diff --git a/app/javascript/dashboard/components-next/captain/assistant/DocumentCard.vue b/app/javascript/dashboard/components-next/captain/assistant/DocumentCard.vue
index 9d6d574ec..8ff38b2eb 100644
--- a/app/javascript/dashboard/components-next/captain/assistant/DocumentCard.vue
+++ b/app/javascript/dashboard/components-next/captain/assistant/DocumentCard.vue
@@ -66,6 +66,10 @@ const props = defineProps({
     type: Number,
     default: null,
   },
+  responsesCount: {
+    type: Number,
+    default: 0,
+  },
   isSelected: {
     type: Boolean,
     default: false,
@@ -112,10 +116,10 @@ const showSyncStatus = computed(() => !isPdf.value);
 const menuItems = computed(() => {
   const allOptions = [
     {
-      label: t('CAPTAIN.DOCUMENTS.OPTIONS.VIEW_RELATED_RESPONSES'),
-      value: 'viewRelatedQuestions',
-      action: 'viewRelatedQuestions',
-      icon: 'i-ph-tree-view-duotone',
+      label: t('CAPTAIN.DOCUMENTS.OPTIONS.VIEW_DETAILS'),
+      value: 'viewDetails',
+      action: 'viewDetails',
+      icon: 'i-lucide-eye',
     },
   ];
 
@@ -143,6 +147,9 @@ const menuItems = computed(() => {
 });
 
 const createdAtLabel = computed(() => dynamicTime(props.createdAt));
+const responsesCountLabel = computed(() =>
+  t('CAPTAIN.DOCUMENTS.FAQ_COUNT', { n: props.responsesCount })
+);
 
 const displayLink = computed(() =>
   isPdf.value
@@ -158,6 +165,10 @@ const handleAction = ({ action, value }) => {
   emit('action', { action, value, id: props.id });
 };
 
+const handleViewDetails = () => {
+  emit('action', { action: 'viewDetails', id: props.id });
+};
+
 const handleRetry = () => {
   emit('action', { action: 'sync', id: props.id });
 };
@@ -177,9 +188,13 @@ const handleRetry = () => {
       <Checkbox v-model="modelValue" />
     </div>
     <div class="flex gap-1 justify-between w-full">
-      <span class="text-base text-n-slate-12 line-clamp-1">
+      <button
+        type="button"
+        class="p-0 text-base text-left bg-transparent border-0 outline-transparent text-n-slate-12 line-clamp-1 underline-offset-2 hover:underline focus-visible:underline"
+        @click="handleViewDetails"
+      >
         {{ name }}
-      </span>
+      </button>
       <div v-if="showMenu" class="flex gap-2 items-center">
         <div
           v-on-clickaway="() => toggleDropdown(false)"
@@ -228,6 +243,9 @@ const handleRetry = () => {
         <Icon :icon="linkIcon" class="shrink-0" />
         <span class="truncate">{{ displayLink }}</span>
       </span>
+      <span class="text-sm shrink-0 text-n-slate-11">
+        {{ responsesCountLabel }}
+      </span>
       <DocumentSyncStatus
         v-if="showSyncStatus"
         :status="syncStatus"
diff --git a/app/javascript/dashboard/components-next/captain/pageComponents/document/DocumentDetails.spec.js b/app/javascript/dashboard/components-next/captain/pageComponents/document/DocumentDetails.spec.js
new file mode 100644
index 000000000..9fde9a57e
--- /dev/null
+++ b/app/javascript/dashboard/components-next/captain/pageComponents/document/DocumentDetails.spec.js
@@ -0,0 +1,86 @@
+import { flushPromises, shallowMount } from '@vue/test-utils';
+import DocumentDetails from './DocumentDetails.vue';
+
+const { dispatch, getterValues } = vi.hoisted(() => ({
+  dispatch: vi.fn(),
+  getterValues: {
+    'captainResponses/getUIFlags': { value: { fetchingList: false } },
+    'captainResponses/getRecords': { value: [] },
+    'captainResponses/getMeta': { value: { totalCount: 26, page: 1 } },
+  },
+}));
+
+vi.mock('dashboard/composables/store', () => ({
+  useStore: () => ({ dispatch }),
+  useMapGetter: key => getterValues[key],
+}));
+
+vi.mock('dashboard/composables', () => ({ useAlert: vi.fn() }));
+
+vi.mock('vue-i18n', () => ({
+  useI18n: () => ({ t: key => key }),
+}));
+
+const captainDocument = {
+  id: 42,
+  name: 'FAQ source',
+  external_link: 'https://example.com/docs',
+  assistant: { id: 7 },
+  content: 'Document content',
+  pdf_document: false,
+};
+
+const DialogStub = {
+  name: 'Dialog',
+  template: '<div><slot /></div>',
+};
+
+const TabBarStub = {
+  name: 'TabBar',
+  template:
+    '<button data-test="faq-tab" @click="$emit(\'tabChanged\', { key: \'faqs\' })" />',
+};
+
+const PaginationFooterStub = {
+  name: 'PaginationFooter',
+  template:
+    '<button data-test="next-page" @click="$emit(\'update:currentPage\', 2)" />',
+};
+
+describe('DocumentDetails', () => {
+  beforeEach(() => {
+    vi.clearAllMocks();
+    dispatch.mockResolvedValue([]);
+  });
+
+  it('requests another FAQ page when the document has more than 25 FAQs', async () => {
+    const wrapper = shallowMount(DocumentDetails, {
+      props: { captainDocument },
+      global: {
+        directives: { dompurifyHtml: {} },
+        stubs: {
+          Dialog: DialogStub,
+          TabBar: TabBarStub,
+          PaginationFooter: PaginationFooterStub,
+        },
+      },
+    });
+
+    await flushPromises();
+
+    expect(dispatch).toHaveBeenCalledWith('captainResponses/get', {
+      page: 1,
+      assistantId: 7,
+      documentId: 42,
+    });
+
+    await wrapper.get('[data-test="faq-tab"]').trigger('click');
+    await wrapper.get('[data-test="next-page"]').trigger('click');
+
+    expect(dispatch).toHaveBeenLastCalledWith('captainResponses/get', {
+      page: 2,
+      assistantId: 7,
+      documentId: 42,
+    });
+  });
+});
diff --git a/app/javascript/dashboard/components-next/captain/pageComponents/document/DocumentDetails.vue b/app/javascript/dashboard/components-next/captain/pageComponents/document/DocumentDetails.vue
new file mode 100644
index 000000000..eadb0b480
--- /dev/null
+++ b/app/javascript/dashboard/components-next/captain/pageComponents/document/DocumentDetails.vue
@@ -0,0 +1,374 @@
+<script setup>
+import { ref, computed, onMounted } from 'vue';
+import { useStore, useMapGetter } from 'dashboard/composables/store';
+import { useAlert } from 'dashboard/composables';
+import { useI18n } from 'vue-i18n';
+import { messageTimestamp } from 'shared/helpers/timeHelper';
+import { copyTextToClipboard } from 'shared/helpers/clipboard';
+import MessageFormatter from 'shared/helpers/MessageFormatter';
+import {
+  isSafeHttpLink,
+  formatDocumentLink,
+  getDocumentDisplayPath,
+} from 'shared/helpers/documentHelper';
+import Spinner from 'dashboard/components-next/spinner/Spinner.vue';
+import Dialog from 'dashboard/components-next/dialog/Dialog.vue';
+import Icon from 'dashboard/components-next/icon/Icon.vue';
+import Button from 'dashboard/components-next/button/Button.vue';
+import TabBar from 'dashboard/components-next/tabbar/TabBar.vue';
+import PaginationFooter from 'dashboard/components-next/pagination/PaginationFooter.vue';
+import ResponseCard from '../../assistant/ResponseCard.vue';
+
+const props = defineProps({
+  captainDocument: {
+    type: Object,
+    required: true,
+  },
+});
+const emit = defineEmits(['close']);
+const TAB_KEYS = {
+  CONTENT: 'content',
+  FAQS: 'faqs',
+};
+const RESPONSES_PER_PAGE = 25;
+const { t } = useI18n();
+const store = useStore();
+const dialogRef = ref(null);
+const documentDetails = computed(() => props.captainDocument);
+const showRawContent = ref(false);
+const activeTabIndex = ref(0);
+
+const uiFlags = useMapGetter('captainResponses/getUIFlags');
+const responses = useMapGetter('captainResponses/getRecords');
+const meta = useMapGetter('captainResponses/getMeta');
+const isFetching = computed(() => uiFlags.value.fetchingList);
+const totalCount = computed(() => meta.value.totalCount || 0);
+const currentPage = computed(() => meta.value.page || 1);
+const showPaginationFooter = computed(
+  () => totalCount.value > RESPONSES_PER_PAGE
+);
+const documentContent = computed(() => documentDetails.value?.content?.trim());
+const documentContentLength = computed(
+  () => documentContent.value?.length || 0
+);
+const isPdf = computed(() => documentDetails.value?.pdf_document);
+const displayUrl = computed(() => documentDetails.value?.display_url);
+const externalLink = computed(() => documentDetails.value?.external_link);
+const sourceHref = computed(() => displayUrl.value || externalLink.value);
+const hasSafeLink = computed(() => isSafeHttpLink(sourceHref.value));
+const displayLink = computed(() => {
+  if (isPdf.value) return formatDocumentLink(externalLink.value);
+  return getDocumentDisplayPath(displayUrl.value || externalLink.value);
+});
+const contentTabLabel = computed(() =>
+  isPdf.value
+    ? t('CAPTAIN.DOCUMENTS.DETAILS.PDF_TAB')
+    : t('CAPTAIN.DOCUMENTS.DETAILS.CONTENT_TAB')
+);
+const tabs = computed(() => [
+  { key: TAB_KEYS.CONTENT, label: contentTabLabel.value },
+  {
+    key: TAB_KEYS.FAQS,
+    label: t('CAPTAIN.DOCUMENTS.RELATED_RESPONSES.TITLE'),
+    count: totalCount.value,
+  },
+]);
+const activeTabKey = computed(() => tabs.value[activeTabIndex.value]?.key);
+const isUnreadableContent = computed(() => {
+  if (!documentContent.value) return false;
+
+  const content = documentContent.value;
+  const sample = content.slice(0, 2000);
+  const characters = Array.from(sample);
+  const nonPrintableCharacters = characters.filter(character => {
+    const charCode = character.charCodeAt(0);
+    return (
+      (charCode <= 31 && ![9, 10, 13].includes(charCode)) ||
+      (charCode >= 127 && charCode <= 159)
+    );
+  });
+  const nonPrintableRatio =
+    nonPrintableCharacters.length / Math.max(characters.length, 1);
+  const replacementCharacterRatio =
+    characters.filter(character => character === '\uFFFD').length /
+    Math.max(characters.length, 1);
+  const hasPdfObjectMarkers =
+    content.includes(' obj') &&
+    content.includes(' endobj') &&
+    content.includes(' stream');
+
+  return (
+    content.startsWith('%PDF') ||
+    hasPdfObjectMarkers ||
+    nonPrintableRatio > 0.02 ||
+    replacementCharacterRatio > 0.05
+  );
+});
+const formattedDocumentContent = computed(() => {
+  if (!documentContent.value || isUnreadableContent.value) return '';
+
+  const formatter = new MessageFormatter(documentContent.value);
+  formatter.disableImageRendering();
+  return formatter.formattedMessage;
+});
+const updatedAtLabel = computed(() => {
+  if (!documentDetails.value?.updated_at) return null;
+  return messageTimestamp(
+    documentDetails.value.updated_at,
+    'MMM d, yyyy h:mm a'
+  );
+});
+const syncedAtLabel = computed(() => {
+  if (!documentDetails.value?.last_synced_at) return null;
+  return messageTimestamp(
+    documentDetails.value.last_synced_at,
+    'MMM d, yyyy h:mm a'
+  );
+});
+
+const handleClose = () => {
+  emit('close');
+};
+
+const handleCopyContent = async () => {
+  try {
+    await copyTextToClipboard(documentContent.value);
+    useAlert(t('CAPTAIN.DOCUMENTS.DETAILS.COPY_SUCCESS'));
+  } catch {
+    useAlert(t('CAPTAIN.DOCUMENTS.DETAILS.COPY_ERROR'));
+  }
+};
+
+const handleTabChanged = tab => {
+  activeTabIndex.value = tabs.value.findIndex(item => item.key === tab.key);
+};
+
+const fetchResponses = (page = 1) => {
+  return store.dispatch('captainResponses/get', {
+    page,
+    assistantId: props.captainDocument.assistant.id,
+    documentId: props.captainDocument.id,
+  });
+};
+
+const handlePageChange = page => {
+  fetchResponses(page);
+};
+
+onMounted(() => {
+  fetchResponses();
+});
+defineExpose({ dialogRef });
+</script>
+
+<template>
+  <Dialog
+    ref="dialogRef"
+    type="edit"
+    :title="documentDetails.name || documentDetails.external_link"
+    :description="t('CAPTAIN.DOCUMENTS.DETAILS.DESCRIPTION')"
+    :show-cancel-button="false"
+    :show-confirm-button="false"
+    overflow-y-auto
+    width="3xl"
+    @close="handleClose"
+  >
+    <div
+      v-if="isFetching"
+      class="flex items-center justify-center py-10 text-n-slate-11"
+    >
+      <Spinner />
+    </div>
+    <div v-else class="flex flex-col gap-6 min-h-48">
+      <section class="flex flex-col gap-3">
+        <div class="grid grid-cols-1 gap-3 sm:grid-cols-3">
+          <div class="flex flex-col gap-1">
+            <span class="text-xs font-medium uppercase text-n-slate-10">
+              {{ t('CAPTAIN.DOCUMENTS.DETAILS.SOURCE') }}
+            </span>
+            <a
+              v-if="hasSafeLink"
+              :href="sourceHref"
+              :title="sourceHref"
+              target="_blank"
+              rel="noopener noreferrer"
+              class="inline-flex items-center min-w-0 gap-1 text-sm text-n-slate-12 hover:underline"
+            >
+              <Icon icon="i-lucide-external-link" class="size-3 shrink-0" />
+              <span class="truncate">{{ displayLink }}</span>
+            </a>
+            <span v-else class="text-sm truncate text-n-slate-12">
+              {{ displayLink }}
+            </span>
+          </div>
+          <div class="flex flex-col gap-1">
+            <span class="text-xs font-medium uppercase text-n-slate-10">
+              {{ t('CAPTAIN.DOCUMENTS.DETAILS.GENERATED_FAQS') }}
+            </span>
+            <span class="text-sm text-n-slate-12">
+              {{ totalCount }}
+            </span>
+          </div>
+          <div class="flex flex-col gap-1">
+            <span class="text-xs font-medium uppercase text-n-slate-10">
+              {{ t('CAPTAIN.DOCUMENTS.DETAILS.LAST_UPDATED') }}
+            </span>
+            <span class="text-sm text-n-slate-12">
+              {{
+                syncedAtLabel ||
+                updatedAtLabel ||
+                t('CAPTAIN.DOCUMENTS.DETAILS.NOT_AVAILABLE')
+              }}
+            </span>
+          </div>
+        </div>
+      </section>
+
+      <TabBar
+        :tabs="tabs"
+        :initial-active-tab="activeTabIndex"
+        @tab-changed="handleTabChanged"
+      />
+
+      <div class="h-[32rem] overflow-y-auto">
+        <section
+          v-if="activeTabKey === TAB_KEYS.CONTENT"
+          class="flex flex-col gap-3"
+        >
+          <div class="flex flex-wrap items-start justify-between gap-3">
+            <div class="flex flex-col gap-1">
+              <h4 class="text-sm font-medium text-n-slate-12">
+                {{
+                  isPdf
+                    ? t('CAPTAIN.DOCUMENTS.DETAILS.PDF_TITLE')
+                    : t('CAPTAIN.DOCUMENTS.DETAILS.CONTENT_TITLE')
+                }}
+              </h4>
+              <span
+                v-if="documentContent && !isPdf"
+                class="text-xs text-n-slate-10"
+              >
+                {{
+                  t('CAPTAIN.DOCUMENTS.DETAILS.CHARACTER_COUNT', {
+                    count: documentContentLength.toLocaleString(),
+                  })
+                }}
+              </span>
+            </div>
+            <div
+              v-if="documentContent && !isPdf"
+              class="flex flex-wrap items-center justify-end gap-4"
+            >
+              <Button
+                :label="
+                  showRawContent
+                    ? t('CAPTAIN.DOCUMENTS.DETAILS.VIEW_PREVIEW')
+                    : t('CAPTAIN.DOCUMENTS.DETAILS.VIEW_RAW')
+                "
+                sm
+                slate
+                link
+                @click="showRawContent = !showRawContent"
+              />
+              <Button
+                :label="t('CAPTAIN.DOCUMENTS.DETAILS.COPY_CONTENT')"
+                icon="i-lucide-copy"
+                sm
+                slate
+                link
+                @click="handleCopyContent"
+              />
+            </div>
+          </div>
+          <div
+            v-if="isPdf"
+            class="rounded-lg border border-n-weak bg-n-alpha-1 p-4 text-sm text-n-slate-11"
+          >
+            <p class="mb-3">
+              {{ t('CAPTAIN.DOCUMENTS.DETAILS.PDF_DESCRIPTION') }}
+            </p>
+            <a
+              v-if="hasSafeLink"
+              :href="sourceHref"
+              :title="sourceHref"
+              target="_blank"
+              rel="noopener noreferrer"
+              class="inline-flex items-center gap-1 font-medium text-n-blue-11 hover:underline"
+            >
+              <Icon icon="i-ph-file-pdf" class="size-4" />
+              {{ displayLink }}
+              <Icon icon="i-lucide-external-link" class="size-3" />
+            </a>
+            <span v-else class="inline-flex items-center gap-1 text-n-slate-12">
+              <Icon icon="i-ph-file-pdf" class="size-4" />
+              {{ displayLink }}
+            </span>
+          </div>
+          <template v-else-if="documentContent">
+            <div
+              v-if="isUnreadableContent && !showRawContent"
+              class="rounded-lg border border-dashed border-n-weak p-4 text-sm text-n-slate-11"
+            >
+              {{ t('CAPTAIN.DOCUMENTS.DETAILS.UNREADABLE_CONTENT') }}
+            </div>
+            <div
+              v-else
+              class="h-[26rem] overflow-y-auto rounded-lg border border-n-weak bg-n-alpha-1 p-4"
+            >
+              <pre
+                v-if="showRawContent || isUnreadableContent"
+                class="m-0 whitespace-pre-wrap break-words text-xs leading-5 text-n-slate-12"
+              ><code>{{ documentContent }}</code></pre>
+              <div
+                v-else
+                v-dompurify-html="formattedDocumentContent"
+                class="prose prose-sm max-w-none break-words text-n-slate-12 prose-p:my-2 prose-headings:mb-2 prose-headings:mt-4 prose-a:text-n-blue-11 prose-ul:my-2 prose-ol:my-2 prose-li:my-1 prose-img:hidden"
+              />
+            </div>
+          </template>
+          <div
+            v-else
+            class="rounded-lg border border-dashed border-n-weak p-4 text-sm text-n-slate-11"
+          >
+            {{ t('CAPTAIN.DOCUMENTS.DETAILS.EMPTY_CONTENT') }}
+          </div>
+        </section>
+
+        <section
+          v-if="activeTabKey === TAB_KEYS.FAQS"
+          class="flex flex-col gap-3"
+        >
+          <div v-if="responses.length" class="flex flex-col gap-3">
+            <ResponseCard
+              v-for="response in responses"
+              :id="response.id"
+              :key="response.id"
+              :question="response.question"
+              :status="response.status"
+              :answer="response.answer"
+              :assistant="response.assistant"
+              :created-at="response.created_at"
+              :updated-at="response.updated_at"
+              compact
+            />
+          </div>
+          <div
+            v-else
+            class="rounded-lg border border-dashed border-n-weak p-4 text-sm text-n-slate-11"
+          >
+            {{ t('CAPTAIN.DOCUMENTS.RELATED_RESPONSES.EMPTY') }}
+          </div>
+          <footer v-if="showPaginationFooter" class="sticky bottom-0 z-10">
+            <PaginationFooter
+              :current-page="currentPage"
+              :total-items="totalCount"
+              :items-per-page="RESPONSES_PER_PAGE"
+              class="!px-0"
+              @update:current-page="handlePageChange"
+            />
+          </footer>
+        </section>
+      </div>
+    </div>
+  </Dialog>
+</template>
diff --git a/app/javascript/dashboard/components-next/captain/pageComponents/document/RelatedResponses.vue b/app/javascript/dashboard/components-next/captain/pageComponents/document/RelatedResponses.vue
deleted file mode 100644
index 9c95fd2b4..000000000
--- a/app/javascript/dashboard/components-next/captain/pageComponents/document/RelatedResponses.vue
+++ /dev/null
@@ -1,71 +0,0 @@
-<script setup>
-import { ref, computed, onMounted } from 'vue';
-import { useStore, useMapGetter } from 'dashboard/composables/store';
-import { useI18n } from 'vue-i18n';
-import Spinner from 'dashboard/components-next/spinner/Spinner.vue';
-import Dialog from 'dashboard/components-next/dialog/Dialog.vue';
-import ResponseCard from '../../assistant/ResponseCard.vue';
-const props = defineProps({
-  captainDocument: {
-    type: Object,
-    required: true,
-  },
-});
-const emit = defineEmits(['close']);
-const { t } = useI18n();
-const store = useStore();
-const dialogRef = ref(null);
-
-const uiFlags = useMapGetter('captainResponses/getUIFlags');
-const responses = useMapGetter('captainResponses/getRecords');
-const meta = useMapGetter('captainResponses/getMeta');
-const isFetching = computed(() => uiFlags.value.fetchingList);
-const totalCount = computed(() => meta.value.totalCount || 0);
-
-const handleClose = () => {
-  emit('close');
-};
-
-onMounted(() => {
-  store.dispatch('captainResponses/get', {
-    assistantId: props.captainDocument.assistant.id,
-    documentId: props.captainDocument.id,
-  });
-});
-defineExpose({ dialogRef });
-</script>
-
-<template>
-  <Dialog
-    ref="dialogRef"
-    type="edit"
-    :title="`${t('CAPTAIN.DOCUMENTS.RELATED_RESPONSES.TITLE')} (${totalCount})`"
-    :description="t('CAPTAIN.DOCUMENTS.RELATED_RESPONSES.DESCRIPTION')"
-    :show-cancel-button="false"
-    :show-confirm-button="false"
-    overflow-y-auto
-    width="3xl"
-    @close="handleClose"
-  >
-    <div
-      v-if="isFetching"
-      class="flex items-center justify-center py-10 text-n-slate-11"
-    >
-      <Spinner />
-    </div>
-    <div v-else class="flex flex-col gap-3 min-h-48">
-      <ResponseCard
-        v-for="response in responses"
-        :id="response.id"
-        :key="response.id"
-        :question="response.question"
-        :status="response.status"
-        :answer="response.answer"
-        :assistant="response.assistant"
-        :created-at="response.created_at"
-        :updated-at="response.updated_at"
-        compact
-      />
-    </div>
-  </Dialog>
-</template>
diff --git a/app/javascript/dashboard/components/widgets/conversation/ReplyBox.vue b/app/javascript/dashboard/components/widgets/conversation/ReplyBox.vue
index 471d10f3c..bd72d45f3 100644
--- a/app/javascript/dashboard/components/widgets/conversation/ReplyBox.vue
+++ b/app/javascript/dashboard/components/widgets/conversation/ReplyBox.vue
@@ -146,6 +146,7 @@ export default {
       currentUser: 'getCurrentUser',
       lastEmail: 'getLastEmailInSelectedChat',
       globalConfig: 'globalConfig/get',
+      isOnChatwootCloud: 'globalConfig/isOnChatwootCloud',
     }),
     currentContact() {
       const senderId = this.currentChat?.meta?.sender?.id;
@@ -173,6 +174,9 @@ export default {
       return this.isATwilioWhatsAppChannel && !this.isPrivate;
     },
     isPrivate() {
+      if (this.isInstagramReplyRestricted) {
+        return true;
+      }
       if (
         this.currentChat.can_reply ||
         this.isAWhatsAppChannel ||
@@ -197,10 +201,16 @@ export default {
       );
       return !!stripped.trim();
     },
+    // Instagram replies are disabled on Chatwoot Cloud during the temporary
+    // Meta platform restriction; private notes remain available.
+    isInstagramReplyRestricted() {
+      return this.isOnChatwootCloud && this.isAnInstagramChannel;
+    },
     isReplyRestricted() {
       return (
-        !this.currentChat?.can_reply &&
-        !(this.isAWhatsAppChannel || this.isAPIInbox)
+        this.isInstagramReplyRestricted ||
+        (!this.currentChat?.can_reply &&
+          !(this.isAWhatsAppChannel || this.isAPIInbox))
       );
     },
     inboxId() {
@@ -470,7 +480,10 @@ export default {
         return;
       }
 
-      if (canReply || this.isAWhatsAppChannel || this.isAPIInbox) {
+      if (
+        !this.isInstagramReplyRestricted &&
+        (canReply || this.isAWhatsAppChannel || this.isAPIInbox)
+      ) {
         this.replyType = REPLY_EDITOR_MODES.REPLY;
       } else {
         this.replyType = REPLY_EDITOR_MODES.NOTE;
@@ -937,7 +950,10 @@ export default {
       this.$store.dispatch('draftMessages/setReplyEditorMode', {
         mode,
       });
-      if (canReply || this.isAWhatsAppChannel || this.isAPIInbox)
+      if (
+        !this.isInstagramReplyRestricted &&
+        (canReply || this.isAWhatsAppChannel || this.isAPIInbox)
+      )
         this.replyType = mode;
       if (this.isRecordingAudio) {
         this.toggleAudioRecorder();
diff --git a/app/javascript/dashboard/i18n/locale/en/integrations.json b/app/javascript/dashboard/i18n/locale/en/integrations.json
index d3dc538a9..629dbd27c 100644
--- a/app/javascript/dashboard/i18n/locale/en/integrations.json
+++ b/app/javascript/dashboard/i18n/locale/en/integrations.json
@@ -811,6 +811,7 @@
     "DOCUMENTS": {
       "HEADER": "Documents",
       "ADD_NEW": "Create a new document",
+      "FAQ_COUNT": "{n} FAQ | {n} FAQs",
       "SELECTED": "{count} selected",
       "SELECT_ALL": "Select all ({count})",
       "UNSELECT_ALL": "Unselect all ({count})",
@@ -870,7 +871,27 @@
       },
       "RELATED_RESPONSES": {
         "TITLE": "Related FAQs",
-        "DESCRIPTION": "These FAQs are generated directly from the document."
+        "EMPTY": "No FAQs have been generated from this document yet."
+      },
+      "DETAILS": {
+        "DESCRIPTION": "Review the crawled content and the FAQs generated from this source.",
+        "SOURCE": "Source",
+        "GENERATED_FAQS": "Generated FAQs",
+        "LAST_UPDATED": "Last updated",
+        "NOT_AVAILABLE": "Not available",
+        "CONTENT_TAB": "Crawled content",
+        "PDF_TAB": "PDF details",
+        "CONTENT_TITLE": "Crawled content",
+        "PDF_TITLE": "PDF file",
+        "PDF_DESCRIPTION": "Review the original PDF source.",
+        "CHARACTER_COUNT": "{count} characters extracted",
+        "COPY_CONTENT": "Copy",
+        "COPY_SUCCESS": "Crawled content copied to clipboard",
+        "COPY_ERROR": "Could not copy crawled content",
+        "VIEW_RAW": "View raw",
+        "VIEW_PREVIEW": "View preview",
+        "UNREADABLE_CONTENT": "Readable content could not be extracted from this document. You can view the raw extracted content.",
+        "EMPTY_CONTENT": "No crawled content is available for this document yet."
       },
       "FORM_DESCRIPTION": "Enter the URL of the document to add it as a knowledge source and choose the assistant to associate it with.",
       "CREATE": {
@@ -911,7 +932,7 @@
       },
 
       "OPTIONS": {
-        "VIEW_RELATED_RESPONSES": "View Related Responses",
+        "VIEW_DETAILS": "View details",
         "SYNC_NOW": "Refresh now",
         "RETRY_SYNC": "Retry refresh",
         "DELETE_DOCUMENT": "Delete Document"
diff --git a/app/javascript/dashboard/routes/dashboard/captain/documents/Index.vue b/app/javascript/dashboard/routes/dashboard/captain/documents/Index.vue
index 87c04aefe..9c1effd20 100644
--- a/app/javascript/dashboard/routes/dashboard/captain/documents/Index.vue
+++ b/app/javascript/dashboard/routes/dashboard/captain/documents/Index.vue
@@ -17,7 +17,7 @@ import Input from 'dashboard/components-next/input/Input.vue';
 import Policy from 'dashboard/components/policy.vue';
 import PageLayout from 'dashboard/components-next/captain/PageLayout.vue';
 import CaptainPaywall from 'dashboard/components-next/captain/pageComponents/Paywall.vue';
-import RelatedResponses from 'dashboard/components-next/captain/pageComponents/document/RelatedResponses.vue';
+import DocumentDetails from 'dashboard/components-next/captain/pageComponents/document/DocumentDetails.vue';
 import CreateDocumentDialog from 'dashboard/components-next/captain/pageComponents/document/CreateDocumentDialog.vue';
 import DocumentPageEmptyState from 'dashboard/components-next/captain/pageComponents/emptyStates/DocumentPageEmptyState.vue';
 import FeatureSpotlightPopover from 'dashboard/components-next/feature-spotlight/FeatureSpotlightPopover.vue';
@@ -51,22 +51,22 @@ const handleDelete = () => {
   deleteDocumentDialog.value.dialogRef.open();
 };
 
-const showRelatedResponses = ref(false);
+const showDocumentDetails = ref(false);
 const showCreateDialog = ref(false);
 const createDocumentDialog = ref(null);
-const relationQuestionDialog = ref(null);
+const documentDetailsDialog = ref(null);
 
-const handleShowRelatedDocument = () => {
-  showRelatedResponses.value = true;
-  nextTick(() => relationQuestionDialog.value.dialogRef.open());
+const handleShowDocumentDetails = () => {
+  showDocumentDetails.value = true;
+  nextTick(() => documentDetailsDialog.value.dialogRef.open());
 };
 const handleCreateDocument = () => {
   showCreateDialog.value = true;
   nextTick(() => createDocumentDialog.value.dialogRef.open());
 };
 
-const handleRelatedResponseClose = () => {
-  showRelatedResponses.value = false;
+const handleDocumentDetailsClose = () => {
+  showDocumentDetails.value = false;
 };
 
 const handleCreateDialogClose = () => {
@@ -235,8 +235,8 @@ const handleAction = ({ action, id }) => {
   nextTick(() => {
     if (action === 'delete') {
       handleDelete();
-    } else if (action === 'viewRelatedQuestions') {
-      handleShowRelatedDocument();
+    } else if (action === 'viewDetails') {
+      handleShowDocumentDetails();
     } else if (action === 'sync') {
       handleSync(id);
     }
@@ -416,6 +416,7 @@ onUnmounted(() => {
           :last-sync-error-code="doc.last_sync_error_code"
           :sync-in-progress="doc.sync_in_progress"
           :sync-stale-after-hours="syncIntervalHours"
+          :responses-count="doc.responses_count"
           :is-selected="canManageDocuments && bulkSelectedIds.has(doc.id)"
           :selectable="canManageDocuments"
           :show-selection-control="shouldShowSelectionControl(doc.id)"
@@ -427,11 +428,11 @@ onUnmounted(() => {
       </div>
     </template>
 
-    <RelatedResponses
-      v-if="showRelatedResponses"
-      ref="relationQuestionDialog"
+    <DocumentDetails
+      v-if="showDocumentDetails"
+      ref="documentDetailsDialog"
       :captain-document="selectedDocument"
-      @close="handleRelatedResponseClose"
+      @close="handleDocumentDetailsClose"
     />
     <CreateDocumentDialog
       v-if="showCreateDialog"
diff --git a/app/javascript/shared/helpers/MessageFormatter.js b/app/javascript/shared/helpers/MessageFormatter.js
index 85ce67bc6..1a14266f0 100644
--- a/app/javascript/shared/helpers/MessageFormatter.js
+++ b/app/javascript/shared/helpers/MessageFormatter.js
@@ -104,6 +104,11 @@ class MessageFormatter {
     return this.md.render(updatedMessage);
   }
 
+  disableImageRendering() {
+    this.md.disable(['add-image-sizing']);
+    this.md.renderer.rules.image = () => '';
+  }
+
   get formattedMessage() {
     return this.formatMessage();
   }
diff --git a/app/javascript/shared/helpers/specs/MessageFormatter.spec.js b/app/javascript/shared/helpers/specs/MessageFormatter.spec.js
index 3350399eb..20d64005a 100644
--- a/app/javascript/shared/helpers/specs/MessageFormatter.spec.js
+++ b/app/javascript/shared/helpers/specs/MessageFormatter.spec.js
@@ -68,6 +68,25 @@ describe('#MessageFormatter', () => {
     });
   });
 
+  describe('#disableImageRendering', () => {
+    it('omits nested and reference images with relative URLs', () => {
+      const message = `Before ![nested [alt]](/relative.png)
+
+![reference][logo]
+
+[logo]: /logo.png
+
+After`;
+      const formatter = new MessageFormatter(message);
+
+      formatter.disableImageRendering();
+
+      expect(formatter.formattedMessage).not.toContain('<img');
+      expect(formatter.formattedMessage).toContain('Before');
+      expect(formatter.formattedMessage).toContain('After');
+    });
+  });
+
   describe('tweets', () => {
     it('should return the same string if not tags or @mentions', () => {
       const message = 'Chatwoot is an opensource tool';
diff --git a/app/services/imap/base_fetch_email_service.rb b/app/services/imap/base_fetch_email_service.rb
index e55355f3a..9c5b8e27b 100644
--- a/app/services/imap/base_fetch_email_service.rb
+++ b/app/services/imap/base_fetch_email_service.rb
@@ -38,7 +38,8 @@ class Imap::BaseFetchEmailService
   end
 
   def email_already_present?(channel, message_id)
-    channel.inbox.messages.find_by(source_id: message_id).present? || deleted_message_tracker.deleted?(message_id)
+    # exists? avoids Message's default_scope ORDER BY, which full-scans large inboxes
+    channel.inbox.messages.exists?(source_id: message_id) || deleted_message_tracker.deleted?(message_id)
   end
 
   def deleted_message_tracker
diff --git a/app/services/whatsapp/providers/whatsapp_cloud_service.rb b/app/services/whatsapp/providers/whatsapp_cloud_service.rb
index 69631c468..373e47b3c 100644
--- a/app/services/whatsapp/providers/whatsapp_cloud_service.rb
+++ b/app/services/whatsapp/providers/whatsapp_cloud_service.rb
@@ -40,7 +40,11 @@ class Whatsapp::Providers::WhatsappCloudService < Whatsapp::Providers::BaseServi
 
   def fetch_whatsapp_templates(url)
     response = HTTParty.get(url)
-    return [] unless response.success?
+    unless response.success?
+      Rails.logger.warn "[WHATSAPP] Template sync failed for account #{whatsapp_channel.account_id} " \
+                        "inbox #{whatsapp_channel.inbox&.id}: #{response.code} #{error_message(response)}"
+      return []
+    end
 
     next_url = next_url(response)
 
@@ -155,7 +159,7 @@ class Whatsapp::Providers::WhatsappCloudService < Whatsapp::Providers::BaseServi
 
   def error_message(response)
     # https://developers.facebook.com/docs/whatsapp/cloud-api/support/error-codes/#sample-response
-    response.parsed_response&.dig('error', 'message')
+    response.parsed_response.dig('error', 'message') if response.parsed_response.is_a?(Hash)
   end
 
   def voice_message?(type, attachment)
diff --git a/app/services/whatsapp/webhook_teardown_service.rb b/app/services/whatsapp/webhook_teardown_service.rb
index 948d84f04..de794f8e3 100644
--- a/app/services/whatsapp/webhook_teardown_service.rb
+++ b/app/services/whatsapp/webhook_teardown_service.rb
@@ -23,7 +23,6 @@ class Whatsapp::WebhookTeardownService
 
   def should_teardown_webhook?
     @channel.provider == 'whatsapp_cloud' &&
-      provider_config['source'] == 'embedded_signup' &&
       provider_config['api_key'].present? &&
       (provider_config['phone_number_id'].present? || provider_config['business_account_id'].present?)
   end
@@ -38,8 +37,11 @@ class Whatsapp::WebhookTeardownService
     Rails.logger.error "[WHATSAPP] Phone-level webhook clear failed for channel #{@channel.id}: #{e.message}"
   end
 
-  # The app subscription is shared by every inbox on the WABA, so only unsubscribe when this is the last one.
+  # Embedded signup only — a manual token's subscribed app is the customer's, not ours to unsubscribe.
+  # The subscription is shared across the WABA, so only unsubscribe when this is the last inbox.
   def unsubscribe_app_if_last_inbox(api_client)
+    return unless provider_config['source'] == 'embedded_signup'
+
     waba_id = provider_config['business_account_id']
     return if waba_id.blank?
     return if waba_sibling_exists?(waba_id)
diff --git a/db/migrate/20260709091147_create_agent_sessions.rb b/db/migrate/20260709091147_create_agent_sessions.rb
new file mode 100644
index 000000000..a2e3e9f0f
--- /dev/null
+++ b/db/migrate/20260709091147_create_agent_sessions.rb
@@ -0,0 +1,24 @@
+class CreateAgentSessions < ActiveRecord::Migration[7.1]
+  def change
+    create_table :agent_sessions do |t|
+      t.integer :session_type, null: false
+      t.references :subject, polymorphic: true, null: false, index: false
+      t.references :result, polymorphic: true, index: false
+      t.references :account, null: false, index: true
+      t.references :assistant, null: false, index: true
+      t.references :user, index: true
+      t.string :llm_model
+      t.float :credits_consumed
+      t.jsonb :faq_ids, default: []
+      t.jsonb :document_ids, default: []
+      t.jsonb :scenario_ids, default: []
+      t.jsonb :run_context, default: {}
+
+      t.timestamps
+    end
+
+    add_index :agent_sessions, [:account_id, :session_type, :created_at]
+    add_index :agent_sessions, [:account_id, :subject_type, :subject_id]
+    add_index :agent_sessions, [:account_id, :result_type, :result_id]
+  end
+end
diff --git a/db/migrate/20260713184351_create_captain_faq_suggestions.rb b/db/migrate/20260713184351_create_captain_faq_suggestions.rb
new file mode 100644
index 000000000..6bc03f387
--- /dev/null
+++ b/db/migrate/20260713184351_create_captain_faq_suggestions.rb
@@ -0,0 +1,48 @@
+class CreateCaptainFaqSuggestions < ActiveRecord::Migration[7.1]
+  def change
+    create_faq_suggestions
+    create_faq_observations
+  end
+
+  private
+
+  def create_faq_suggestions
+    create_table :captain_faq_suggestions do |t|
+      t.string :question, null: false
+      t.text :answer, null: false
+      t.vector :embedding, limit: 1536
+      t.references :assistant, null: false, index: true
+      t.references :account, null: false, index: true
+      t.string :language, null: false, default: 'en'
+      t.integer :source_count, null: false, default: 0
+      t.integer :status, null: false, default: 0
+
+      t.timestamps
+    end
+
+    add_index :captain_faq_suggestions, [:account_id, :assistant_id, :status, :language],
+              name: 'idx_cap_faq_suggestions_on_account_assistant_status_language'
+    add_index :captain_faq_suggestions, :embedding, using: :ivfflat,
+                                                    name: 'vector_idx_captain_faq_suggestions_embedding',
+                                                    opclass: :vector_cosine_ops
+  end
+
+  def create_faq_observations
+    create_table :captain_faq_observations do |t|
+      t.references :account, null: false, index: true
+      t.references :conversation, null: false, index: true
+      t.references :faq_suggestion, index: true
+      t.string :generated_question, null: false
+      t.text :generated_answer, null: false
+      t.string :language, null: false, default: 'en'
+      t.integer :status, null: false, default: 0
+
+      t.timestamps
+    end
+
+    add_index :captain_faq_observations, [:conversation_id, :faq_suggestion_id],
+              unique: true,
+              where: 'faq_suggestion_id IS NOT NULL',
+              name: 'idx_captain_faq_observations_on_conversation_and_suggestion'
+  end
+end
diff --git a/db/schema.rb b/db/schema.rb
index e01dc34c1..43e7135b9 100644
--- a/db/schema.rb
+++ b/db/schema.rb
@@ -10,7 +10,7 @@
 #
 # It's strongly recommended that you check this file into your version control system.
 
-ActiveRecord::Schema[7.1].define(version: 2026_07_10_000000) do
+ActiveRecord::Schema[7.1].define(version: 2026_07_13_184351) do
   # These extensions should be enabled to support this database
   enable_extension "pg_stat_statements"
   enable_extension "pg_trgm"
@@ -146,6 +146,31 @@ ActiveRecord::Schema[7.1].define(version: 2026_07_10_000000) do
     t.index ["account_id"], name: "index_agent_capacity_policies_on_account_id"
   end
 
+  create_table "agent_sessions", force: :cascade do |t|
+    t.integer "session_type", null: false
+    t.string "subject_type", null: false
+    t.bigint "subject_id", null: false
+    t.string "result_type"
+    t.bigint "result_id"
+    t.bigint "account_id", null: false
+    t.bigint "assistant_id", null: false
+    t.bigint "user_id"
+    t.string "llm_model"
+    t.float "credits_consumed"
+    t.jsonb "faq_ids", default: []
+    t.jsonb "document_ids", default: []
+    t.jsonb "scenario_ids", default: []
+    t.jsonb "run_context", default: {}
+    t.datetime "created_at", null: false
+    t.datetime "updated_at", null: false
+    t.index ["account_id", "result_type", "result_id"], name: "idx_on_account_id_result_type_result_id_ca66c00cd7"
+    t.index ["account_id", "session_type", "created_at"], name: "idx_on_account_id_session_type_created_at_c20a14bd4e"
+    t.index ["account_id", "subject_type", "subject_id"], name: "idx_on_account_id_subject_type_subject_id_6d60963b3d"
+    t.index ["account_id"], name: "index_agent_sessions_on_account_id"
+    t.index ["assistant_id"], name: "index_agent_sessions_on_assistant_id"
+    t.index ["user_id"], name: "index_agent_sessions_on_user_id"
+  end
+
   create_table "applied_slas", force: :cascade do |t|
     t.bigint "account_id", null: false
     t.bigint "sla_policy_id", null: false
@@ -392,6 +417,39 @@ ActiveRecord::Schema[7.1].define(version: 2026_07_10_000000) do
     t.index ["status"], name: "index_captain_documents_on_status"
   end
 
+  create_table "captain_faq_observations", force: :cascade do |t|
+    t.bigint "account_id", null: false
+    t.bigint "conversation_id", null: false
+    t.bigint "faq_suggestion_id"
+    t.string "generated_question", null: false
+    t.text "generated_answer", null: false
+    t.string "language", default: "en", null: false
+    t.integer "status", default: 0, null: false
+    t.datetime "created_at", null: false
+    t.datetime "updated_at", null: false
+    t.index ["account_id"], name: "index_captain_faq_observations_on_account_id"
+    t.index ["conversation_id", "faq_suggestion_id"], name: "idx_captain_faq_observations_on_conversation_and_suggestion", unique: true, where: "(faq_suggestion_id IS NOT NULL)"
+    t.index ["conversation_id"], name: "index_captain_faq_observations_on_conversation_id"
+    t.index ["faq_suggestion_id"], name: "index_captain_faq_observations_on_faq_suggestion_id"
+  end
+
+  create_table "captain_faq_suggestions", force: :cascade do |t|
+    t.string "question", null: false
+    t.text "answer", null: false
+    t.vector "embedding", limit: 1536
+    t.bigint "assistant_id", null: false
+    t.bigint "account_id", null: false
+    t.string "language", default: "en", null: false
+    t.integer "source_count", default: 0, null: false
+    t.integer "status", default: 0, null: false
+    t.datetime "created_at", null: false
+    t.datetime "updated_at", null: false
+    t.index ["account_id"], name: "index_captain_faq_suggestions_on_account_id"
+    t.index ["account_id", "assistant_id", "status", "language"], name: "idx_cap_faq_suggestions_on_account_assistant_status_language"
+    t.index ["assistant_id"], name: "index_captain_faq_suggestions_on_assistant_id"
+    t.index ["embedding"], name: "vector_idx_captain_faq_suggestions_embedding", opclass: :vector_cosine_ops, using: :ivfflat
+  end
+
   create_table "captain_inboxes", force: :cascade do |t|
     t.bigint "captain_assistant_id", null: false
     t.bigint "inbox_id", null: false
diff --git a/enterprise/app/controllers/api/v1/accounts/captain/documents_controller.rb b/enterprise/app/controllers/api/v1/accounts/captain/documents_controller.rb
index 273c082b1..d88cc6b48 100644
--- a/enterprise/app/controllers/api/v1/accounts/captain/documents_controller.rb
+++ b/enterprise/app/controllers/api/v1/accounts/captain/documents_controller.rb
@@ -9,16 +9,10 @@ class Api::V1::Accounts::Captain::DocumentsController < Api::V1::Accounts::BaseC
   RESULTS_PER_PAGE = 25
 
   def index
-    base_query = @documents
-    base_query = base_query.where(assistant_id: permitted_params[:assistant_id]) if permitted_params[:assistant_id].present?
-    base_query = apply_source_filter(base_query, permitted_params[:source])
-    base_query = apply_filter(base_query, permitted_params[:filter])
-    base_query = apply_search(base_query, permitted_params[:search_key])
-    base_query = apply_sort(base_query, permitted_params[:sort])
-
-    @documents_count = base_query.count
+    @documents = filtered_documents
+    @documents_count = @documents.count
     @sync_interval_hours = current_sync_interval&.in_hours&.to_i
-    @documents = base_query.page(@current_page).per(RESULTS_PER_PAGE)
+    @documents = with_responses_count(@documents).page(@current_page).per(RESULTS_PER_PAGE)
   end
 
   def show; end
@@ -59,6 +53,21 @@ class Api::V1::Accounts::Captain::DocumentsController < Api::V1::Accounts::BaseC
     @documents = Current.account.captain_documents.with_attached_pdf_file.includes(:assistant)
   end
 
+  def filtered_documents
+    documents = @documents
+    documents = documents.where(assistant_id: permitted_params[:assistant_id]) if permitted_params[:assistant_id].present?
+    documents = apply_source_filter(documents, permitted_params[:source])
+    documents = apply_filter(documents, permitted_params[:filter])
+    documents = apply_search(documents, permitted_params[:search_key])
+    apply_sort(documents, permitted_params[:sort])
+  end
+
+  def with_responses_count(scope)
+    scope.left_joins(:responses)
+         .select('captain_documents.*, COUNT(captain_assistant_responses.id) AS responses_count')
+         .group('captain_documents.id')
+  end
+
   def set_document
     @document = @documents.find(permitted_params[:id])
   end
diff --git a/enterprise/app/models/captain/agent_session.rb b/enterprise/app/models/captain/agent_session.rb
new file mode 100644
index 000000000..d02dffcab
--- /dev/null
+++ b/enterprise/app/models/captain/agent_session.rb
@@ -0,0 +1,86 @@
+# == Schema Information
+#
+# Table name: agent_sessions
+#
+#  id               :bigint           not null, primary key
+#  credits_consumed :float
+#  document_ids     :jsonb
+#  faq_ids          :jsonb
+#  llm_model        :string
+#  result_type      :string
+#  run_context      :jsonb
+#  scenario_ids     :jsonb
+#  session_type     :integer          not null
+#  subject_type     :string           not null
+#  created_at       :datetime         not null
+#  updated_at       :datetime         not null
+#  account_id       :bigint           not null
+#  assistant_id     :bigint           not null
+#  result_id        :bigint
+#  subject_id       :bigint           not null
+#  user_id          :bigint
+#
+# Indexes
+#
+#  idx_on_account_id_result_type_result_id_ca66c00cd7    (account_id,result_type,result_id)
+#  idx_on_account_id_session_type_created_at_c20a14bd4e  (account_id,session_type,created_at)
+#  idx_on_account_id_subject_type_subject_id_6d60963b3d  (account_id,subject_type,subject_id)
+#  index_agent_sessions_on_account_id                    (account_id)
+#  index_agent_sessions_on_assistant_id                  (assistant_id)
+#  index_agent_sessions_on_user_id                       (user_id)
+#
+class Captain::AgentSession < ApplicationRecord
+  self.table_name = 'agent_sessions'
+
+  SUBJECT_TYPES = { 'assistant' => 'Conversation', 'copilot' => 'CopilotThread' }.freeze
+  RESULT_TYPES = { 'assistant' => 'Message', 'copilot' => 'CopilotMessage' }.freeze
+
+  belongs_to :account
+  belongs_to :assistant, class_name: 'Captain::Assistant'
+  belongs_to :user, optional: true
+  belongs_to :subject, ->(session) { where(account_id: session.account_id) }, polymorphic: true
+  belongs_to :result, ->(session) { where(account_id: session.account_id) }, polymorphic: true, optional: true
+
+  enum :session_type, { assistant: 0, copilot: 1 }, prefix: :session
+
+  before_validation :ensure_account
+
+  validate :subject_type_matches_session_type
+  validate :result_type_matches_session_type, if: -> { result_type.present? }
+  validate :subject_belongs_to_account
+  validate :result_belongs_to_account, if: -> { result_id.present? }
+
+  private
+
+  def ensure_account
+    self.account = assistant&.account
+  end
+
+  def subject_type_matches_session_type
+    expected_type = SUBJECT_TYPES[session_type]
+    return if subject_type == expected_type
+
+    errors.add(:subject_type, "must be #{expected_type} for #{session_type} sessions")
+  end
+
+  def result_type_matches_session_type
+    expected_type = RESULT_TYPES[session_type]
+    return if result_type == expected_type
+
+    errors.add(:result_type, "must be #{expected_type} for #{session_type} sessions")
+  end
+
+  def subject_belongs_to_account
+    return if subject.nil? || subject.account_id == account_id
+
+    errors.add(:subject, 'must belong to the session account')
+  end
+
+  def result_belongs_to_account
+    target_class = result_type.safe_constantize
+    actual_account_id = target_class && target_class.unscoped.where(id: result_id).pick(:account_id)
+    return if actual_account_id == account_id
+
+    errors.add(:result, 'must belong to the session account')
+  end
+end
diff --git a/enterprise/app/models/captain/assistant.rb b/enterprise/app/models/captain/assistant.rb
index d3f6cda8a..bf4691e2c 100644
--- a/enterprise/app/models/captain/assistant.rb
+++ b/enterprise/app/models/captain/assistant.rb
@@ -28,6 +28,7 @@ class Captain::Assistant < ApplicationRecord
   belongs_to :account
   has_many :documents, class_name: 'Captain::Document', dependent: :destroy_async
   has_many :responses, class_name: 'Captain::AssistantResponse', dependent: :destroy_async
+  has_many :faq_suggestions, class_name: 'Captain::FaqSuggestion', dependent: :destroy_async
   has_many :captain_inboxes,
            class_name: 'CaptainInbox',
            foreign_key: :captain_assistant_id,
@@ -37,6 +38,7 @@ class Captain::Assistant < ApplicationRecord
   has_many :messages, as: :sender, dependent: :nullify
   has_many :copilot_threads, dependent: :destroy_async
   has_many :scenarios, class_name: 'Captain::Scenario', dependent: :destroy_async
+  has_many :agent_sessions, class_name: 'Captain::AgentSession', dependent: :destroy_async
 
   store_accessor :config, :temperature, :feature_faq, :feature_memory, :feature_contact_attributes, :product_name
 
diff --git a/enterprise/app/models/captain/faq_observation.rb b/enterprise/app/models/captain/faq_observation.rb
new file mode 100644
index 000000000..15c5e1284
--- /dev/null
+++ b/enterprise/app/models/captain/faq_observation.rb
@@ -0,0 +1,42 @@
+# == Schema Information
+#
+# Table name: captain_faq_observations
+#
+#  id                 :bigint           not null, primary key
+#  generated_answer   :text             not null
+#  generated_question :string           not null
+#  language           :string           default("en"), not null
+#  status             :integer          default("attached"), not null
+#  created_at         :datetime         not null
+#  updated_at         :datetime         not null
+#  account_id         :bigint           not null
+#  conversation_id    :bigint           not null
+#  faq_suggestion_id  :bigint
+#
+class Captain::FaqObservation < ApplicationRecord
+  self.table_name = 'captain_faq_observations'
+
+  belongs_to :account
+  belongs_to :conversation, class_name: '::Conversation'
+  belongs_to :faq_suggestion, class_name: 'Captain::FaqSuggestion', optional: true, inverse_of: :observations
+
+  enum status: { attached: 0, discarded: 1 }
+
+  validates :generated_question, :generated_answer, :language, presence: true
+  validates :faq_suggestion, presence: true, if: :attached?
+  validate :faq_suggestion_belongs_to_account
+
+  before_validation :ensure_account
+
+  private
+
+  def ensure_account
+    self.account = conversation&.account
+  end
+
+  def faq_suggestion_belongs_to_account
+    return if faq_suggestion.blank? || faq_suggestion.account_id == account_id
+
+    errors.add(:faq_suggestion, :invalid)
+  end
+end
diff --git a/enterprise/app/models/captain/faq_suggestion.rb b/enterprise/app/models/captain/faq_suggestion.rb
new file mode 100644
index 000000000..047d5e1fe
--- /dev/null
+++ b/enterprise/app/models/captain/faq_suggestion.rb
@@ -0,0 +1,51 @@
+# == Schema Information
+#
+# Table name: captain_faq_suggestions
+#
+#  id           :bigint           not null, primary key
+#  answer       :text             not null
+#  embedding    :vector(1536)
+#  language     :string           default("en"), not null
+#  question     :string           not null
+#  source_count :integer          default(0), not null
+#  status       :integer          default("open"), not null
+#  created_at   :datetime         not null
+#  updated_at   :datetime         not null
+#  account_id   :bigint           not null
+#  assistant_id :bigint           not null
+#
+class Captain::FaqSuggestion < ApplicationRecord
+  self.table_name = 'captain_faq_suggestions'
+
+  belongs_to :assistant, class_name: 'Captain::Assistant'
+  belongs_to :account
+  has_many :observations,
+           class_name: 'Captain::FaqObservation',
+           dependent: :delete_all,
+           inverse_of: :faq_suggestion
+  has_neighbors :embedding, normalize: true
+
+  enum status: { open: 0, approved: 1, dismissed: 2 }
+
+  validates :question, :answer, :language, presence: true
+
+  before_validation :ensure_account
+  after_commit :update_embedding, on: [:create, :update]
+
+  scope :ordered, -> { order(source_count: :desc, updated_at: :desc) }
+  scope :by_language, ->(language) { where(language: language) }
+
+  private
+
+  def ensure_account
+    self.account = assistant&.account
+  end
+
+  def update_embedding
+    return unless open?
+    return unless saved_change_to_question? || saved_change_to_answer? || embedding.nil?
+    return if previously_new_record? && embedding.present?
+
+    Captain::Llm::UpdateEmbeddingJob.perform_later(self, "#{question}: #{answer}")
+  end
+end
diff --git a/enterprise/app/models/enterprise/concerns/account.rb b/enterprise/app/models/enterprise/concerns/account.rb
index 1ef112fb5..427b1e1af 100644
--- a/enterprise/app/models/enterprise/concerns/account.rb
+++ b/enterprise/app/models/enterprise/concerns/account.rb
@@ -11,8 +11,11 @@ module Enterprise::Concerns::Account
 
     has_many :captain_assistants, dependent: :destroy_async, class_name: 'Captain::Assistant'
     has_many :captain_assistant_responses, dependent: :destroy_async, class_name: 'Captain::AssistantResponse'
+    has_many :captain_faq_observations, dependent: :destroy_async, class_name: 'Captain::FaqObservation'
+    has_many :captain_faq_suggestions, dependent: :destroy_async, class_name: 'Captain::FaqSuggestion'
     has_many :captain_documents, dependent: :destroy_async, class_name: 'Captain::Document'
     has_many :captain_custom_tools, dependent: :destroy_async, class_name: 'Captain::CustomTool'
+    has_many :captain_agent_sessions, dependent: :destroy_async, class_name: 'Captain::AgentSession'
 
     has_many :copilot_threads, dependent: :destroy_async
     has_many :companies, dependent: :destroy_async
diff --git a/enterprise/app/models/enterprise/concerns/conversation.rb b/enterprise/app/models/enterprise/concerns/conversation.rb
index a075704d1..c247e01e8 100644
--- a/enterprise/app/models/enterprise/concerns/conversation.rb
+++ b/enterprise/app/models/enterprise/concerns/conversation.rb
@@ -7,6 +7,7 @@ module Enterprise::Concerns::Conversation
     has_many :sla_events, dependent: :destroy_async
     has_many :calls, dependent: :destroy_async
     has_many :captain_responses, class_name: 'Captain::AssistantResponse', dependent: :nullify, as: :documentable
+    has_many :captain_faq_observations, class_name: 'Captain::FaqObservation', dependent: :delete_all
     scope :with_sla_applicable_contact, -> { left_joins(:contact).where(contacts: { blocked: [false, nil] }) }
 
     before_validation :validate_sla_policy, if: -> { sla_policy_id_changed? }
diff --git a/enterprise/app/views/api/v1/models/captain/_document.json.jbuilder b/enterprise/app/views/api/v1/models/captain/_document.json.jbuilder
index 56260f675..0ab031dbf 100644
--- a/enterprise/app/views/api/v1/models/captain/_document.json.jbuilder
+++ b/enterprise/app/views/api/v1/models/captain/_document.json.jbuilder
@@ -9,6 +9,8 @@ json.external_link resource.external_link
 json.display_url resource.display_url
 json.file_size resource.file_size
 json.pdf_document resource.pdf_document?
+responses_count = resource.respond_to?(:responses_count) ? resource.responses_count : resource.responses.count
+json.responses_count responses_count.to_i
 json.id resource.id
 json.name resource.name
 json.status resource.status
diff --git a/enterprise/lib/captain/conversation_completion_service.rb b/enterprise/lib/captain/conversation_completion_service.rb
index c45559165..37f9add3e 100644
--- a/enterprise/lib/captain/conversation_completion_service.rb
+++ b/enterprise/lib/captain/conversation_completion_service.rb
@@ -12,7 +12,7 @@ class Captain::ConversationCompletionService < Captain::BaseTaskService
   pattr_initialize [:account!, :conversation_display_id!]
 
   def perform
-    content = format_messages_as_string
+    content = format_evaluation_input
     return default_incomplete_response('No messages found') if content.blank?
 
     response = make_api_call(
@@ -35,12 +35,58 @@ class Captain::ConversationCompletionService < Captain::BaseTaskService
     Rails.root.join('enterprise/lib/captain/prompts', "#{file_name}.liquid").read
   end
 
-  def format_messages_as_string
-    messages = conversation_messages(start_from: 0)
-    messages.map do |msg|
-      sender_type = msg[:role] == 'user' ? 'Customer' : 'Assistant'
-      "#{sender_type}: #{msg[:content]}"
+  def format_evaluation_input
+    messages = conversation_message_records(start_from: 0)
+    return if messages.blank?
+
+    [
+      "Conversation status: #{conversation.status}",
+      format_messages_as_string(messages)
+    ].join("\n\n")
+  end
+
+  def conversation_message_records(start_from: 0)
+    messages = []
+    character_count = start_from
+
+    conversation.messages
+                .where(message_type: [:incoming, :outgoing])
+                .where(private: false)
+                .reorder('id desc')
+                .each do |message|
+      content = message.content_for_llm
+      next if content.blank?
+      break if character_count + content.length > TOKEN_LIMIT
+
+      messages.prepend({ message: message, content: content })
+      character_count += content.length
+    end
+
+    messages
+  end
+
+  def format_messages_as_string(messages)
+    transcript = messages.map do |message_context|
+      "#{message_sender_label(message_context[:message])}: #{message_context[:content]}"
     end.join("\n")
+
+    "Conversation transcript:\n#{transcript}"
+  end
+
+  def message_sender_label(message)
+    return 'Customer' if message.incoming?
+    return 'Captain' if captain_reply?(message)
+    return 'Bot' if bot_reply?(message)
+
+    'Assistant'
+  end
+
+  def captain_reply?(message)
+    message.outgoing? && message.sender_type == 'Captain::Assistant'
+  end
+
+  def bot_reply?(message)
+    message.outgoing? && message.sender_type.in?(['AgentBot', 'Captain::Assistant'])
   end
 
   def parse_response(message)
diff --git a/enterprise/lib/captain/prompts/conversation_completion.liquid b/enterprise/lib/captain/prompts/conversation_completion.liquid
index ed81039af..e039f60b0 100644
--- a/enterprise/lib/captain/prompts/conversation_completion.liquid
+++ b/enterprise/lib/captain/prompts/conversation_completion.liquid
@@ -2,18 +2,39 @@ You are evaluating whether a customer support conversation is complete and can b
 
 The conversation may be in any language. Apply these criteria based on the intent and meaning of messages, regardless of language.
 
+You will receive:
+- Conversation status
+- Conversation transcript where messages are labeled as Customer, Captain, Bot, or Assistant
+
+This evaluator runs for inactive pending conversations. Focus on the latest pending exchange or latest unresolved customer request. Older messages may be present only for context.
+If the conversation status is "pending", the conversation is still with Captain. Do not assume a handoff happened because Captain mentioned one.
+
 A conversation is INCOMPLETE (keep open) if ANY of these apply:
 - The assistant asked a question or requested information that the customer hasn't provided
 - The customer asked a question that wasn't fully answered
 - The customer asked for something the assistant couldn't do — even if the assistant explained why, the customer's need is unmet
 - The customer raised multiple questions or issues and not all were addressed
+- In the latest pending exchange, Captain, Bot, or Assistant said it handed off, will hand off, escalated, will escalate, or that a human/team/another party will continue the work
+- In the latest pending exchange, Captain, Bot, or Assistant promised future action or follow-up instead of resolving the customer's request
+- In the latest pending exchange, the customer is waiting for another party's action, response, status update, or investigation result
+- The latest customer message is only an attachment placeholder such as "[Attachment]" and there is no later text explaining what it contains or showing the issue was answered
+- The customer says they were not helped, asks why nobody replied, repeats the unresolved issue after a previous answer, or otherwise indicates dissatisfaction with the current help
+
+Do NOT treat these as incomplete by themselves:
+- A generic greeting or broad optional offer from Captain/Bot/Assistant, such as "How can I help?", "What would you like to know?", or "Anything else?", when the customer has not made a recognizable request
+- A customer greeting, single-word reply, name, phone number, or gibberish with no recognizable question/request, followed only by Captain/Bot/Assistant asking what the customer needs
+- An optional invitation for the customer to ask more questions after the assistant already answered the actual request
+- Older handoff, escalation, or follow-up messages from a previous exchange when the latest customer message starts a new topic, has no recognizable request, or has already been answered
+
+Important handoff rule:
+- A handoff, escalation, transfer, acknowledgement, or promise of future follow-up is not a resolution by itself
+- If conversation status is "pending" and Captain/Bot/Assistant says it handed off, will hand off, or that another party will continue the work in the latest pending exchange, keep the conversation INCOMPLETE.
 
 A conversation is COMPLETE only if ALL of these are true:
 - The assistant's answer fully addressed the customer's question or issue and is self-contained — it requires no further action from the customer
 - There are no unanswered questions, unmet requests, or outstanding follow-ups from either side
 - Note: customers often do not explicitly say thanks or confirm resolution. If the assistant gave a complete, self-contained answer and the customer had no follow-up, that is sufficient. Do not require explicit gratitude or confirmation.
-- If the customer sent only one or two short messages (single words, names, phone numbers, or gibberish) with no recognizable question or request across the entire conversation, and the
-  assistant has responded asking for clarification, the conversation is COMPLETE.
+- If the customer sent only one or two short text messages (greetings, single words, names, phone numbers, or gibberish) with no recognizable question or request across the entire conversation, and Captain/Bot/Assistant has responded asking what they need or offering help, the conversation is COMPLETE.
 
 Analyze the conversation and respond with ONLY a JSON object (no other text):
 {"complete": true, "reason": "brief explanation"}
diff --git a/spec/enterprise/controllers/api/v1/accounts/captain/documents_controller_spec.rb b/spec/enterprise/controllers/api/v1/accounts/captain/documents_controller_spec.rb
index 77cb25f49..4d4b10fcb 100644
--- a/spec/enterprise/controllers/api/v1/accounts/captain/documents_controller_spec.rb
+++ b/spec/enterprise/controllers/api/v1/accounts/captain/documents_controller_spec.rb
@@ -51,6 +51,18 @@ RSpec.describe 'Api::V1::Accounts::Captain::Documents', type: :request do
           expect(json_response[:payload].length).to eq(5)
           expect(json_response[:meta]).to eq({ page: 2, total_count: 30 })
         end
+
+        it 'returns the generated FAQ count for each document' do
+          document = create(:captain_document, assistant: assistant, account: account)
+          create_list(:captain_assistant_response, 2,
+                      assistant: assistant, account: account, documentable: document)
+
+          get "/api/v1/accounts/#{account.id}/captain/documents",
+              headers: agent.create_new_auth_token, as: :json
+
+          matching_document = json_response[:payload].find { |item| item[:id] == document.id }
+          expect(matching_document[:responses_count]).to eq(2)
+        end
       end
 
       context 'when filtering by assistant_id' do
@@ -142,6 +154,10 @@ RSpec.describe 'Api::V1::Accounts::Captain::Documents', type: :request do
         expect(json_response[:external_link]).to eq(document.external_link)
       end
 
+      it 'returns the crawled content for the document' do
+        expect(json_response[:content]).to eq(document.content)
+      end
+
       it 'returns sync metadata when the document has been synced' do
         synced_at = 1.hour.ago
         document.update!(sync_status: :synced, last_synced_at: synced_at)
diff --git a/spec/enterprise/lib/captain/conversation_completion_service_spec.rb b/spec/enterprise/lib/captain/conversation_completion_service_spec.rb
index 80b9ab1d8..9cdfc822c 100644
--- a/spec/enterprise/lib/captain/conversation_completion_service_spec.rb
+++ b/spec/enterprise/lib/captain/conversation_completion_service_spec.rb
@@ -68,6 +68,110 @@ RSpec.describe Captain::ConversationCompletionService do
       end
     end
 
+    context 'when building evaluation context' do
+      let(:captain_assistant) { create(:captain_assistant, account: account) }
+      let(:mock_response) do
+        instance_double(
+          RubyLLM::Message,
+          content: { 'complete' => false, 'reason' => 'Human follow-up is still pending' },
+          input_tokens: 100,
+          output_tokens: 20
+        )
+      end
+
+      it 'includes conversation status and speaker labels' do
+        conversation.update!(status: :pending, waiting_since: 2.hours.ago)
+        create(:message, conversation: conversation, inbox: inbox, account: account, message_type: :incoming, content: 'I need help with a refund')
+        create(
+          :message,
+          conversation: conversation,
+          inbox: inbox,
+          account: account,
+          message_type: :outgoing,
+          sender: captain_assistant,
+          content: 'I will transfer this to support for review.'
+        )
+
+        expect(mock_chat).to receive(:ask) do |content|
+          expect(content).to include(
+            'Conversation status: pending',
+            'Conversation transcript:',
+            'Customer: I need help with a refund',
+            'Captain: I will transfer this to support for review.'
+          )
+
+          mock_response
+        end
+
+        result = service.perform
+
+        expect(result[:complete]).to be false
+      end
+
+      it 'includes pending captain handoff evidence in the transcript' do
+        conversation.update!(status: :pending)
+        create(:message, conversation: conversation, inbox: inbox, account: account, message_type: :incoming, content: 'Please cancel my order')
+        create(
+          :message,
+          conversation: conversation,
+          inbox: inbox,
+          account: account,
+          message_type: :outgoing,
+          sender: captain_assistant,
+          content: 'I will transfer this to a specialist and they will follow up here.'
+        )
+
+        expect(mock_chat).to receive(:ask) do |content|
+          expect(content).to include(
+            'Conversation status: pending',
+            'Captain: I will transfer this to a specialist and they will follow up here.'
+          )
+
+          mock_response
+        end
+
+        result = service.perform
+
+        expect(result[:complete]).to be false
+      end
+
+      it 'reuses computed message content while formatting the transcript' do
+        content_for_llm_calls_by_message_id = Hash.new(0)
+        allow_any_instance_of(Message).to receive(:content_for_llm).and_wrap_original do |method, *args| # rubocop:disable RSpec/AnyInstance
+          content_for_llm_calls_by_message_id[method.receiver.id] += 1
+          method.call(*args)
+        end
+
+        incoming_message = create(
+          :message,
+          :with_attachment,
+          conversation: conversation,
+          inbox: inbox,
+          account: account,
+          message_type: :incoming,
+          content: nil
+        )
+        outgoing_message = create(
+          :message,
+          conversation: conversation,
+          inbox: inbox,
+          account: account,
+          message_type: :outgoing,
+          sender: captain_assistant,
+          content: 'What do you need help with?'
+        )
+
+        allow(mock_chat).to receive(:ask).and_return(mock_response)
+
+        service.perform
+
+        expect(content_for_llm_calls_by_message_id).to include(
+          incoming_message.id => 1,
+          outgoing_message.id => 1
+        )
+      end
+    end
+
     context 'when conversation has no messages' do
       it 'returns incomplete with appropriate reason' do
         result = service.perform
diff --git a/spec/enterprise/models/captain/agent_session_spec.rb b/spec/enterprise/models/captain/agent_session_spec.rb
new file mode 100644
index 000000000..b4306a11e
--- /dev/null
+++ b/spec/enterprise/models/captain/agent_session_spec.rb
@@ -0,0 +1,160 @@
+require 'rails_helper'
+
+RSpec.describe Captain::AgentSession, type: :model do
+  let(:account) { create(:account) }
+  let(:assistant) { create(:captain_assistant, account: account) }
+
+  describe 'associations' do
+    it { is_expected.to belong_to(:account) }
+    it { is_expected.to belong_to(:assistant).class_name('Captain::Assistant') }
+    it { is_expected.to belong_to(:user).optional }
+    it { is_expected.to belong_to(:subject) }
+    it { is_expected.to belong_to(:result).optional }
+  end
+
+  describe 'enums' do
+    it { is_expected.to define_enum_for(:session_type).with_values(assistant: 0, copilot: 1).with_prefix(:session) }
+  end
+
+  describe '#subject' do
+    it 'returns the conversation for an assistant session' do
+      conversation = create(:conversation, account: account)
+      session = create(:captain_agent_session, account: account, assistant: assistant, subject: conversation)
+
+      expect(session.subject).to eq(conversation)
+    end
+
+    it 'returns the copilot thread for a copilot session' do
+      user = create(:user, account: account)
+      copilot_thread = create(:captain_copilot_thread, account: account, user: user, assistant: assistant)
+      session = create(:captain_agent_session, :copilot, account: account, assistant: assistant, user: user, subject: copilot_thread)
+
+      expect(session.subject).to eq(copilot_thread)
+    end
+
+    it 'returns nil when the subject record no longer exists' do
+      conversation = create(:conversation, account: account)
+      session = create(:captain_agent_session, account: account, assistant: assistant, subject: conversation)
+      conversation.destroy
+
+      expect(session.reload.subject).to be_nil
+    end
+
+    it 'is not valid when the subject type does not match the session type' do
+      copilot_thread = create(:captain_copilot_thread, account: account, user: create(:user, account: account), assistant: assistant)
+      session = build(:captain_agent_session, account: account, assistant: assistant, subject: copilot_thread)
+
+      expect(session).not_to be_valid
+      expect(session.errors[:subject_type]).to be_present
+    end
+
+    it 'is not valid when the subject belongs to a different account' do
+      foreign_conversation = create(:conversation, account: create(:account))
+      session = build(:captain_agent_session, account: account, assistant: assistant, subject: foreign_conversation)
+
+      expect(session).not_to be_valid
+      expect(session.errors[:subject]).to be_present
+    end
+  end
+
+  describe '#result' do
+    it 'returns the message for an assistant session' do
+      conversation = create(:conversation, account: account)
+      message = create(:message, account: account, conversation: conversation)
+      session = create(:captain_agent_session, account: account, assistant: assistant, subject: conversation, result: message)
+
+      expect(session.result).to eq(message)
+    end
+
+    it 'returns the copilot message for a copilot session' do
+      user = create(:user, account: account)
+      copilot_thread = create(:captain_copilot_thread, account: account, user: user, assistant: assistant)
+      copilot_message = create(:captain_copilot_message, account: account, copilot_thread: copilot_thread)
+      session = create(:captain_agent_session, :copilot, account: account, assistant: assistant, user: user,
+                                                         subject: copilot_thread, result: copilot_message)
+
+      expect(session.result).to eq(copilot_message)
+    end
+
+    it 'returns nil when result_id is nil' do
+      session = create(:captain_agent_session, account: account, assistant: assistant)
+
+      expect(session.result).to be_nil
+    end
+
+    it 'is not valid when the result belongs to a different account' do
+      conversation = create(:conversation, account: account)
+      foreign_message = create(:message, account: create(:account))
+      session = build(:captain_agent_session, account: account, assistant: assistant, subject: conversation, result: foreign_message)
+
+      expect(session).not_to be_valid
+      expect(session.errors[:result]).to be_present
+    end
+
+    it 'is not valid when result_id/result_type are set directly for a different account' do
+      conversation = create(:conversation, account: account)
+      foreign_message = create(:message, account: create(:account))
+      session = build(:captain_agent_session, account: account, assistant: assistant, subject: conversation,
+                                              result_id: foreign_message.id, result_type: 'Message')
+
+      expect(session).not_to be_valid
+      expect(session.errors[:result]).to be_present
+    end
+
+    it 'is not valid when result_id/result_type are set directly for a stale id' do
+      conversation = create(:conversation, account: account)
+      session = build(:captain_agent_session, account: account, assistant: assistant, subject: conversation,
+                                              result_id: 0, result_type: 'Message')
+
+      expect(session).not_to be_valid
+      expect(session.errors[:result]).to be_present
+    end
+  end
+
+  describe 'account' do
+    it 'is derived from the assistant when created via the assistant association' do
+      conversation = create(:conversation, account: account)
+      session = assistant.agent_sessions.create!(subject: conversation, session_type: :assistant)
+
+      expect(session.account).to eq(account)
+    end
+
+    it 'overrides a mismatched explicit account with the assistant account' do
+      conversation = create(:conversation, account: account)
+      session = build(:captain_agent_session, account: create(:account), assistant: assistant, subject: conversation)
+
+      expect(session).to be_valid
+      expect(session.account).to eq(account)
+    end
+  end
+
+  describe 'defaults' do
+    it 'defaults faq_ids, document_ids, scenario_ids and run_context' do
+      session = create(:captain_agent_session, account: account, assistant: assistant)
+
+      expect(session.faq_ids).to eq([])
+      expect(session.document_ids).to eq([])
+      expect(session.scenario_ids).to eq([])
+      expect(session.run_context).to eq({})
+    end
+  end
+
+  describe 'factory' do
+    it 'builds a valid assistant session' do
+      session = create(:captain_agent_session, account: account, assistant: assistant)
+
+      expect(session).to be_valid
+      expect(session).to be_session_assistant
+      expect(session.subject).to be_a(Conversation)
+    end
+
+    it 'builds a valid copilot session' do
+      session = create(:captain_agent_session, :copilot, account: account, assistant: assistant)
+
+      expect(session).to be_valid
+      expect(session).to be_session_copilot
+      expect(session.subject).to be_a(CopilotThread)
+      expect(session.user).to be_present
+    end
+  end
+end
diff --git a/spec/factories/captain/agent_session.rb b/spec/factories/captain/agent_session.rb
new file mode 100644
index 000000000..a7b369b7d
--- /dev/null
+++ b/spec/factories/captain/agent_session.rb
@@ -0,0 +1,14 @@
+FactoryBot.define do
+  factory :captain_agent_session, class: 'Captain::AgentSession' do
+    account
+    association :assistant, factory: :captain_assistant
+    session_type { :assistant }
+    subject { create(:conversation, account: account) }
+
+    trait :copilot do
+      session_type { :copilot }
+      user
+      subject { create(:captain_copilot_thread, account: account, user: user) }
+    end
+  end
+end
diff --git a/spec/services/whatsapp/webhook_teardown_service_spec.rb b/spec/services/whatsapp/webhook_teardown_service_spec.rb
index be94f3c44..a5bdeef0b 100644
--- a/spec/services/whatsapp/webhook_teardown_service_spec.rb
+++ b/spec/services/whatsapp/webhook_teardown_service_spec.rb
@@ -51,18 +51,41 @@ RSpec.describe Whatsapp::WebhookTeardownService do
       end
     end
 
-    context 'when channel is whatsapp_cloud but not embedded_signup' do
+    context 'when channel is whatsapp_cloud with manual setup' do
       before do
+        allow(channel).to receive(:setup_webhooks).and_return(true)
+
         channel.update!(
           provider: 'whatsapp_cloud',
-          provider_config: { 'source' => 'manual' }
+          provider_config: {
+            'source' => 'manual',
+            'phone_number_id' => 'manual_phone_id',
+            'business_account_id' => 'manual_waba_id',
+            'api_key' => 'manual_api_key'
+          }
         )
       end
 
-      it 'does not attempt to unsubscribe webhook' do
-        expect(Whatsapp::FacebookApiClient).not_to receive(:new)
+      it 'clears the phone number callback override' do
+        api_client = instance_double(Whatsapp::FacebookApiClient)
+        allow(Whatsapp::FacebookApiClient).to receive(:new).with('manual_api_key').and_return(api_client)
+        allow(api_client).to receive(:clear_phone_number_callback_override).with('manual_phone_id')
 
         service.perform
+
+        expect(api_client).to have_received(:clear_phone_number_callback_override).with('manual_phone_id')
+      end
+
+      # The manual token belongs to the customer's own Meta app, so its WABA subscription is not ours to remove.
+      it 'does not unsubscribe the app from the WABA' do
+        api_client = instance_double(Whatsapp::FacebookApiClient)
+        allow(Whatsapp::FacebookApiClient).to receive(:new).and_return(api_client)
+        allow(api_client).to receive(:clear_phone_number_callback_override)
+        allow(api_client).to receive(:unsubscribe_app_from_waba)
+
+        service.perform
+
+        expect(api_client).not_to have_received(:unsubscribe_app_from_waba)
       end
     end