rb
index 85ea599f8..2def9749d 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))
+    apply_current_langfuse_attributes(span)
     span.set_attribute(ATTR_LANGFUSE_OBSERVATION_TYPE, 'tool')
     span.set_attribute(ATTR_LANGFUSE_OBSERVATION_INPUT, tool_call.arguments.to_json)
 
@@ -61,6 +62,24 @@ module Integrations::LlmInstrumentationSpans
     Rails.logger.warn "Failed to end tool span: #{e.message}"
   end
 
+  def instrument_with_span(span_name, params, &)
+    result = nil
+    executed = false
+    tracer.in_span(span_name) do |span|
+      set_metadata_attributes(span, params)
+      track_result = lambda do |r|
+        executed = true
+        result = r
+      end
+      yield(span, track_result)
+    end
+  rescue StandardError => e
+    ChatwootExceptionTracker.new(e, account: resolve_account(params)).capture_exception
+    raise unless executed
+
+    result
+  end
+
   private
 
   def set_llm_turn_request_attributes(span, params)
diff --git a/lib/opentelemetry_config.rb b/lib/opentelemetry_config.rb
index 5ed17e098..32be413d0 100644
--- a/lib/opentelemetry_config.rb
+++ b/lib/opentelemetry_config.rb
@@ -72,7 +72,10 @@ module OpentelemetryConfig
 
       config = {
         endpoint: traces_endpoint,
-        headers: { 'Authorization' => "Basic #{auth_header}" }
+        headers: {
+          'Authorization' => "Basic #{auth_header}",
+          'x-langfuse-ingestion-version' => '4'
+        }
       }
 
       config[:ssl_verify_mode] = OpenSSL::SSL::VERIFY_NONE if Rails.env.development?
diff --git a/package.json b/package.json
index 081c706c6..d8527051d 100644
--- a/package.json
+++ b/package.json
@@ -34,7 +34,7 @@
     "@amplitude/analytics-browser": "^2.11.10",
     "@breezystack/lamejs": "^1.2.7",
     "@chatwoot/ninja-keys": "1.2.3",
-    "@chatwoot/prosemirror-schema": "1.3.13",
+    "@chatwoot/prosemirror-schema": "1.3.17",
     "@chatwoot/utils": "^0.0.55",
     "@formkit/core": "^1.7.2",
     "@formkit/vue": "^1.7.2",
diff --git a/pnpm-lock.yaml b/pnpm-lock.yaml
index afcf5b60f..a4b61061c 100644
--- a/pnpm-lock.yaml
+++ b/pnpm-lock.yaml
@@ -25,8 +25,8 @@ importers:
         specifier: 1.2.3
         version: 1.2.3
       '@chatwoot/prosemirror-schema':
-        specifier: 1.3.13
-        version: 1.3.13
+        specifier: 1.3.17
+        version: 1.3.17
       '@chatwoot/utils':
         specifier: ^0.0.55
         version: 0.0.55
@@ -458,8 +458,8 @@ packages:
   '@chatwoot/ninja-keys@1.2.3':
     resolution: {integrity: sha512-xM8d9P5ikDMZm2WbaCTk/TW5HFauylrU3cJ75fq5je6ixKwyhl/0kZbVN/vbbZN4+AUX/OaSIn6IJbtCgIF67g==}
 
-  '@chatwoot/prosemirror-schema@1.3.13':
-    resolution: {integrity: sha512-T6FBUinMJbwDCD7975g8M/Tsn2+G3O2pTGIXdcLkMRpbAAC6mVdl4ZcZektlt5y/PVmPVqNHPsfee1XB/C3vAw==}
+  '@chatwoot/prosemirror-schema@1.3.17':
+    resolution: {integrity: sha512-n78ZfMIzSrylImIN5cjCeEdTJ8ub0JtCybwUlqFyOyLy3ZzAZpOHvCSo+w/KmV4dCgOH2mBmYlxBQ9Rww+e0Rw==}
 
   '@chatwoot/utils@0.0.55':
     resolution: {integrity: sha512-8G6HYQe1ZEYfJEsSYfDVvE+uhf98JDRjtGlpB+bzMko+yltbrk4yACSo/ImC3jSaJ6K8yPTSjJToSRmsQbL2iQ==}
@@ -5128,7 +5128,7 @@ snapshots:
       hotkeys-js: 3.8.7
       lit: 2.2.6
 
-  '@chatwoot/prosemirror-schema@1.3.13':
+  '@chatwoot/prosemirror-schema@1.3.17':
     dependencies:
       markdown-it-sup: 2.0.0
       prosemirror-commands: 1.7.1
diff --git a/public/audio/dashboard/ringtone.mp3 b/public/audio/dashboard/ringtone.mp3
new file mode 100644
index 000000000..c2af2b6d1
Binary files /dev/null and b/public/audio/dashboard/ringtone.mp3 differ
diff --git a/spec/controllers/api/v1/accounts/microsoft/authorization_controller_spec.rb b/spec/controllers/api/v1/accounts/microsoft/authorization_controller_spec.rb
index 60b05b36c..18a26a393 100644
--- a/spec/controllers/api/v1/accounts/microsoft/authorization_controller_spec.rb
+++ b/spec/controllers/api/v1/accounts/microsoft/authorization_controller_spec.rb
@@ -43,6 +43,7 @@ RSpec.describe 'Microsoft Authorization API', type: :request do
         ]
         expect(params['scope']).to eq(expected_scope)
         expect(params['redirect_uri']).to eq(["#{ENV.fetch('FRONTEND_URL', 'http://localhost:3000')}/microsoft/callback"])
+        expect(url).not_to match(/(?:\?|&)prompt=/)
 
         # Validate state parameter exists and can be decoded back to the account
         expect(params['state']).to be_present
diff --git a/spec/enterprise/services/captain/llm/assistant_chat_service_spec.rb b/spec/enterprise/services/captain/llm/assistant_chat_service_spec.rb
index 9d233943e..6b2cc55c8 100644
--- a/spec/enterprise/services/captain/llm/assistant_chat_service_spec.rb
+++ b/spec/enterprise/services/captain/llm/assistant_chat_service_spec.rb
@@ -39,6 +39,30 @@ RSpec.describe Captain::Llm::AssistantChatService do
       allow(mock_chat).to receive(:ask).and_return(mock_response)
       service.generate_response(message_history: [{ role: 'user', content: 'Hello' }])
     end
+
+    it 'marks final response generations for observation-level evaluators' do
+      service = described_class.new(assistant: assistant, conversation: conversation)
+      message = instance_double(RubyLLM::Message, content: 'Final answer', input_tokens: 10, output_tokens: 20, tool_calls: {})
+
+      attributes = service.send(:generation_attributes, mock_chat, message)
+
+      expect(attributes['langfuse.observation.metadata.generation_stage']).to eq('final_response')
+    end
+
+    it 'marks tool call generations separately from final responses' do
+      service = described_class.new(assistant: assistant, conversation: conversation)
+      message = instance_double(
+        RubyLLM::Message,
+        content: '',
+        input_tokens: 10,
+        output_tokens: 20,
+        tool_calls: { 'call_1' => instance_double(RubyLLM::ToolCall) }
+      )
+
+      attributes = service.send(:generation_attributes, mock_chat, message)
+
+      expect(attributes['langfuse.observation.metadata.generation_stage']).to eq('tool_call')
+    end
   end
 
   describe 'image analysis' do
diff --git a/spec/enterprise/services/captain/tools/firecrawl_service_spec.rb b/spec/enterprise/services/captain/tools/firecrawl_service_spec.rb
index 4d4bc7aaf..9a099fc67 100644
--- a/spec/enterprise/services/captain/tools/firecrawl_service_spec.rb
+++ b/spec/enterprise/services/captain/tools/firecrawl_service_spec.rb
@@ -53,14 +53,15 @@ RSpec.describe Captain::Tools::FirecrawlService do
     let(:expected_payload) do
       {
         url: url,
-        maxDepth: 50,
-        ignoreSitemap: false,
+        maxDiscoveryDepth: 50,
+        sitemap: 'include',
         limit: crawl_limit,
-        webhook: webhook_url,
+        webhook: { url: webhook_url },
         scrapeOptions: {
           onlyMainContent: true,
           formats: ['markdown'],
-          excludeTags: Captain::Tools::FirecrawlService::FIRECRAWL_EXCLUDE_TAGS
+          excludeTags: Captain::Tools::FirecrawlService::FIRECRAWL_EXCLUDE_TAGS,
+          maxAge: 0
         }
       }.to_json
     end
@@ -74,7 +75,7 @@ RSpec.describe Captain::Tools::FirecrawlService do
 
     context 'when the API call is successful' do
       before do
-        stub_request(:post, 'https://api.firecrawl.dev/v1/crawl')
+        stub_request(:post, 'https://api.firecrawl.dev/v2/crawl')
           .with(
             body: expected_payload,
             headers: expected_headers
@@ -85,7 +86,7 @@ RSpec.describe Captain::Tools::FirecrawlService do
       it 'makes a POST request with correct parameters' do
         service.perform(url, webhook_url, crawl_limit)
 
-        expect(WebMock).to have_requested(:post, 'https://api.firecrawl.dev/v1/crawl')
+        expect(WebMock).to have_requested(:post, 'https://api.firecrawl.dev/v2/crawl')
           .with(
             body: expected_payload,
             headers: expected_headers
@@ -95,7 +96,7 @@ RSpec.describe Captain::Tools::FirecrawlService do
       it 'uses default crawl limit when not specified' do
         default_payload = expected_payload.gsub(crawl_limit.to_s, '10')
 
-        stub_request(:post, 'https://api.firecrawl.dev/v1/crawl')
+        stub_request(:post, 'https://api.firecrawl.dev/v2/crawl')
           .with(
             body: default_payload,
             headers: expected_headers
@@ -104,7 +105,7 @@ RSpec.describe Captain::Tools::FirecrawlService do
 
         service.perform(url, webhook_url)
 
-        expect(WebMock).to have_requested(:post, 'https://api.firecrawl.dev/v1/crawl')
+        expect(WebMock).to have_requested(:post, 'https://api.firecrawl.dev/v2/crawl')
           .with(
             body: default_payload,
             headers: expected_headers
@@ -114,7 +115,7 @@ RSpec.describe Captain::Tools::FirecrawlService do
 
     context 'when the API call fails' do
       before do
-        stub_request(:post, 'https://api.firecrawl.dev/v1/crawl')
+        stub_request(:post, 'https://api.firecrawl.dev/v2/crawl')
           .to_raise(StandardError.new('Connection failed'))
       end
 
@@ -126,14 +127,14 @@ RSpec.describe Captain::Tools::FirecrawlService do
 
     context 'when the API returns an error response' do
       before do
-        stub_request(:post, 'https://api.firecrawl.dev/v1/crawl')
+        stub_request(:post, 'https://api.firecrawl.dev/v2/crawl')
           .to_return(status: 422, body: '{"error": "Invalid URL"}')
       end
 
       it 'makes the request but does not raise an error' do
         expect { service.perform(url, webhook_url, crawl_limit) }.not_to raise_error
 
-        expect(WebMock).to have_requested(:post, 'https://api.firecrawl.dev/v1/crawl')
+        expect(WebMock).to have_requested(:post, 'https://api.firecrawl.dev/v2/crawl')
           .with(
             body: expected_payload,
             headers: expected_headers
diff --git a/spec/lib/base_markdown_renderer_spec.rb b/spec/lib/base_markdown_renderer_spec.rb
index f8bdae4be..082f9fff6 100644
--- a/spec/lib/base_markdown_renderer_spec.rb
+++ b/spec/lib/base_markdown_renderer_spec.rb
@@ -11,8 +11,33 @@ describe BaseMarkdownRenderer do
   describe '#image' do
     context 'when image has a height' do
       it 'renders the img tag with the correct attributes' do
-        markdown = '![Sample Title](https://example.com/image.jpg?cw_image_height=100)'
-        expect(render_markdown(markdown)).to include('<img src="https://example.com/image.jpg?cw_image_height=100" style="height: 100;" />')
+        markdown = '![Sample Title](https://example.com/image.jpg?cw_image_height=100px)'
+        expect(render_markdown(markdown)).to include('<img src="https://example.com/image.jpg?cw_image_height=100px" style="height: 100px;" />')
+      end
+    end
+
+    context 'when image has a width' do
+      it 'renders the img tag with the correct attributes' do
+        markdown = '![Sample Title](https://example.com/image.jpg?cw_image_width=200px)'
+        expect(render_markdown(markdown)).to include(
+          '<img src="https://example.com/image.jpg?cw_image_width=200px" style="width: 200px; max-width: 100%; height: auto;" />'
+        )
+      end
+    end
+
+    context 'when the sizing param contains an attribute-injection payload' do
+      it 'drops the malicious height value' do
+        markdown = '![x](https://example.com/image.jpg?cw_image_height=1px%22%20onmouseover%3D%22alert(1))'
+        rendered = render_markdown(markdown)
+        expect(rendered).not_to include('style=')
+        expect(rendered).not_to include('onmouseover="')
+      end
+
+      it 'drops the malicious width value' do
+        markdown = '![x](https://example.com/image.jpg?cw_image_width=1px%22%20onmouseover%3D%22alert(1))'
+        rendered = render_markdown(markdown)
+        expect(rendered).not_to include('style=')
+        expect(rendered).not_to include('onmouseover="')
       end
     end
 
diff --git a/spec/lib/integrations/llm_instrumentation_spec.rb b/spec/lib/integrations/llm_instrumentation_spec.rb
index 0be62f437..f291cd7b2 100644
--- a/spec/lib/integrations/llm_instrumentation_spec.rb
+++ b/spec/lib/integrations/llm_instrumentation_spec.rb
@@ -144,7 +144,10 @@ RSpec.describe Integrations::LlmInstrumentation do
 
         expect(mock_span).to have_received(:set_attribute).with('langfuse.user.id', '123')
         expect(mock_span).to have_received(:set_attribute).with('langfuse.session.id', '123_456')
-        expect(mock_span).to have_received(:set_attribute).with('langfuse.trace.tags', '["reply_suggestion"]')
+        expect(mock_span).to have_received(:set_attribute).with('langfuse.trace.tags', ['reply_suggestion'])
+        expect(mock_span).to have_received(:set_attribute).with('langfuse.observation.metadata.user_id', '123')
+        expect(mock_span).to have_received(:set_attribute).with('langfuse.observation.metadata.session_id', '123_456')
+        expect(mock_span).to have_received(:set_attribute).with('langfuse.observation.metadata.feature_name', 'reply_suggestion')
       end
 
       it 'sets completion message attributes when result contains message' do
@@ -253,6 +256,76 @@ RSpec.describe Integrations::LlmInstrumentation do
           expect(mock_span).to have_received(:set_attribute).with('langfuse.observation.output', result_data.to_json)
         end
 
+        it 'propagates trace attributes as observation metadata to child tool spans' do
+          root_span = instance_double(OpenTelemetry::Trace::Span)
+          tool_span = instance_double(OpenTelemetry::Trace::Span)
+          tool_instance = test_class.new
+          allow(root_span).to receive(:set_attribute)
+          allow(tool_span).to receive(:set_attribute)
+          allow(instance).to receive(:tracer).and_return(mock_tracer)
+          allow(tool_instance).to receive(:tracer).and_return(mock_tracer)
+          allow(mock_tracer).to receive(:in_span).with('llm.test').and_yield(root_span)
+          allow(mock_tracer).to receive(:in_span).with('tool.search').and_yield(tool_span)
+
+          instance.instrument_agent_session(params) do
+            tool_instance.instrument_tool_call('search', { query: 'test' }) { 'tool result' }
+          end
+
+          expect(tool_span).to have_received(:set_attribute).with('langfuse.observation.metadata.user_id', '123')
+          expect(tool_span).to have_received(:set_attribute).with('langfuse.observation.metadata.session_id', '123_456')
+          expect(tool_span).to have_received(:set_attribute).with('langfuse.observation.metadata.feature_name', 'reply_suggestion')
+        end
+
+        it 'keeps inherited session metadata for nested service spans with their own feature tag' do
+          root_span = instance_double(OpenTelemetry::Trace::Span)
+          nested_span = instance_double(OpenTelemetry::Trace::Span)
+          nested_instance = test_class.new
+          nested_params = params.merge(span_name: 'llm.translate_query', conversation_id: nil, feature_name: 'translate_query')
+          allow(root_span).to receive(:set_attribute)
+          allow(nested_span).to receive(:set_attribute)
+          allow(instance).to receive(:tracer).and_return(mock_tracer)
+          allow(nested_instance).to receive(:tracer).and_return(mock_tracer)
+          allow(mock_tracer).to receive(:in_span).with('llm.test').and_yield(root_span)
+          allow(mock_tracer).to receive(:in_span).with('llm.translate_query').and_yield(nested_span)
+
+          instance.instrument_agent_session(params) do
+            nested_instance.instrument_llm_call(nested_params) { 'translated query' }
+          end
+
+          expect(nested_span).to have_received(:set_attribute).with('langfuse.session.id', '123_456')
+          expect(nested_span).to have_received(:set_attribute).with('langfuse.trace.tags', ['translate_query'])
+          expect(nested_span).to have_received(:set_attribute).with('langfuse.observation.metadata.session_id', '123_456')
+          expect(nested_span).to have_received(:set_attribute).with('langfuse.observation.metadata.feature_name', 'translate_query')
+        end
+
+        it 'propagates session metadata to nested embedding spans' do
+          root_span = instance_double(OpenTelemetry::Trace::Span)
+          embedding_span = instance_double(OpenTelemetry::Trace::Span)
+          embedding_instance = test_class.new
+          embedding_params = {
+            span_name: 'llm.captain.embedding',
+            account_id: 123,
+            feature_name: 'embedding',
+            model: 'text-embedding-3-small',
+            input: 'search result'
+          }
+          allow(root_span).to receive(:set_attribute)
+          allow(embedding_span).to receive(:set_attribute)
+          allow(instance).to receive(:tracer).and_return(mock_tracer)
+          allow(embedding_instance).to receive(:tracer).and_return(mock_tracer)
+          allow(mock_tracer).to receive(:in_span).with('llm.test').and_yield(root_span)
+          allow(mock_tracer).to receive(:in_span).with('llm.captain.embedding').and_yield(embedding_span)
+
+          instance.instrument_agent_session(params) do
+            embedding_instance.instrument_embedding_call(embedding_params) { [0.1, 0.2, 0.3] }
+          end
+
+          expect(embedding_span).to have_received(:set_attribute).with('langfuse.session.id', '123_456')
+          expect(embedding_span).to have_received(:set_attribute).with('langfuse.trace.tags', ['embedding'])
+          expect(embedding_span).to have_received(:set_attribute).with('langfuse.observation.metadata.session_id', '123_456')
+          expect(embedding_span).to have_received(:set_attribute).with('langfuse.observation.metadata.feature_name', 'embedding')
+        end
+
         # Regression test for Langfuse double-counting bug.
         # Setting gen_ai.request.model on parent spans causes Langfuse to classify them as
         # GENERATIONs instead of SPANs, resulting in cost being counted multiple times
diff --git a/spec/mailers/conversation_reply_mailer_spec.rb b/spec/mailers/conversation_reply_mailer_spec.rb
index 86a2363e9..df4c4f41f 100644
--- a/spec/mailers/conversation_reply_mailer_spec.rb
+++ b/spec/mailers/conversation_reply_mailer_spec.rb
@@ -462,6 +462,26 @@ RSpec.describe ConversationReplyMailer do
         expect(mail.delivery_method.settings.empty?).to be false
         expect(mail.delivery_method.settings[:address]).to eq 'smtp.gmail.com'
         expect(mail.delivery_method.settings[:port]).to eq 587
+        expect(mail.delivery_method.settings[:open_timeout]).to eq 15
+        expect(mail.delivery_method.settings[:read_timeout]).to eq 30
+      end
+
+      it 'uses configured smtp timeout values' do
+        with_modified_env SMTP_OPEN_TIMEOUT: '10', SMTP_READ_TIMEOUT: '30' do
+          mail = described_class.email_reply(message)
+
+          expect(mail.delivery_method.settings[:open_timeout]).to eq 10
+          expect(mail.delivery_method.settings[:read_timeout]).to eq 30
+        end
+      end
+
+      it 'uses default smtp timeout values when env values are blank' do
+        with_modified_env SMTP_OPEN_TIMEOUT: '', SMTP_READ_TIMEOUT: '' do
+          mail = described_class.email_reply(message)
+
+          expect(mail.delivery_method.settings[:open_timeout]).to eq 15
+          expect(mail.delivery_method.settings[:read_timeout]).to eq 30
+        end
       end
 
       it 'renders sender name in the from address' do
diff --git a/spec/services/imap/fetch_email_service_spec.rb b/spec/services/imap/fetch_email_service_spec.rb
index a40a46343..1f74cf0b7 100644
--- a/spec/services/imap/fetch_email_service_spec.rb
+++ b/spec/services/imap/fetch_email_service_spec.rb
@@ -80,11 +80,11 @@ RSpec.describe Imap::FetchEmailService do
         travel_to '26.10.2020 10:00'.to_datetime do
           email_object = create_inbound_email_from_fixture('only_text.eml')
           email_header = Net::IMAP::FetchData.new(1, 'BODY[HEADER]' => eml_content_with_message_id)
-          imap_fetch_mail = Net::IMAP::FetchData.new(1, 'RFC822' => eml_content_with_message_id)
+          imap_fetch_mail = Net::IMAP::FetchData.new(1, 'BODY[]' => eml_content_with_message_id)
 
           allow(imap).to receive(:search).with(%w[SINCE 25-Oct-2020]).and_return([1])
           allow(imap).to receive(:fetch).with([1], 'BODY.PEEK[HEADER]').and_return([email_header])
-          allow(imap).to receive(:fetch).with(1, 'RFC822').and_return([imap_fetch_mail])
+          allow(imap).to receive(:fetch).with(1, 'BODY.PEEK[]').and_return([imap_fetch_mail])
           allow(imap).to receive(:logout)
 
           result = described_class.new(channel: imap_email_channel).perform
@@ -93,7 +93,7 @@ RSpec.describe Imap::FetchEmailService do
           expect(result[0].message_id).to eq email_object.message_id
           expect(imap).to have_received(:search).with(%w[SINCE 25-Oct-2020])
           expect(imap).to have_received(:fetch).with([1], 'BODY.PEEK[HEADER]')
-          expect(imap).to have_received(:fetch).with(1, 'RFC822')
+          expect(imap).to have_received(:fetch).with(1, 'BODY.PEEK[]')
           expect(logger).to have_received(:info).with("[IMAP::FETCH_EMAIL_SERVICE] Fetching mails from #{imap_email_channel.email}, found 1.")
           expect(imap).to have_received(:logout)
         end
@@ -115,7 +115,7 @@ RSpec.describe Imap::FetchEmailService do
           expect(result.length).to eq 0
           expect(imap).to have_received(:search).with(%w[SINCE 25-Oct-2020])
           expect(imap).to have_received(:fetch).with([1], 'BODY.PEEK[HEADER]')
-          expect(imap).not_to have_received(:fetch).with(1, 'RFC822')
+          expect(imap).not_to have_received(:fetch).with(1, 'BODY.PEEK[]')
         end
       end
 
@@ -129,12 +129,12 @@ RSpec.describe Imap::FetchEmailService do
             Net::IMAP::FetchData.new(seq_num, 'BODY[HEADER]' => eml_content_without_message_id)
           end
           valid_email_header = Net::IMAP::FetchData.new(valid_message_seq_num, 'BODY[HEADER]' => eml_content_with_message_id)
-          imap_fetch_mail = Net::IMAP::FetchData.new(valid_message_seq_num, 'RFC822' => eml_content_with_message_id)
+          imap_fetch_mail = Net::IMAP::FetchData.new(valid_message_seq_num, 'BODY[]' => eml_content_with_message_id)
 
           allow(imap).to receive(:search).with(%w[SINCE 25-Oct-2020]).and_return(empty_message_id_seq_nums + [valid_message_seq_num])
           allow(imap).to receive(:fetch).with(empty_message_id_seq_nums, 'BODY.PEEK[HEADER]').and_return(empty_message_id_headers)
           allow(imap).to receive(:fetch).with([valid_message_seq_num], 'BODY.PEEK[HEADER]').and_return([valid_email_header])
-          allow(imap).to receive(:fetch).with(valid_message_seq_num, 'RFC822').and_return([imap_fetch_mail])
+          allow(imap).to receive(:fetch).with(valid_message_seq_num, 'BODY.PEEK[]').and_return([imap_fetch_mail])
           allow(imap).to receive(:logout)
 
           result = described_class.new(channel: imap_email_channel).perform
@@ -143,7 +143,7 @@ RSpec.describe Imap::FetchEmailService do
           expect(result[0].message_id).to eq email_object.message_id
           expect(imap).to have_received(:fetch).with(empty_message_id_seq_nums, 'BODY.PEEK[HEADER]')
           expect(imap).to have_received(:fetch).with([valid_message_seq_num], 'BODY.PEEK[HEADER]')
-          expect(imap).to have_received(:fetch).with(valid_message_seq_num, 'RFC822')
+          expect(imap).to have_received(:fetch).with(valid_message_seq_num, 'BODY.PEEK[]')
         end
       end
     end
diff --git a/spec/services/imap/microsoft_fetch_email_service_spec.rb b/spec/services/imap/microsoft_fetch_email_service_spec.rb
index a4a0a62d1..cc20d5b35 100644
--- a/spec/services/imap/microsoft_fetch_email_service_spec.rb
+++ b/spec/services/imap/microsoft_fetch_email_service_spec.rb
@@ -30,11 +30,11 @@ RSpec.describe Imap::MicrosoftFetchEmailService do
         travel_to '26.10.2020 10:00'.to_datetime do
           email_object = create_inbound_email_from_fixture('only_text.eml')
           email_header = Net::IMAP::FetchData.new(1, 'BODY[HEADER]' => eml_content_with_message_id)
-          imap_fetch_mail = Net::IMAP::FetchData.new(1, 'RFC822' => eml_content_with_message_id)
+          imap_fetch_mail = Net::IMAP::FetchData.new(1, 'BODY[]' => eml_content_with_message_id)
 
           allow(imap).to receive(:search).with(%w[SINCE 25-Oct-2020]).and_return([1])
           allow(imap).to receive(:fetch).with([1], 'BODY.PEEK[HEADER]').and_return([email_header])
-          allow(imap).to receive(:fetch).with(1, 'RFC822').and_return([imap_fetch_mail])
+          allow(imap).to receive(:fetch).with(1, 'BODY.PEEK[]').and_return([imap_fetch_mail])
           allow(imap).to receive(:logout)
 
           result = described_class.new(channel: microsoft_channel).perform
@@ -45,7 +45,7 @@ RSpec.describe Imap::MicrosoftFetchEmailService do
           expect(result[0].message_id).to eq email_object.message_id
           expect(imap).to have_received(:search).with(%w[SINCE 25-Oct-2020])
           expect(imap).to have_received(:fetch).with([1], 'BODY.PEEK[HEADER]')
-          expect(imap).to have_received(:fetch).with(1, 'RFC822')
+          expect(imap).to have_received(:fetch).with(1, 'BODY.PEEK[]')
           expect(logger).to have_received(:info).with("[IMAP::FETCH_EMAIL_SERVICE] Fetching mails from #{microsoft_channel.email}, found 1.")
         end
       end
@@ -56,11 +56,11 @@ RSpec.describe Imap::MicrosoftFetchEmailService do
         travel_to '26.10.2020 10:00'.to_datetime do
           email_object = create_inbound_email_from_fixture('only_text.eml')
           email_header = Net::IMAP::FetchData.new(1, 'BODY[HEADER]' => eml_content_with_message_id)
-          imap_fetch_mail = Net::IMAP::FetchData.new(1, 'RFC822' => eml_content_with_message_id)
+          imap_fetch_mail = Net::IMAP::FetchData.new(1, 'BODY[]' => eml_content_with_message_id)
 
           allow(imap).to receive(:search).with(%w[SINCE 18-Oct-2020]).and_return([1])
           allow(imap).to receive(:fetch).with([1], 'BODY.PEEK[HEADER]').and_return([email_header])
-          allow(imap).to receive(:fetch).with(1, 'RFC822').and_return([imap_fetch_mail])
+          allow(imap).to receive(:fetch).with(1, 'BODY.PEEK[]').and_return([imap_fetch_mail])
           allow(imap).to receive(:logout)
 
           result = described_class.new(channel: microsoft_channel, interval: 8).perform
@@ -71,7 +71,7 @@ RSpec.describe Imap::MicrosoftFetchEmailService do
           expect(result[0].message_id).to eq email_object.message_id
           expect(imap).to have_received(:search).with(%w[SINCE 18-Oct-2020])
           expect(imap).to have_received(:fetch).with([1], 'BODY.PEEK[HEADER]')
-          expect(imap).to have_received(:fetch).with(1, 'RFC822')
+          expect(imap).to have_received(:fetch).with(1, 'BODY.PEEK[]')
           expect(logger).to have_received(:info).with("[IMAP::FETCH_EMAIL_SERVICE] Fetching mails from #{microsoft_channel.email}, found 1.")
         end
       end
diff --git a/spec/services/messages/webhook_content_normalizer_spec.rb b/spec/services/messages/webhook_content_normalizer_spec.rb
new file mode 100644
index 000000000..ca5023b9d
--- /dev/null
+++ b/spec/services/messages/webhook_content_normalizer_spec.rb
@@ -0,0 +1,41 @@
+require 'rails_helper'
+
+RSpec.describe Messages::WebhookContentNormalizer do
+  describe '.normalize' do
+    it 'returns nil unchanged' do
+      expect(described_class.normalize(nil)).to be_nil
+    end
+
+    it 'returns blank string unchanged' do
+      expect(described_class.normalize('')).to eq('')
+    end
+
+    it 'strips trailing newlines added by TipTap/ProseMirror' do
+      expect(described_class.normalize("hello\n\n\n")).to eq('hello')
+    end
+
+    it 'preserves intentional trailing spaces' do
+      expect(described_class.normalize("hello   \n\n")).to eq('hello   ')
+    end
+
+    it 'replaces CommonMark hard line breaks (backslash-newline) with plain newlines' do
+      expect(described_class.normalize("hello\\\nworld")).to eq("hello\nworld")
+    end
+
+    it 'replaces CommonMark hard line breaks with CRLF with plain newlines' do
+      expect(described_class.normalize("hello\\\r\nworld")).to eq("hello\nworld")
+    end
+
+    it 'preserves intentional internal newlines' do
+      expect(described_class.normalize("line one\nline two")).to eq("line one\nline two")
+    end
+
+    it 'strips trailing CRLF newlines without leaving dangling carriage returns' do
+      expect(described_class.normalize("hello\r\n\r\n")).to eq('hello')
+    end
+
+    it 'handles both hard line breaks and trailing newlines together' do
+      expect(described_class.normalize("hello\\\nworld\n\n\n")).to eq("hello\nworld")
+    end
+  end
+end
diff --git a/spec/services/whatsapp/incoming_message_service_spec.rb b/spec/services/whatsapp/incoming_message_service_spec.rb
index fe6b179c1..430aa1561 100644
--- a/spec/services/whatsapp/incoming_message_service_spec.rb
+++ b/spec/services/whatsapp/incoming_message_service_spec.rb
@@ -381,6 +381,32 @@ describe Whatsapp::IncomingMessageService do
         expect(location_attachment.coordinates_long).to eq(-122.3895553)
         expect(location_attachment.external_url).to eq('http://location_url.test')
       end
+
+      it 'truncates long fallback titles to avoid dropping location messages' do
+        long_place_name = [
+          'Gremi de Fusters, 33, Edificio VIP Asima, Piso 2, Local 2, Norte',
+          '07009 Poligon industrial de Son Castello, Illes Balears, Espana'
+        ].join(', ')
+        source_id = 'wamid.long-location-fallback-title'
+        params = {
+          'contacts' => [{ 'profile' => { 'name' => 'Sojan Jose' }, 'wa_id' => '2423423243' }],
+          'messages' => [{ 'from' => '2423423243', 'id' => source_id,
+                           'location' => { 'id' => 'b1c68f38-8734-4ad3-b4a1-ef0c10d683',
+                                           :address => long_place_name,
+                                           :latitude => 37.7893768,
+                                           :longitude => -122.3895553,
+                                           :name => long_place_name,
+                                           :url => 'http://location_url.test' },
+                           'timestamp' => '1633034394', 'type' => 'location' }]
+        }.with_indifferent_access
+
+        expect { described_class.new(inbox: whatsapp_channel.inbox, params: params).perform }
+          .to change { Message.where(source_id: source_id).count }.from(0).to(1)
+
+        location_attachment = Message.find_by!(source_id: source_id).attachments.first
+        expect(location_attachment.fallback_title).to eq("#{long_place_name}, #{long_place_name}".first(255))
+        expect(location_attachment.fallback_title.length).to eq(255)
+      end
     end
 
     context 'when valid contact message params' do
diff --git a/tailwind.config.js b/tailwind.config.js
index b4c4b9078..cc2aebb63 100644
--- a/tailwind.config.js
+++ b/tailwind.config.js
@@ -106,24 +106,30 @@ const tailwindConfig = {
               textDecoration: 'underline',
             },
             ul: {
-              paddingInlineStart: '0.625em',
+              paddingInlineStart: '0',
+              listStylePosition: 'inside',
             },
             ol: {
-              paddingInlineStart: '0.625em',
+              paddingInlineStart: '0',
+              listStylePosition: 'inside',
             },
-            'ul li': {
-              margin: '0 0 0.5em 1em',
+            'ul > li': {
+              marginBlockEnd: '0.5em',
               listStyleType: 'disc',
-              '[dir="rtl"] &': {
-                margin: '0 1em 0.5em 0',
-              },
+              paddingInlineStart: '1.5em',
+              textIndent: '-1.5em',
             },
-            'ol li': {
-              margin: '0 0 0.5em 1em',
+            'ol > li': {
+              marginBlockEnd: '0.5em',
               listStyleType: 'decimal',
-              '[dir="rtl"] &': {
-                margin: '0 1em 0.5em 0',
-              },
+              paddingInlineStart: '1.5em',
+              textIndent: '-1.5em',
+            },
+            'li > p:first-child': {
+              display: 'inline',
+            },
+            'li > *': {
+              textIndent: '0',
             },
             blockquote: {
               color: 'rgb(var(--slate-11))',