feat(ai-assistant): odt support, document-to-lesson attach, upload UX fixes

- Add .odt (application/vnd.oasis.opendocument.text) as a supported upload format; extract text via JSZip + content.xml parsing - Add attach_document_to_lesson agent tool so the AI can attach an uploaded document to a lesson as a downloadable material - Instruct the agent to create a "Course Materials" lesson (first lesson of the first section) and attach the uploaded document to it on implementation - Suppress hallucinated references: uploaded documents do not count as fetched URLs — omit the References section when no fetch_documentation_url calls were made - Surface specific upload error snackbars (file_too_large, unsupported_file_type) instead of silently logging; fix generic fallback message - Allow typing in the chat textarea while a document is uploading; only block Enter/send, not the whole input - Fix retry endpoint to return the current run instead of erroring when the run is already active (queued/running/waiting_for_input/paused) - Connect @cio/core Redis singleton in the jobs bootstrap so course-generation workers no longer fail with "The client is closed" - Expose documentAssets (assetId + fileName) alongside documentText in AgentContext and pass it through both the chat route and course runner
2026-06-29 12:29:47 +01:00
parent 773fc873c2
commit 65420320e7
24 changed files with 235 additions and 27 deletions
@@ -69,6 +69,7 @@ import {
  collectDocumentIds,
  getActiveCourseTemplateId,
  getLatestImplementationPlan,
+  loadDocumentsMeta,
  loadDocumentsText,
  verifyExerciseBelongsToCourse,
  verifyLessonBelongsToCourse
@@ -410,6 +411,7 @@ const agentCoreRouter = new Hono()
        .select({
          title: schema.course.title,
          description: schema.course.description,
+          metadata: schema.course.metadata,
          organizationId: schema.group.organizationId
        })
        .from(schema.course)
@@ -449,7 +451,10 @@ const agentCoreRouter = new Hono()
      }

      const documentIds = collectDocumentIds(messages, context?.documentId);
-      const documentText = documentIds.length > 0 ? await loadDocumentsText(documentIds, user.id) : undefined;
+      const [documentText, documentAssets] = await Promise.all([
+        documentIds.length > 0 ? loadDocumentsText(documentIds, user.id) : Promise.resolve(undefined),
+        documentIds.length > 0 ? loadDocumentsMeta(documentIds) : Promise.resolve([])
+      ]);

      const existingSections = await listCourseSections(courseId);

@@ -496,7 +501,9 @@ const agentCoreRouter = new Hono()
        exerciseTitle,
        documentId: context?.documentId,
        documentText,
-        existingSectionCount: existingSections.length
+        documentAssets,
+        existingSectionCount: existingSections.length,
+        isContentGroupingEnabled: courseRow.metadata?.isContentGroupingEnabled ?? true
      };

      trackAgentEvent(AgentEvent.CHAT_STARTED, {
@@ -531,7 +538,9 @@ const agentCoreRouter = new Hono()
      const agentTools =
        role === AgentRole.STUDENT
          ? buildStudentAgentTools(orgId, user.id, courseId, studentPolicy!.settings)
-          : filterToolsForChatMode(buildAgentTools(orgId, user.id, courseId, messages, { isOrgOnPaidPlan: isOrgPaid }));
+          : filterToolsForChatMode(
+              buildAgentTools(orgId, user.id, courseId, messages, { isOrgOnPaidPlan: isOrgPaid, documentAssets })
+            );

      const contextManaged = await buildModelContextMessages({
        conversationId,
@@ -331,6 +331,10 @@ export async function resumeAgentRunState(runId: string, userId: string, orgId:
 export async function retryAgentRunState(runId: string, userId: string, orgId: string): Promise<AgentRunDetail> {
  const run = await getOwnedAgentRun(runId, userId, orgId);

+  if (ACTIVE_RUN_STATUSES.has(run.status)) {
+    return buildAgentRunDetail(run);
+  }
+
  if (run.status !== 'failed') {
    throw new AppError('Only failed agent runs can be retried', 'AGENT_RUN_NOT_RETRYABLE', 409);
  }
@@ -1,4 +1,6 @@
 import { BaseApiWithErrors, classroomio, apiClient, getRequestBaseUrl } from '$lib/utils/services/api';
+import { snackbar } from '$features/ui/snackbar/store';
+import { t } from '$lib/utils/functions/translations';
 import type {
  AgentConversation,
  AgentConversationCreateData,
@@ -158,7 +160,25 @@ class AiAssistantApi extends BaseApiWithErrors {
      }
    } catch (error) {
      console.error('Error uploading document:', error);
-      this.error = 'Failed to upload document';
+
+      let errorCode: string | null = null;
+
+      if (error instanceof Error) {
+        try {
+          const body = JSON.parse(error.message) as { error?: string };
+          errorCode = body.error ?? null;
+        } catch {
+          // message was not JSON
+        }
+      }
+
+      if (errorCode === 'file_too_large') {
+        snackbar.error(t.get('ai_assistant.upload_error_file_too_large'));
+      } else if (errorCode === 'unsupported_file_type') {
+        snackbar.error(t.get('ai_assistant.upload_error_unsupported_type'));
+      } else {
+        snackbar.error(t.get('ai_assistant.upload_error_generic'));
+      }
    }

    return null;
@@ -175,7 +175,7 @@
 <input
  bind:this={fileInputEl}
  type="file"
-  accept=".pdf,.docx,.pptx,application/pdf,application/vnd.openxmlformats-officedocument.wordprocessingml.document,application/vnd.openxmlformats-officedocument.presentationml.presentation"
+  accept=".pdf,.docx,.pptx,.odt,application/pdf,application/vnd.openxmlformats-officedocument.wordprocessingml.document,application/vnd.openxmlformats-officedocument.presentationml.presentation,application/vnd.oasis.opendocument.text"
  class="hidden"
  onchange={handleFileChange}
 />
@@ -255,9 +255,9 @@
          bind:ref={chatTextareaRef}
          bind:value={inputValue}
          {mentionItems}
-          onSubmit={onSend}
+          onSubmit={isUploading ? undefined : onSend}
          placeholder={$t('ai_assistant.input_placeholder')}
-          disabled={isStreaming || isUploading}
+          disabled={isStreaming}
          typeLabel={getTypeLabel}
          emptyMessage={t.get('ai_assistant.mention_no_results')}
          rows={2}
@@ -151,7 +151,7 @@
            ? 'bg-white/15 text-white/90'
            : 'ui:bg-background/70 ui:text-muted-foreground'}"
        >
-          <FileTextIcon size={12} class="shrink-0" />
+          <FileTextIcon size={12} class="custom shrink-0" />
          <span class="min-w-0 truncate">{messageAttachment.name}</span>
        </div>
      {/if}
@@ -5,6 +5,7 @@
  import FileQuestionIcon from '@lucide/svelte/icons/file-question';
  import PencilIcon from '@lucide/svelte/icons/pencil';
  import ArrowUpIcon from '@lucide/svelte/icons/arrow-up';
+  import LoaderIcon from '@lucide/svelte/icons/loader';
  import { Button } from '@cio/ui/base/button';
  import { Textarea } from '@cio/ui/base/textarea';
  import { SvelteSet } from 'svelte/reactivity';
@@ -53,6 +54,12 @@
    isExpanded = !defaultCollapsed;
  });

+  let isImplementing = $state(false);
+
+  $effect(() => {
+    if (isBusy) isImplementing = false;
+  });
+
  let changeRequest = $state('');
  const canSendChange = $derived(!isBusy && changeRequest.trim().length > 0);

@@ -301,7 +308,18 @@
      {/if}

      <div class="flex flex-col gap-2">
-        <Button size="sm" onclick={() => onImplement(editablePlan)} class="w-full">
+        <Button
+          size="sm"
+          disabled={isImplementing || isBusy}
+          onclick={() => {
+            isImplementing = true;
+            onImplement(editablePlan);
+          }}
+          class="w-full"
+        >
+          {#if isImplementing || isBusy}
+            <LoaderIcon size={14} class="animate-spin" />
+          {/if}
          {$t('ai_assistant.plan_implement')}
        </Button>
        <div class="flex items-end gap-2">
@@ -4316,7 +4316,10 @@
    "ask_ai": "Spørg AI",
    "content_input_placeholder": "Spørg om dette indhold...",
    "ask_ai_expand_aria": "Åbn Spørg AI-input",
-    "ask_ai_input_aria": "Spørg AI om dette indhold"
+    "ask_ai_input_aria": "Spørg AI om dette indhold",
+    "upload_error_file_too_large": "Filen er for stor. Maksimal størrelse er 5 MB.",
+    "upload_error_unsupported_type": "Filtype understøttes ikke. Upload venligst en PDF-, DOCX-, PPTX- eller ODT-fil.",
+    "upload_error_generic": "Kunne ikke uploade dokument. Prøv venligst igen."
  },
  "widgets": {
    "heading": "Widgets",
@@ -4316,7 +4316,10 @@
    "ask_ai": "Fragen Sie die KI",
    "content_input_placeholder": "Fragen Sie nach diesem Inhalt…",
    "ask_ai_expand_aria": "Öffnen Sie „Ask AI Input“.",
-    "ask_ai_input_aria": "Fragen Sie AI nach diesem Inhalt"
+    "ask_ai_input_aria": "Fragen Sie AI nach diesem Inhalt",
+    "upload_error_file_too_large": "Die Datei ist zu groß. Die maximale Größe beträgt 5 MB.",
+    "upload_error_unsupported_type": "Dateityp wird nicht unterstützt. Bitte laden Sie eine PDF-, DOCX-, PPTX- oder ODT-Datei hoch.",
+    "upload_error_generic": "Das Hochladen des Dokuments ist fehlgeschlagen. Bitte versuchen Sie es erneut."
  },
  "widgets": {
    "heading": "Widgets",
@@ -4613,7 +4613,10 @@
    "ask_ai_expand_aria": "Open Ask AI input",
    "ask_ai_input_aria": "Ask AI about this content",
    "quote_lesson_note": "Quote in assistant",
-    "attach_document": "Attach a document (PDF, DOCX, PPTX)",
+    "attach_document": "Attach a document (PDF, DOCX, PPTX, ODT)",
+    "upload_error_file_too_large": "File is too large. Maximum size is 5 MB.",
+    "upload_error_unsupported_type": "File type not supported. Please upload a PDF, DOCX, PPTX, or ODT file.",
+    "upload_error_generic": "Failed to upload document. Please try again.",
    "upgrade_to_upload": "Upgrade to upload documents",
    "tokens_exhausted": "Monthly AI token limit reached.",
    "tokens_exhausted_buy_more": "Buy more",
@@ -4316,7 +4316,10 @@
    "ask_ai": "Pregúntale a la IA",
    "content_input_placeholder": "Pregunta por este contenido...",
    "ask_ai_expand_aria": "Abrir Preguntar entrada a AI",
-    "ask_ai_input_aria": "Pregúntale a AI sobre este contenido"
+    "ask_ai_input_aria": "Pregúntale a AI sobre este contenido",
+    "upload_error_file_too_large": "El archivo es demasiado grande. El tamaño máximo es 5 MB.",
+    "upload_error_unsupported_type": "Tipo de archivo no compatible. Cargue un archivo PDF, DOCX, PPTX u ODT.",
+    "upload_error_generic": "No se pudo cargar el documento. Por favor inténtalo de nuevo."
  },
  "widgets": {
    "heading": "widgets",
@@ -4316,7 +4316,10 @@
    "ask_ai": "Demandez à l'IA",
    "content_input_placeholder": "Renseignez-vous sur ce contenu…",
    "ask_ai_expand_aria": "Ouvrir la saisie de Ask AI",
-    "ask_ai_input_aria": "Interrogez AI à propos de ce contenu"
+    "ask_ai_input_aria": "Interrogez AI à propos de ce contenu",
+    "upload_error_file_too_large": "Le fichier est trop volumineux. La taille maximale est de 5 Mo.",
+    "upload_error_unsupported_type": "Type de fichier non pris en charge. Veuillez télécharger un fichier PDF, DOCX, PPTX ou ODT.",
+    "upload_error_generic": "Échec du téléchargement du document. Veuillez réessayer."
  },
  "widgets": {
    "heading": "Widgets",
@@ -4316,7 +4316,10 @@
    "ask_ai": "एआई से पूछें",
    "content_input_placeholder": "इस सामग्री के बारे में पूछें...",
    "ask_ai_expand_aria": "एआई इनपुट पूछें खोलें",
-    "ask_ai_input_aria": "इस सामग्री के बारे में AI से पूछें"
+    "ask_ai_input_aria": "इस सामग्री के बारे में AI से पूछें",
+    "upload_error_file_too_large": "फ़ाइल बहुत बड़ी है। अधिकतम आकार 5 एमबी है.",
+    "upload_error_unsupported_type": "फ़ाइल प्रकार समर्थित नहीं है. कृपया एक PDF, DOCX, PPTX, या ODT फ़ाइल अपलोड करें।",
+    "upload_error_generic": "दस्तावेज़ अपलोड करने में विफल. कृपया पुन: प्रयास करें।"
  },
  "widgets": {
    "heading": "विजेट्स",
@@ -4316,7 +4316,10 @@
    "ask_ai": "Zapytaj AI",
    "content_input_placeholder": "Zapytaj o tę treść…",
    "ask_ai_expand_aria": "Otwórz wejście Zapytaj AI",
-    "ask_ai_input_aria": "Zapytaj AI o tę treść"
+    "ask_ai_input_aria": "Zapytaj AI o tę treść",
+    "upload_error_file_too_large": "Plik jest za duży. Maksymalny rozmiar to 5 MB.",
+    "upload_error_unsupported_type": "Typ pliku nie jest obsługiwany. Prześlij plik PDF, DOCX, PPTX lub ODT.",
+    "upload_error_generic": "Nie udało się przesłać dokumentu. Spróbuj ponownie."
  },
  "widgets": {
    "heading": "Widżety",
@@ -4316,7 +4316,10 @@
    "ask_ai": "Pergunte à IA",
    "content_input_placeholder": "Pergunte sobre este conteúdo…",
    "ask_ai_expand_aria": "Abra a entrada Ask AI",
-    "ask_ai_input_aria": "Pergunte à IA sobre este conteúdo"
+    "ask_ai_input_aria": "Pergunte à IA sobre este conteúdo",
+    "upload_error_file_too_large": "O arquivo é muito grande. O tamanho máximo é 5 MB.",
+    "upload_error_unsupported_type": "Tipo de arquivo não suportado. Faça upload de um arquivo PDF, DOCX, PPTX ou ODT.",
+    "upload_error_generic": "Falha ao carregar o documento. Por favor, tente novamente."
  },
  "widgets": {
    "heading": "Widgets",
@@ -4316,7 +4316,10 @@
    "ask_ai": "Спросите ИИ",
    "content_input_placeholder": "Спросите об этом контенте…",
    "ask_ai_expand_aria": "Открыть вход Ask AI",
-    "ask_ai_input_aria": "Спросите ИИ об этом контенте"
+    "ask_ai_input_aria": "Спросите ИИ об этом контенте",
+    "upload_error_file_too_large": "Файл слишком большой. Максимальный размер — 5 МБ.",
+    "upload_error_unsupported_type": "Тип файла не поддерживается. Загрузите файл PDF, DOCX, PPTX или ODT.",
+    "upload_error_generic": "Не удалось загрузить документ. Пожалуйста, попробуйте еще раз."
  },
  "widgets": {
    "heading": "Виджеты",
@@ -4316,7 +4316,10 @@
    "ask_ai": "Hỏi AI",
    "content_input_placeholder": "Hỏi về nội dung này…",
    "ask_ai_expand_aria": "Mở đầu vào Hỏi AI",
-    "ask_ai_input_aria": "Hỏi AI về nội dung này"
+    "ask_ai_input_aria": "Hỏi AI về nội dung này",
+    "upload_error_file_too_large": "Tệp quá lớn. Kích thước tối đa là 5 MB.",
+    "upload_error_unsupported_type": "Loại tệp không được hỗ trợ. Vui lòng tải lên tệp PDF, DOCX, PPTX hoặc ODT.",
+    "upload_error_generic": "Không thể tải tài liệu lên. Vui lòng thử lại."
  },
  "widgets": {
    "heading": "Widget",
@@ -3,6 +3,7 @@ import 'dotenv/config';
 import { env } from './config/env';
 import { warnIfFfmpegMissing } from './utils/ffmpeg';
 import { log } from './utils/logger';
+import { connectRedis } from '@cio/core/utils/redis/redis';

 void warnIfFfmpegMissing();

@@ -10,6 +11,8 @@ if (!env.REDIS_URL) {
  throw new Error('REDIS_URL is required to start a worker process.');
 }

+void connectRedis();
+
 log.info('worker-bootstrap', {
  nodeEnv: env.NODE_ENV,
  pid: process.pid,
@@ -279,6 +279,8 @@ If this conversation contains any successful \`fetch_documentation_url\` tool re

 When any \`fetch_documentation_url\` results exist in this conversation, **every** lesson you create or update via \`update_lesson_content\` MUST end with a References section so the teacher can verify your sourcing. Skip the References section ONLY when zero docs have been fetched in the entire conversation.

+**Uploaded documents do NOT count as fetched documentation for the purposes of References.** If the only source material is an uploaded document (no \`fetch_documentation_url\` calls were made), omit the References section entirely — do not fabricate URLs or cite the document by a made-up link.
+
 Format the section as the last block of the lesson HTML, in this exact shape:

 \`\`\`html
@@ -431,11 +433,30 @@ export function buildTeacherContextMessage(
    contextLines.push(exerciseInfo);
  }
  if (context.documentText) {
+    const docAssets = context.documentAssets ?? [];
+    const assetLines = docAssets
+      .filter((d) => d.assetId)
+      .map((d) => `- documentId: ${d.documentId}, fileName: ${d.fileName}`)
+      .join('\n');
+
+    const courseMaterialsInstruction =
+      assetLines.length > 0
+        ? `\n\nWhen implementing a course plan, create a lesson titled **"Course Materials"** as the **first lesson of the first section**. Give it no text content. Then immediately call \`attach_document_to_lesson\` for each document listed below to attach the original file to that lesson:\n${assetLines}`
+        : '';
+
    contextLines.push(
-      `The teacher has uploaded a document. Use this content as the source material for course planning and content generation:\n\n<document>\n${context.documentText}\n</document>`
+      `The teacher has uploaded a document. Use this content as the source material for course planning and content generation:${courseMaterialsInstruction}\n\n<document>\n${context.documentText}\n</document>`
    );
  }
-  if (context.existingSectionCount && context.existingSectionCount > 0) {
+  if (context.isContentGroupingEnabled === false) {
+    contextLines.push(
+      `**Content grouping is DISABLED for this course.** Lessons and exercises are displayed as a flat ordered list — sections are invisible to students and teachers. Follow these rules strictly:\n` +
+        `- Do NOT plan or create multiple sections. Use exactly ONE section as a technical container for all content.\n` +
+        `- In \`generate_course_plan\`, output a single section whose title matches the course title. Place all lessons and exercises as items inside that one section, ordered sequentially (order 0, 1, 2, …).\n` +
+        `- When implementing a plan, create that one section first, then add every lesson and exercise into it with strictly ascending \`order\` values (0, 1, 2, …). The order field is the only thing that controls the visible sequence.\n` +
+        `- Never call \`create_section\` more than once for this course.`
+    );
+  } else if (context.existingSectionCount && context.existingSectionCount > 0) {
    contextLines.push(
      `This course already has ${context.existingSectionCount} sections. When creating new sections, set their order values starting after the existing sections.`
    );
@@ -43,7 +43,11 @@ export interface AgentContext {
  exerciseTitle?: string;
  documentId?: string;
  documentText?: string;
+  /** Metadata for documents attached to this conversation — used to attach originals to lessons. */
+  documentAssets?: { documentId: string; assetId: string | null; fileName: string }[];
  existingSectionCount?: number;
+  /** When false, content grouping is disabled: lessons/exercises are displayed as a flat ordered list and sections are hidden from students. */
+  isContentGroupingEnabled?: boolean;
 }

 // ─── Course Plan (generated by the agent in Plan Mode) ───────────────────────
@@ -215,11 +219,12 @@ export const MAX_STEPS_PER_ROUND = 15;
 export const SUPPORTED_DOCUMENT_TYPES = [
  'application/pdf',
  'application/vnd.openxmlformats-officedocument.wordprocessingml.document',
-  'application/vnd.openxmlformats-officedocument.presentationml.presentation'
+  'application/vnd.openxmlformats-officedocument.presentationml.presentation',
+  'application/vnd.oasis.opendocument.text'
 ] as const;

 /** Supported file extensions for document upload */
-export const SUPPORTED_DOCUMENT_EXTENSIONS = ['.pdf', '.docx', '.pptx'] as const;
+export const SUPPORTED_DOCUMENT_EXTENSIONS = ['.pdf', '.docx', '.pptx', '.odt'] as const;

 /** Token cost estimation heuristics (tokens per item) */
 export const TOKEN_COST_ESTIMATES = {
@@ -42,6 +42,10 @@ export const createLessonParam = z.object({
  title: z.string().min(1),
  order: z.number().int().min(0)
 });
+export const attachDocumentToLessonParam = z.object({
+  lessonId: z.string().describe('ID of the lesson to attach the document to'),
+  documentId: z.string().describe('documentId of the uploaded document (from the conversation context)')
+});
 export const updateLessonParam = z
  .object({
    lessonId: z.string(),
@@ -1,7 +1,12 @@
 import { AppError } from '@cio/utils/errors';
 import { getDocumentText } from './document';
 import { redis } from '../../utils/redis/redis';
-import { getCourseSectionBinding, getExerciseCourseBinding, getLessonCourseBinding } from '@cio/db/queries/agent';
+import {
+  getCourseSectionBinding,
+  getExerciseCourseBinding,
+  getLessonCourseBinding,
+  getChatDocumentsByIds
+} from '@cio/db/queries/agent';
 import { z } from 'zod';
 import { CoursePlanFieldsSchema, type CourseTemplateId } from '@cio/ai-assistant';

@@ -113,6 +118,16 @@ export function collectDocumentIds(messages: unknown[], currentDocumentId?: stri
  return Array.from(ids);
 }

+export async function loadDocumentsMeta(
+  documentIds: string[]
+): Promise<{ documentId: string; assetId: string | null; fileName: string }[]> {
+  if (documentIds.length === 0) return [];
+
+  const records = await getChatDocumentsByIds(documentIds);
+
+  return records.map((r) => ({ documentId: r.id, assetId: r.assetId, fileName: r.fileName }));
+}
+
 export async function loadDocumentsText(documentIds: string[], userId: string): Promise<string | undefined> {
  const loaded = await Promise.all(
    documentIds.map(async (id) => {
@@ -44,6 +44,7 @@ import {
  coursePlanParam,
  createExerciseParam,
  createExerciseSectionParam,
+  attachDocumentToLessonParam,
  createLessonParam,
  createSectionParam,
  emptyParam,
@@ -61,6 +62,7 @@ import {
  updateQuestionsParam,
  updateSectionParam
 } from './agent-tool-schemas';
+import { attachAssetService } from '../assets/assets';
 import { fetchDocumentationUrl } from './fetch-url';

 const DURABLE_AGENT_TOOL_NAMES = new Set([
@@ -69,6 +71,7 @@ const DURABLE_AGENT_TOOL_NAMES = new Set([
  'create_lesson',
  'update_lesson',
  'update_lesson_content',
+  'attach_document_to_lesson',
  'create_exercise',
  'update_exercise',
  'update_exercise_section',
@@ -89,6 +92,8 @@ export interface BuildAgentToolsOptions {
   * premium-only question types.
   */
  isOrgOnPaidPlan?: boolean;
+  /** Documents uploaded in this conversation — used by attach_document_to_lesson. */
+  documentAssets?: { documentId: string; assetId: string | null; fileName: string }[];
 }

 function summarizeAgentDebugValue(value: unknown, depth = 0): unknown {
@@ -451,6 +456,7 @@ export function buildAgentTools(
  options: BuildAgentToolsOptions = {}
 ) {
  const isOrgOnPaidPlan = options.isOrgOnPaidPlan ?? true;
+  const documentAssets = options.documentAssets ?? [];

  const executeAgentTool = <TArgs, TResult>(
    toolName: string,
@@ -611,6 +617,44 @@ export function buildAgentTools(
      }
    }),

+    attach_document_to_lesson: tool({
+      description:
+        'Attach an uploaded document from this conversation to a lesson as a downloadable material. Use this to create the Course Materials lesson — create the lesson first (with no content), then call this tool.',
+      inputSchema: attachDocumentToLessonParam,
+      execute: async (args) => {
+        return executeAgentTool('attach_document_to_lesson', { orgId, userId, courseId, args }, async () => {
+          await verifyLessonBelongsToCourse(args.lessonId, courseId);
+
+          const docAsset = documentAssets.find((d) => d.documentId === args.documentId);
+
+          if (!docAsset) {
+            throw new AppError(
+              `Document "${args.documentId}" not found in this conversation`,
+              'DOCUMENT_NOT_FOUND',
+              404
+            );
+          }
+
+          if (!docAsset.assetId) {
+            throw new AppError(
+              `Document "${args.documentId}" has no associated asset and cannot be attached`,
+              'DOCUMENT_NO_ASSET',
+              422
+            );
+          }
+
+          await attachAssetService(orgId, docAsset.assetId, userId, {
+            targetType: 'lesson',
+            targetId: args.lessonId,
+            slotType: 'lesson_document',
+            position: 0
+          });
+
+          return { lessonId: args.lessonId, fileName: docAsset.fileName, attached: true };
+        });
+      }
+    }),
+
    create_exercise: tool({
      description: 'Create a new exercise with questions and answer options in this course.',
      inputSchema: createExerciseParam,
@@ -20,6 +20,7 @@ import {
  collectDocumentIds,
  getActiveCourseTemplateId,
  getLatestImplementationPlan,
+  loadDocumentsMeta,
  loadDocumentsText
 } from './chat-context';
 import { buildAgentTools } from './chat-tools';
@@ -145,7 +146,10 @@ export async function runAgentCourseGenerationJob(input: RunAgentCourseGeneratio
      : null;
    const visibleMessages = (conversation?.messages ?? []) as Array<Record<string, unknown>>;
    const documentIds = collectDocumentIds(visibleMessages);
-    const documentText = documentIds.length > 0 ? await loadDocumentsText(documentIds, initialRun.userId) : undefined;
+    const [documentText, documentAssets] = await Promise.all([
+      documentIds.length > 0 ? loadDocumentsText(documentIds, initialRun.userId) : Promise.resolve(undefined),
+      documentIds.length > 0 ? loadDocumentsMeta(documentIds) : Promise.resolve([])
+    ]);
    const existingSections = await listCourseSections(initialRun.courseId);
    const executionCursor = initialRun.executionCursor ?? {};
    const modelId = getRunModelId(executionCursor);
@@ -166,6 +170,7 @@ export async function runAgentCourseGenerationJob(input: RunAgentCourseGeneratio
      role: AgentRole.TEACHER,
      locale: 'en',
      documentText,
+      documentAssets,
      existingSectionCount: existingSections.length
    };
    const approvedPlan = initialRun.approvedPlan ?? getLatestImplementationPlan(visibleMessages);
@@ -208,7 +213,8 @@ export async function runAgentCourseGenerationJob(input: RunAgentCourseGeneratio
    const isOrgPaid = await isOrgOnPaidPlan(initialRun.orgId);
    const agentTools = buildAgentTools(initialRun.orgId, initialRun.userId, initialRun.courseId, visibleMessages, {
      runId: initialRun.id,
-      isOrgOnPaidPlan: isOrgPaid
+      isOrgOnPaidPlan: isOrgPaid,
+      documentAssets
    });

    for (let roundIndex = 0; roundIndex < MAX_WORKER_ROUNDS; roundIndex += 1) {
@@ -18,7 +18,7 @@ import { createAssetFromUploadService } from '../assets/assets';

 /**
 * Parse an uploaded document, store extracted text in Redis (hot cache) and Postgres
- * (durable, scoped to a conversation). Supports PDF, DOCX, and PPTX files.
+ * (durable, scoped to a conversation). Supports PDF, DOCX, PPTX, and ODT files.
 */
 export async function parseAndStoreDocument(
  file: File,
@@ -56,6 +56,9 @@ export async function parseAndStoreDocument(
    case 'application/vnd.openxmlformats-officedocument.presentationml.presentation':
      ({ text: extractedText, pageCount } = await extractPptxText(buffer));
      break;
+    case 'application/vnd.oasis.opendocument.text':
+      extractedText = await extractOdtText(buffer);
+      break;
    default:
      throw new AppError('Unsupported file type', 'UNSUPPORTED_FILE_TYPE', 415);
  }
@@ -197,6 +200,32 @@ async function extractDocxText(buffer: Buffer): Promise<string> {
  return result.value;
 }

+async function extractOdtText(buffer: Buffer): Promise<string> {
+  try {
+    const JSZip = (await import('jszip')).default;
+    const zip = await JSZip.loadAsync(buffer);
+
+    const contentFile = zip.files['content.xml'];
+
+    if (!contentFile) {
+      throw new Error('content.xml not found in ODT archive');
+    }
+
+    const xml = await contentFile.async('text');
+    const text = xml
+      .replace(/<text:line-break[^>]*\/?>/g, '\n')
+      .replace(/<\/text:p>/g, '\n')
+      .replace(/<\/text:h>/g, '\n')
+      .replace(/<[^>]+>/g, '')
+      .replace(/\n{3,}/g, '\n\n')
+      .trim();
+
+    return text;
+  } catch {
+    throw new AppError('Failed to parse ODT file', 'ODT_PARSE_ERROR', 422);
+  }
+}
+
 async function extractPptxText(buffer: Buffer): Promise<{ text: string; pageCount: number }> {
  // pptx-parser may not be available yet — use a simpler approach
  // For now, try to use officegen or a basic XML extraction