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

apps/dashboard/src/lib/features/ai-assistant/api/ai-assistant.svelte.ts

@@ -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;

apps/dashboard/src/lib/features/ai-assistant/chat-input.svelte

@@ -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}

apps/dashboard/src/lib/features/ai-assistant/message-bubble.svelte

@@ -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}

apps/dashboard/src/lib/features/ai-assistant/plan-view.svelte

@@ -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">

apps/dashboard/src/lib/utils/translations/da.json

@@ -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",

apps/dashboard/src/lib/utils/translations/de.json

@@ -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",

apps/dashboard/src/lib/utils/translations/en.json

@@ -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",

apps/dashboard/src/lib/utils/translations/es.json

@@ -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",

apps/dashboard/src/lib/utils/translations/fr.json

@@ -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",

apps/dashboard/src/lib/utils/translations/hi.json

@@ -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",

apps/dashboard/src/lib/utils/translations/pl.json

@@ -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",

apps/dashboard/src/lib/utils/translations/pt.json

@@ -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",

apps/dashboard/src/lib/utils/translations/ru.json

@@ -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",

apps/dashboard/src/lib/utils/translations/vi.json

@@ -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",