@studious-lms/server 1.14.0 → 1.16.0

package/dist/pipelines/aiLabChat.d.ts

@@ -57,6 +57,12 @@ type RecentLabChatMessage = {
             displayName: string | null;
         } | null;
     } | null;
+    attachments: {
+        id: string;
+        name: string;
+        type: string;
+        path: string;
+    }[];
 };
 /**
  * `messages` must be ordered newest-first.
@@ -95,7 +101,7 @@ export declare const generateAndSendLabIntroduction: (labChatId: string, convers
  * conversation history is reloaded from the DB anchored on the AI
  * placeholder.
  */
-export declare const generateAndSendLabResponse: (labChatId: string, _teacherMessage: string, emitOptions: {
+export declare const generateAndSendLabResponse: (labChatId: string, teacherMessage: string, emitOptions: {
     classId: string;
     aiMessageId: string;
 }) => Promise<void>;

package/dist/pipelines/aiLabChat.d.ts.map

@@ -1 +1 @@
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+{"version":3,"file":"aiLabChat.d.ts","sourceRoot":"/","sources":["pipelines/aiLabChat.ts"],"names":[],"mappings":"AAOA,OAAO,KAAK,EAAE,UAAU,EAAE,KAAK,EAAE,IAAI,EAAE,OAAO,EAAE,IAAI,EAAE,MAAM,gBAAgB,CAAC;AAgD7E,wDAAwD;AACxD,KAAK,gBAAgB,GAAG;IACtB,KAAK,EAAE,KAAK,CAAC;IACb,QAAQ,EAAE,OAAO,EAAE,CAAC;IACpB,WAAW,EAAE;QAAE,EAAE,EAAE,MAAM,CAAC;QAAC,UAAU,EAAE,MAAM,CAAA;KAAE,EAAE,CAAC;IAClD,iBAAiB,EAAE;QAAE,EAAE,EAAE,MAAM,CAAC;QAAC,UAAU,EAAE,MAAM,CAAA;KAAE,EAAE,CAAC;IACxD,UAAU,EAAE;QAAE,EAAE,EAAE,MAAM,CAAC;QAAC,IAAI,EAAE,MAAM,CAAC;QAAC,aAAa,EAAE,MAAM,CAAA;KAAE,EAAE,CAAC;IAClE,KAAK,EAAE,IAAI,EAAE,CAAC;IACd,QAAQ,EAAE;QAAE,EAAE,EAAE,MAAM,CAAC;QAAC,QAAQ,EAAE,MAAM,CAAC;QAAC,OAAO,CAAC,EAAE;YAAE,WAAW,EAAE,MAAM,GAAG,IAAI,CAAA;SAAE,GAAG,IAAI,CAAA;KAAE,EAAE,CAAC;IAC9F,QAAQ,EAAE;QAAE,EAAE,EAAE,MAAM,CAAC;QAAC,QAAQ,EAAE,MAAM,CAAC;QAAC,OAAO,CAAC,EAAE;YAAE,WAAW,EAAE,MAAM,GAAG,IAAI,CAAA;SAAE,GAAG,IAAI,CAAA;KAAE,EAAE,CAAC;IAC9F,WAAW,EAAE,CAAC,UAAU,GAAG;QACzB,OAAO,CAAC,EAAE;YAAE,EAAE,EAAE,MAAM,CAAC;YAAC,IAAI,EAAE,MAAM,CAAC;YAAC,KAAK,CAAC,EAAE,MAAM,GAAG,IAAI,CAAA;SAAE,GAAG,IAAI,CAAC;QACrE,UAAU,CAAC,EAAE;YAAE,EAAE,EAAE,MAAM,CAAA;SAAE,GAAG,IAAI,CAAC;QACnC,eAAe,CAAC,EAAE;YAAE,EAAE,EAAE,MAAM,CAAA;SAAE,GAAG,IAAI,CAAC;KACzC,CAAC,EAAE,CAAC;CACN,CAAC;AAEF,KAAK,oBAAoB,GAAG;IAC1B,EAAE,EAAE,MAAM,CAAC;IACX,OAAO,EAAE,MAAM,CAAC;IAChB,QAAQ,EAAE,MAAM,CAAC;IACjB,SAAS,EAAE,IAAI,CAAC;IAChB,MAAM,EAAE;QACN,EAAE,EAAE,MAAM,CAAC;QACX,QAAQ,EAAE,MAAM,GAAG,IAAI,CAAC;QACxB,OAAO,EAAE;YACP,WAAW,EAAE,MAAM,GAAG,IAAI,CAAC;SAC5B,GAAG,IAAI,CAAC;KACV,GAAG,IAAI,CAAC;IACT,WAAW,EAAE;QACX,EAAE,EAAE,MAAM,CAAC;QACX,IAAI,EAAE,MAAM,CAAC;QACb,IAAI,EAAE,MAAM,CAAC;QACb,IAAI,EAAE,MAAM,CAAC;KACd,EAAE,CAAC;CACL,CAAC;AAEF;;;;GAIG;AACH,eAAO,MAAM,0BAA0B,GACrC,UAAU,oBAAoB,EAAE,EAChC,kBAAkB,MAAM,EACxB,cAAU,2BAYX,CAAC;AAwIF;;;GAGG;AACH,eAAO,MAAM,sBAAsB,GAAI,MAAM,gBAAgB,KAAG,MAsF/D,CAAC;AAEF;;GAEG;AACH,eAAO,MAAM,mBAAmB,GAC9B,SAAS,KAAK,EACd,SAAS,IAAI,EAAE,EACf,aAAa,UAAU,EAAE,EACzB,OAAO,IAAI,EAAE,EACb,UAAU,OAAO,EAAE,KAClB,MAYF,CAAC;AAIF;;;;;;GAMG;AACH,eAAO,MAAM,8BAA8B,GACvC,WAAW,MAAM,EACjB,gBAAgB,MAAM,EACtB,gBAAgB,MAAM,EACtB,UAAU,MAAM,EAChB,aAAa,MAAM,KAClB,OAAO,CAAC,IAAI,CAgBd,CAAA;AAED;;;;;;;;;;;;;GAaG;AACH,eAAO,MAAM,0BAA0B,GACrC,WAAW,MAAM,EACjB,gBAAgB,MAAM,EACtB,aAAa;IAAE,OAAO,EAAE,MAAM,CAAC;IAAC,WAAW,EAAE,MAAM,CAAA;CAAE,KACpD,OAAO,CAAC,IAAI,CA4Td,CAAA"}

package/dist/pipelines/aiLabChat.js

@@ -1,20 +1,22 @@
 /**
  * AI lab chat pipeline – generates lab introductions and responses.
- * Can create worksheets, sections, assignments, and PDF docs from AI output.
+ * Can create worksheets, sections, assignments, and generated files from AI output.
  */
 
-!function(){try{var e="undefined"!=typeof window?window:"undefined"!=typeof global?global:"undefined"!=typeof globalThis?globalThis:"undefined"!=typeof self?self:{},n=(new e.Error).stack;n&&(e._sentryDebugIds=e._sentryDebugIds||{},e._sentryDebugIds[n]="4bfeb1af-edc2-540a-acc7-d36c999b18a3")}catch(e){}}();
+!function(){try{var e="undefined"!=typeof window?window:"undefined"!=typeof global?global:"undefined"!=typeof globalThis?globalThis:"undefined"!=typeof self?self:{},n=(new e.Error).stack;n&&(e._sentryDebugIds=e._sentryDebugIds||{},e._sentryDebugIds[n]="d3703630-d937-5008-878a-ce235919a235")}catch(e){}}();
 import { isAIUser } from "../utils/aiUser.js";
 import { prisma } from "../lib/prisma.js";
-import { pusher, teacherChannel } from "../lib/pusher.js";
+import { pusher, chatChannel, teacherChannel } from "../lib/pusher.js";
 import { completePendingAIMessage, failPendingAIMessage, } from "../utils/inference.js";
 import { logger } from "../utils/logger.js";
-import { createPdf } from "../lib/jsonConversion.js";
 import { v4 } from "uuid";
-import { bucket } from "../lib/googleCloudStorage.js";
+import { bucket, getSignedUrl } from "../lib/googleCloudStorage.js";
+import { generateDocumentWithOpenAI } from "../services/openaiDocumentGen.js";
+import { inferDocumentFormat } from "../lib/inferDocumentFormat.js";
+import { normalizeDocumentFormat } from "../services/openaiDocumentGen.js";
 import { broadcastTextChunks, broadcastStreamComplete } from "../utils/streamBroadcast.js";
 import { buildLabChatAgentMessages } from "./labChatPrompt.js";
-import { streamChatResponse } from "../services/aiChatStream.js";
+import { applyResolvedFormatsToStreamParts, enrichStreamPartsWithGeneratedFiles, streamChatResponse, } from "../services/aiChatStream.js";
 import { aiTools } from "../services/aiTools.js";
 import { labProposalTools, createLabProposals } from "../services/aiProposalTools.js";
 /** Cap model wait time; leave headroom after inference for PDF/GCS/DB within Vercel maxDuration (500s). */
@@ -67,6 +69,14 @@ const loadRecentLabChatMessages = async (conversationId, anchorMessageId) => {
                 },
             },
         },
+        attachments: {
+            select: {
+                id: true,
+                name: true,
+                type: true,
+                path: true,
+            },
+        },
     };
     const newestMessages = await prisma.message.findMany({
         where: baseQuery,
@@ -126,6 +136,34 @@ const loadRecentLabChatMessages = async (conversationId, anchorMessageId) => {
     })
         .slice(0, limit);
 };
+/**
+ * Resolves signed URLs for image attachments in messages so the LLM can see them.
+ * Non-image files are passed as text descriptions only.
+ */
+async function resolveAttachmentUrls(messages) {
+    const resolved = [];
+    for (const msg of messages) {
+        const attachments = msg.attachments ?? [];
+        if (attachments.length === 0) {
+            resolved.push({ ...msg, attachments: [] });
+            continue;
+        }
+        const withUrls = await Promise.all(attachments.map(async (a) => {
+            if (a.type.startsWith('image/')) {
+                try {
+                    const url = await getSignedUrl(a.path);
+                    return { id: a.id, name: a.name, type: a.type, url };
+                }
+                catch {
+                    return { id: a.id, name: a.name, type: a.type };
+                }
+            }
+            return { id: a.id, name: a.name, type: a.type };
+        }));
+        resolved.push({ ...msg, attachments: withUrls });
+    }
+    return resolved;
+}
 /**
  * Builds schema-aware context for the AI from class data.
  * Formats entities with IDs so the model can reference them when creating assignments.
@@ -235,7 +273,7 @@ export const getBaseSystemPrompt = (context, members, assignments, files, sectio
  * COMPLETED with the intro content, or to FAILED on a hard error.
  */
 export const generateAndSendLabIntroduction = async (labChatId, conversationId, _contextString, _subject, aiMessageId) => {
-    const introMessage = "Hello teaching team! I'm your AI assistant for course material development. I'll help you create educational content - when you have a clear request, I'll produce it directly. I only ask questions when I need to clarify the topic or scope. What would you like to work on?";
+    const introMessage = "Hello teaching team! I'm your AI assistant for course material development. I can create worksheets, assignments, and downloadable files — PDFs, Word docs, PowerPoints, spreadsheets, and more. When you have a clear request, I'll produce it directly. I only ask questions when I need to clarify the topic or scope. What would you like to work on?";
     try {
         await broadcastTextChunks(conversationId, aiMessageId, introMessage);
         await completePendingAIMessage(aiMessageId, introMessage);
@@ -264,7 +302,7 @@ export const generateAndSendLabIntroduction = async (labChatId, conversationId,
  * conversation history is reloaded from the DB anchored on the AI
  * placeholder.
  */
-export const generateAndSendLabResponse = async (labChatId, _teacherMessage, emitOptions) => {
+export const generateAndSendLabResponse = async (labChatId, teacherMessage, emitOptions) => {
     try {
         // Get lab context from database
         const fullLabChat = await prisma.labChat.findUnique({
@@ -348,10 +386,12 @@ export const generateAndSendLabResponse = async (labChatId, _teacherMessage, emi
             teachers: classData.teachers,
             assignments: classData.assignments,
         });
+        // Resolve signed URLs for image attachments so the LLM can see them
+        const messagesWithAttachments = await resolveAttachmentUrls(recentMessages.reverse());
         const { system, messages } = buildLabChatAgentMessages({
             context: fullLabChat.context,
             classContext,
-            recentMessages: recentMessages.reverse(),
+            recentMessages: messagesWithAttachments,
             isAIUser,
         });
         // Genuine agentic generation: the model streams prose token-by-token and
@@ -363,7 +403,7 @@ export const generateAndSendLabResponse = async (labChatId, _teacherMessage, emi
             ...aiTools(fullLabChat.classId),
             ...labProposalTools(proposals),
         };
-        const { text: streamedText, parts: streamParts } = await withTimeout(streamChatResponse({
+        const { text: streamedText, parts: rawStreamParts } = await withTimeout(streamChatResponse({
             conversationId,
             aiMessageId: emitOptions.aiMessageId,
             system,
@@ -376,70 +416,108 @@ export const generateAndSendLabResponse = async (labChatId, _teacherMessage, emi
         // Real text + tool-call events were already broadcast inline (in order)
         // during the stream by `streamChatResponse`. Just close the stream.
         await broadcastStreamComplete(conversationId, emitOptions.aiMessageId);
-        // Generate PDFs for any proposed documents and persist the message.
+        // `generate_document` is an inline tool that only QUEUES into `proposals.docs`
+        // during the stream. OpenAI Code Interpreter renders files here, after the
+        // stream ends, then we link them to this message.
         try {
             const attachmentIds = [];
-            // Generate PDFs if docs were proposed
-            if (proposals.docs.length > 0) {
-                for (let i = 0; i < proposals.docs.length; i++) {
-                    const doc = proposals.docs[i];
-                    if (!doc.title || !doc.blocks || !Array.isArray(doc.blocks)) {
-                        logger.error(`Document ${i + 1} is missing title or blocks`);
-                        continue;
-                    }
-                    try {
-                        let pdfBytes = await createPdf(doc.blocks);
-                        if (pdfBytes) {
-                            // Sanitize filename - remove special characters and limit length
-                            const sanitizedTitle = doc.title
-                                .replace(/[^a-zA-Z0-9\s\-_]/g, '')
-                                .replace(/\s+/g, '_')
-                                .substring(0, 50);
-                            const filename = `${sanitizedTitle}_${v4().substring(0, 8)}.pdf`;
-                            const filePath = `class/generated/${fullLabChat.classId}/${filename}`;
-                            logger.info(`PDF ${i + 1} generated successfully`, { labChatId, title: doc.title });
-                            // Upload directly to Google Cloud Storage
-                            const gcsFile = bucket.file(filePath);
-                            await gcsFile.save(Buffer.from(pdfBytes), {
-                                metadata: {
-                                    contentType: 'application/pdf',
-                                }
-                            });
-                            logger.info(`PDF ${i + 1} uploaded successfully`, { labChatId, filename });
-                            const file = await prisma.file.create({
-                                data: {
-                                    name: filename,
-                                    path: filePath,
-                                    type: 'application/pdf',
-                                    size: pdfBytes.length,
-                                    userId: fullLabChat.createdById,
-                                    uploadStatus: 'COMPLETED',
-                                    uploadedAt: new Date(),
-                                },
-                            });
-                            attachmentIds.push(file.id);
-                        }
-                        else {
-                            logger.error(`PDF ${i + 1} creation returned undefined/null`, { labChatId, title: doc.title });
-                        }
-                    }
-                    catch (pdfError) {
-                        logger.error(`PDF creation threw an error for document ${i + 1}:`, {
-                            error: pdfError instanceof Error ? {
-                                message: pdfError.message,
-                                stack: pdfError.stack,
-                                name: pdfError.name
-                            } : pdfError,
+            const generatedDocFiles = [];
+            const resolvedDocs = [];
+            for (const doc of proposals.docs) {
+                if (!doc.title || !doc.content?.trim()) {
+                    logger.error('Document missing title or content', { labChatId, doc });
+                    continue;
+                }
+                const format = inferDocumentFormat(doc.title, doc.content, doc.format, teacherMessage);
+                resolvedDocs.push({ title: doc.title, format });
+                if (format !== normalizeDocumentFormat(doc.format)) {
+                    logger.info('Document format overridden from model default', {
+                        labChatId,
+                        title: doc.title,
+                        modelFormat: doc.format,
+                        resolvedFormat: format,
+                    });
+                }
+                try {
+                    const generated = await generateDocumentWithOpenAI({
+                        title: doc.title,
+                        content: doc.content,
+                        format,
+                    });
+                    if (!generated) {
+                        logger.error('OpenAI document generation returned null', {
                             labChatId,
-                            title: doc.title
+                            title: doc.title,
+                            format: doc.format,
                         });
+                        continue;
                     }
+                    const sanitizedTitle = doc.title
+                        .replace(/[^a-zA-Z0-9\s\-_]/g, '')
+                        .replace(/\s+/g, '_')
+                        .substring(0, 50);
+                    const filename = `${sanitizedTitle}_${v4().substring(0, 8)}.${generated.format}`;
+                    const filePath = `class/generated/${fullLabChat.classId}/${filename}`;
+                    await bucket.file(filePath).save(generated.bytes, {
+                        metadata: { contentType: generated.mimeType },
+                    });
+                    const file = await prisma.file.create({
+                        data: {
+                            name: filename,
+                            path: filePath,
+                            type: generated.mimeType,
+                            size: generated.bytes.length,
+                            userId: fullLabChat.createdById,
+                            conversationId,
+                            messageId: emitOptions.aiMessageId,
+                            uploadStatus: 'COMPLETED',
+                            uploadedAt: new Date(),
+                        },
+                    });
+                    attachmentIds.push(file.id);
+                    generatedDocFiles.push({
+                        title: doc.title,
+                        fileId: file.id,
+                        fileName: filename,
+                        format: generated.format,
+                    });
+                }
+                catch (docError) {
+                    logger.error('Document generation failed', {
+                        error: docError instanceof Error ? {
+                            message: docError.message,
+                            stack: docError.stack,
+                            name: docError.name,
+                        } : docError,
+                        labChatId,
+                        title: doc.title,
+                        format: doc.format,
+                    });
+                }
+            }
+            const streamParts = enrichStreamPartsWithGeneratedFiles(applyResolvedFormatsToStreamParts(rawStreamParts, resolvedDocs), generatedDocFiles);
+            for (const part of streamParts) {
+                if (part.type === 'tool' &&
+                    part.toolName === 'generate_document' &&
+                    part.fileId) {
+                    await pusher
+                        .trigger(chatChannel(conversationId), 'message-tool-call', {
+                        messageId: emitOptions.aiMessageId,
+                        toolCallId: part.toolCallId,
+                        toolName: part.toolName,
+                        ...(part.title ? { title: part.title } : {}),
+                        ...(part.format ? { format: part.format } : {}),
+                        fileId: part.fileId,
+                        fileName: part.fileName,
+                        status: 'completed',
+                    })
+                        .catch(() => { });
                 }
             }
             await completePendingAIMessage(emitOptions.aiMessageId, streamedText, {
-                attachments: {
-                    connect: attachmentIds.map(id => ({ id })),
-                },
+                ...(attachmentIds.length > 0 && {
+                    attachments: { connect: attachmentIds.map((id) => ({ id })) },
+                }),
                 meta: {
                     assignmentsToCreate: proposals.assignments.length > 0
                         ? proposals.assignments.map(assignment => ({ ...assignment, id: v4() }))
@@ -499,4 +577,4 @@ export const generateAndSendLabResponse = async (labChatId, _teacherMessage, emi
     }
 };
 //# sourceMappingURL=aiLabChat.js.map
-//# debugId=4bfeb1af-edc2-540a-acc7-d36c999b18a3
+//# debugId=d3703630-d937-5008-878a-ce235919a235

package/dist/pipelines/aiLabChat.js.map

@@ -1 +1 @@
-{"version":3,"file":"aiLabChat.js","sources":["pipelines/aiLabChat.ts"],"sourceRoot":"/","sourcesContent":["/**\n * AI lab chat pipeline – generates lab introductions and responses.\n * Can create worksheets, sections, assignments, and PDF docs from AI output.\n */\nimport { isAIUser } from \"../utils/aiUser.js\";\nimport { prisma } from \"../lib/prisma.js\";\nimport { pusher, teacherChannel } from \"../lib/pusher.js\";\nimport type { Assignment, Class, File, Section, User } from \"@prisma/client\";\nimport {\n  completePendingAIMessage,\n  failPendingAIMessage,\n} from \"../utils/inference.js\";\nimport { logger } from \"../utils/logger.js\";\nimport { createPdf } from \"../lib/jsonConversion.js\";\nimport { v4 } from \"uuid\";\nimport { bucket } from \"../lib/googleCloudStorage.js\";\nimport { DocumentBlock } from \"../lib/jsonStyles.js\";\nimport { broadcastTextChunks, broadcastStreamComplete } from \"../utils/streamBroadcast.js\";\nimport { buildLabChatAgentMessages } from \"./labChatPrompt.js\";\nimport { streamChatResponse } from \"../services/aiChatStream.js\";\nimport { aiTools } from \"../services/aiTools.js\";\nimport { labProposalTools, createLabProposals } from \"../services/aiProposalTools.js\";\n\n/** Cap model wait time; leave headroom after inference for PDF/GCS/DB within Vercel maxDuration (500s). */\nconst LAB_CHAT_RESPONSE_TIMEOUT_MS = 400_000;\n\nconst withTimeout = async <T>(\n  task: Promise<T>,\n  timeoutMs: number,\n  operationName: string,\n): Promise<T> => {\n  let timeoutHandle: NodeJS.Timeout | undefined;\n  const timeoutPromise = new Promise<never>((_, reject) => {\n    timeoutHandle = setTimeout(() => {\n      reject(new Error(`${operationName} timed out after ${timeoutMs}ms`));\n    }, timeoutMs);\n  });\n\n  try {\n    return await Promise.race([task, timeoutPromise]);\n  } finally {\n    if (timeoutHandle) {\n      clearTimeout(timeoutHandle);\n    }\n  }\n};\n\n/** Extended class data for AI context (schema-aware) */\ntype ClassContextData = {\n  class: Class;\n  sections: Section[];\n  markSchemes: { id: string; structured: string }[];\n  gradingBoundaries: { id: string; structured: string }[];\n  worksheets: { id: string; name: string; questionCount: number }[];\n  files: File[];\n  students: { id: string; username: string; profile?: { displayName: string | null } | null }[];\n  teachers: { id: string; username: string; profile?: { displayName: string | null } | null }[];\n  assignments: (Assignment & {\n    section?: { id: string; name: string; order?: number | null } | null;\n    markScheme?: { id: string } | null;\n    gradingBoundary?: { id: string } | null;\n  })[];\n};\n\ntype RecentLabChatMessage = {\n  id: string;\n  content: string;\n  senderId: string;\n  createdAt: Date;\n  sender: {\n    id: string;\n    username: string | null;\n    profile: {\n      displayName: string | null;\n    } | null;\n  } | null;\n};\n\n/**\n * `messages` must be ordered newest-first.\n * When `anchorMessageId` is provided, `sliceMessagesThroughAnchor` returns the\n * anchor message and older messages only, capped to `limit`.\n */\nexport const sliceMessagesThroughAnchor = (\n  messages: RecentLabChatMessage[],\n  anchorMessageId?: string,\n  limit = 10,\n) => {\n  if (!anchorMessageId) {\n    return messages.slice(0, limit);\n  }\n\n  const anchorIndex = messages.findIndex((message) => message.id === anchorMessageId);\n  if (anchorIndex === -1) {\n    return messages.slice(0, limit);\n  }\n\n  return messages.slice(anchorIndex, anchorIndex + limit);\n};\n\nconst loadRecentLabChatMessages = async (\n  conversationId: string,\n  anchorMessageId?: string,\n): Promise<RecentLabChatMessage[]> => {\n  const limit = 10;\n  const baseQuery = {\n    conversationId,\n  };\n  const include = {\n    sender: {\n      select: {\n        id: true,\n        username: true,\n        profile: {\n          select: {\n            displayName: true,\n          },\n        },\n      },\n    },\n  };\n\n  const newestMessages = await prisma.message.findMany({\n    where: baseQuery,\n    include,\n    orderBy: {\n      createdAt: 'desc',\n    },\n    take: 25,\n  });\n\n  const anchoredMessages = sliceMessagesThroughAnchor(newestMessages, anchorMessageId, limit);\n  if (!anchorMessageId || anchoredMessages.some((message) => message.id === anchorMessageId)) {\n    return anchoredMessages;\n  }\n\n  const anchorMessage = await prisma.message.findUnique({\n    where: { id: anchorMessageId },\n    include,\n  });\n\n  if (!anchorMessage) {\n    throw new Error(`Anchor message ${anchorMessageId} not found`);\n  }\n\n  if (anchorMessage.conversationId !== conversationId) {\n    throw new Error(`Anchor message ${anchorMessageId} does not belong to conversation ${conversationId}`);\n  }\n\n  const olderMessages = await prisma.message.findMany({\n    where: {\n      conversationId,\n      createdAt: {\n        lte: anchorMessage.createdAt,\n      },\n    },\n    include,\n    orderBy: {\n      createdAt: 'desc',\n    },\n    take: limit,\n  });\n\n  const dedupedMessages = new Map<string, RecentLabChatMessage>();\n  dedupedMessages.set(anchorMessage.id, anchorMessage);\n\n  olderMessages.forEach((message) => {\n    if (!dedupedMessages.has(message.id)) {\n      dedupedMessages.set(message.id, message);\n    }\n  });\n\n  return Array.from(dedupedMessages.values())\n    .sort((left, right) => {\n      const timeDelta = right.createdAt.getTime() - left.createdAt.getTime();\n      if (timeDelta !== 0) {\n        return timeDelta;\n      }\n      if (left.id === anchorMessage.id) {\n        return -1;\n      }\n      if (right.id === anchorMessage.id) {\n        return 1;\n      }\n\n      return right.id.localeCompare(left.id);\n    })\n    .slice(0, limit);\n};\n\n/**\n * Builds schema-aware context for the AI from class data.\n * Formats entities with IDs so the model can reference them when creating assignments.\n */\nexport const buildClassContextForAI = (data: ClassContextData): string => {\n  const { class: cls, sections, markSchemes, gradingBoundaries, worksheets, files, students, assignments } = data;\n\n  const sectionList = sections\n    .sort((a, b) => (a.order ?? 999) - (b.order ?? 999))\n    .map((s) => `  - id: ${s.id} | name: \"${s.name}\" | color: ${s.color ?? \"default\"}`)\n    .join(\"\\n\");\n\n  const markSchemeList = markSchemes\n    .map((ms) => {\n      let preview = \"structured rubric\";\n      try {\n        const parsed = JSON.parse(ms.structured || \"{}\");\n        preview = parsed.name || Object.keys(parsed).slice(0, 2).join(\", \") || \"rubric\";\n      } catch {\n        /* ignore */\n      }\n      return `  - id: ${ms.id} | ${preview}`;\n    })\n    .join(\"\\n\");\n\n  const gradingBoundaryList = gradingBoundaries\n    .map((gb) => {\n      let preview = \"grading scale\";\n      try {\n        const parsed = JSON.parse(gb.structured || \"{}\");\n        preview = parsed.name || Object.keys(parsed).slice(0, 2).join(\", \") || \"scale\";\n      } catch {\n        /* ignore */\n      }\n      return `  - id: ${gb.id} | ${preview}`;\n    })\n    .join(\"\\n\");\n\n  const worksheetList = worksheets\n    .map((w) => `  - id: ${w.id} | name: \"${w.name}\" | questions: ${w.questionCount}`)\n    .join(\"\\n\");\n\n  const fileList = files\n    .filter((f) => f.type === \"application/pdf\" || f.type?.includes(\"document\"))\n    .map((f) => `  - id: ${f.id} | name: \"${f.name}\" | type: ${f.type}`)\n    .join(\"\\n\");\n  const otherFiles = files.filter((f) => f.type !== \"application/pdf\" && !f.type?.includes(\"document\"));\n  const otherFileList = otherFiles.length\n    ? otherFiles.map((f) => `  - id: ${f.id} | name: \"${f.name}\"`).join(\"\\n\")\n    : \"  (none)\";\n\n  const studentList = students\n    .map((u) => `  - id: ${u.id} | username: ${u.username} | displayName: ${u.profile?.displayName ?? \"—\"}`)\n    .join(\"\\n\");\n\n  const assignmentSummary = assignments\n    .map((a) => {\n      const sectionName = a.section?.name ?? \"—\";\n      return `  - id: ${a.id} | title: \"${a.title}\" | type: ${a.type} | section: \"${sectionName}\" | due: ${a.dueDate.toISOString().slice(0, 10)}`;\n    })\n    .join(\"\\n\");\n\n  return `\nCLASS: ${cls.name} | Subject: ${cls.subject} | Section: ${cls.section}\nSyllabus: ${cls.syllabus ? cls.syllabus.slice(0, 200) + (cls.syllabus.length > 200 ? \"…\" : \"\") : \"(none)\"}\n\nSECTIONS (use sectionId when creating assignments):\n${sectionList || \"  (none - suggest sectionsToCreate first)\"}\n\nMARK SCHEMES (use markSchemeId when creating assignments):\n${markSchemeList || \"  (none - suggest creating one or omit markSchemeId)\"}\n\nGRADING BOUNDARIES (use gradingBoundaryId when creating assignments):\n${gradingBoundaryList || \"  (none - suggest creating one or omit gradingBoundaryId)\"}\n\nWORKSHEETS (use worksheetIds when acceptWorksheet is true):\n${worksheetList || \"  (none - use worksheetsToCreate or create via docs first)\"}\n\nFILES - PDFs/Documents (for assignment attachments):\n${fileList || \"  (none)\"}\n\nFILES - Other (for assignment attachments):\n${otherFileList}\n\nSTUDENTS (use studentIds for specific assignment; empty array = all students):\n${studentList || \"  (none)\"}\n\nEXISTING ASSIGNMENTS (for reference, avoid duplicates):\n${assignmentSummary || \"  (none)\"}\n`.trim();\n};\n\n/**\n * @deprecated Use buildClassContextForAI for schema-aware context. Kept for compatibility.\n */\nexport const getBaseSystemPrompt = (\n  context: Class,\n  members: User[],\n  assignments: Assignment[],\n  files: File[],\n  sections: Section[]\n): string => {\n  return buildClassContextForAI({\n    class: context,\n    sections,\n    markSchemes: [],\n    gradingBoundaries: [],\n    worksheets: [],\n    files,\n    students: members,\n    teachers: [],\n    assignments,\n  });\n};\n\n\n\n/**\n * Fill the AI introduction placeholder for a brand-new lab chat.\n *\n * The caller (service layer) must have already created a PENDING AI Message\n * row — `aiMessageId` is that placeholder. This function flips it to\n * COMPLETED with the intro content, or to FAILED on a hard error.\n */\nexport const generateAndSendLabIntroduction = async (\n    labChatId: string,\n    conversationId: string,\n    _contextString: string,\n    _subject: string,\n    aiMessageId: string,\n  ): Promise<void> => {\n    const introMessage =\n      \"Hello teaching team! I'm your AI assistant for course material development. I'll help you create educational content - when you have a clear request, I'll produce it directly. I only ask questions when I need to clarify the topic or scope. What would you like to work on?\";\n\n    try {\n      await broadcastTextChunks(conversationId, aiMessageId, introMessage);\n      await completePendingAIMessage(aiMessageId, introMessage);\n      logger.info('AI Introduction sent', { labChatId, conversationId, aiMessageId });\n    } catch (error) {\n      logger.error('Failed to complete AI introduction placeholder:', {\n        error,\n        labChatId,\n        aiMessageId,\n      });\n      await failPendingAIMessage(aiMessageId, { reason: 'lab_intro_complete_failed' });\n    }\n  }\n  \n  /**\n   * Fill the AI response placeholder for a teacher reply in a lab chat.\n   *\n   * `aiMessageId` is the PENDING AI Message row created by the service\n   * layer; the pipeline flips it to COMPLETED with content / attachments /\n   * meta, or FAILED on error.  Teacher-channel `lab-response-{pending,\n   * completed,failed}` events fire alongside the chat-channel status flips\n   * (which `completePendingAIMessage` / `failPendingAIMessage` already\n   * broadcast) so the lab list \"AI busy\" indicator stays accurate.\n   *\n   * `_teacherMessage` is retained for caller compatibility — the actual\n   * conversation history is reloaded from the DB anchored on the AI\n   * placeholder.\n   */\n  export const generateAndSendLabResponse = async (\n    labChatId: string,\n    _teacherMessage: string,\n    emitOptions: { classId: string; aiMessageId: string }\n  ): Promise<void> => {\n    try {\n      // Get lab context from database\n      const fullLabChat = await prisma.labChat.findUnique({\n        where: { id: labChatId },\n        include: {\n          class: {\n            select: {\n              name: true,\n              subject: true,\n            },\n          },\n        },\n      });\n  \n      if (!fullLabChat) {\n        throw new Error('Lab chat not found');\n      }\n  \n      const conversationId = fullLabChat.conversationId;\n  \n      // Anchor history on the AI placeholder — the slice will include the\n      // placeholder itself (empty content) at the top; drop it so the model\n      // does not see an empty assistant turn at the very end.\n      const anchoredMessages = await loadRecentLabChatMessages(\n        conversationId,\n        emitOptions.aiMessageId,\n      );\n      const recentMessages = anchoredMessages.filter(\n        (msg) => msg.id !== emitOptions.aiMessageId,\n      );\n  \n      const classData = await prisma.class.findUnique({\n        where: {\n          id: fullLabChat.classId,\n        },\n        include: {\n          assignments: {\n            include: {\n              section: { select: { id: true, name: true, order: true } },\n              markScheme: { select: { id: true } },\n              gradingBoundary: { select: { id: true } },\n            },\n          },\n          sections: true,\n          markSchemes: { select: { id: true, structured: true } },\n          gradingBoundaries: { select: { id: true, structured: true } },\n          worksheets: {\n            select: {\n              id: true,\n              name: true,\n              _count: { select: { questions: true } },\n            },\n          },\n          students: {\n            select: {\n              id: true,\n              username: true,\n              profile: { select: { displayName: true } },\n            },\n          },\n          teachers: {\n            select: {\n              id: true,\n              username: true,\n              profile: { select: { displayName: true } },\n            },\n          },\n          classFiles: {\n            include: {\n              files: true,\n            },\n          },\n        },\n      });\n\n      if (!classData) {\n        throw new Error('Class not found');\n      }\n\n      const classContext = buildClassContextForAI({\n        class: classData,\n        sections: classData.sections,\n        markSchemes: classData.markSchemes,\n        gradingBoundaries: classData.gradingBoundaries,\n        worksheets: classData.worksheets.map((w) => ({\n          id: w.id,\n          name: w.name,\n          questionCount: w._count.questions,\n        })),\n        files: classData.classFiles?.files ?? [],\n        students: classData.students,\n        teachers: classData.teachers,\n        assignments: classData.assignments,\n      });\n\n      const { system, messages } = buildLabChatAgentMessages({\n        context: fullLabChat.context,\n        classContext,\n        recentMessages: recentMessages.reverse(),\n        isAIUser,\n      });\n\n      // Genuine agentic generation: the model streams prose token-by-token and\n      // calls real tools inline — read-only RAG lookups plus \"propose_*\" tools\n      // that record create-actions into `proposals`. `streamChatResponse`\n      // broadcasts the real text chunks and tool-call events as they happen.\n      const proposals = createLabProposals();\n      const tools = {\n        ...aiTools(fullLabChat.classId),\n        ...labProposalTools(proposals),\n      };\n\n      const { text: streamedText, parts: streamParts } = await withTimeout(\n        streamChatResponse({\n          conversationId,\n          aiMessageId: emitOptions.aiMessageId,\n          system,\n          messages,\n          tools,\n          temperature: 0.7,\n          maxOutputTokens: 4096,\n          maxSteps: 8,\n        }),\n        LAB_CHAT_RESPONSE_TIMEOUT_MS,\n        \"Lab chat response generation\",\n      );\n\n      // Real text + tool-call events were already broadcast inline (in order)\n      // during the stream by `streamChatResponse`. Just close the stream.\n      await broadcastStreamComplete(conversationId, emitOptions.aiMessageId);\n\n      // Generate PDFs for any proposed documents and persist the message.\n      try {\n        const attachmentIds: string[] = [];\n        // Generate PDFs if docs were proposed\n        if (proposals.docs.length > 0) {\n          \n  \n          for (let i = 0; i < proposals.docs.length; i++) {\n            const doc = proposals.docs[i];\n            if (!doc.title || !doc.blocks || !Array.isArray(doc.blocks)) {\n              logger.error(`Document ${i + 1} is missing title or blocks`);\n              continue;\n            } \n  \n  \n            try {\n              let pdfBytes = await createPdf(doc.blocks as DocumentBlock[]);            \n              if (pdfBytes) {\n                // Sanitize filename - remove special characters and limit length\n                const sanitizedTitle = doc.title\n                  .replace(/[^a-zA-Z0-9\\s\\-_]/g, '')\n                  .replace(/\\s+/g, '_')\n                  .substring(0, 50);\n                \n                const filename = `${sanitizedTitle}_${v4().substring(0, 8)}.pdf`;\n                const filePath = `class/generated/${fullLabChat.classId}/${filename}`;\n  \n                logger.info(`PDF ${i + 1} generated successfully`, { labChatId, title: doc.title });\n                \n                // Upload directly to Google Cloud Storage\n                const gcsFile = bucket.file(filePath);\n                await gcsFile.save(Buffer.from(pdfBytes), {\n                  metadata: {\n                    contentType: 'application/pdf',\n                  }\n                });\n      \n                logger.info(`PDF ${i + 1} uploaded successfully`, { labChatId, filename });\n  \n                const file = await prisma.file.create({\n                  data: {\n                    name: filename,\n                    path: filePath,\n                    type: 'application/pdf',\n                    size: pdfBytes.length,\n                    userId: fullLabChat.createdById,\n                    uploadStatus: 'COMPLETED',\n                    uploadedAt: new Date(),\n                  },\n                });\n                attachmentIds.push(file.id);\n              } else {\n                logger.error(`PDF ${i + 1} creation returned undefined/null`, { labChatId, title: doc.title });\n              }\n            } catch (pdfError) {\n              logger.error(`PDF creation threw an error for document ${i + 1}:`, { \n                error: pdfError instanceof Error ? {\n                  message: pdfError.message,\n                  stack: pdfError.stack,\n                  name: pdfError.name\n                } : pdfError, \n                labChatId,\n                title: doc.title\n              });\n            }\n          }\n        }\n  \n        await completePendingAIMessage(emitOptions.aiMessageId, streamedText, {\n          attachments: {\n            connect: attachmentIds.map(id => ({ id })),\n          },\n          meta: {\n            assignmentsToCreate: proposals.assignments.length > 0\n              ? proposals.assignments.map(assignment => ({ ...assignment, id: v4() }))\n              : null,\n            worksheetsToCreate: proposals.worksheets.length > 0\n              ? proposals.worksheets.map(worksheet => ({ ...worksheet, id: v4() }))\n              : null,\n            sectionsToCreate: proposals.sections.length > 0\n              ? proposals.sections.map(section => ({ ...section, id: v4() }))\n              : null,\n            streamParts: streamParts.length > 0 ? streamParts : null,\n          },\n        });\n      } catch (persistError) {\n        logger.error('Failed to persist AI response or generate PDF:', { error: persistError, labChatId });\n        // Fallback: complete the placeholder with the raw text so the\n        // teacher still sees something useful instead of FAILED.\n        await completePendingAIMessage(emitOptions.aiMessageId, streamedText);\n      }\n\n      try {\n        await pusher.trigger(teacherChannel(emitOptions.classId), \"lab-response-completed\", {\n          labChatId,\n          messageId: emitOptions.aiMessageId,\n        });\n      } catch (broadcastError) {\n        logger.error(\"Failed to broadcast lab response completed:\", { error: broadcastError });\n      }\n\n      logger.info('AI response sent', { labChatId, conversationId, aiMessageId: emitOptions.aiMessageId });\n\n    } catch (error) {\n      console.error('Full error object:', error);\n      logger.error('Failed to generate AI response:', {\n        error: error instanceof Error ? {\n          message: error.message,\n          stack: error.stack,\n          name: error.name\n        } : error,\n        labChatId,\n        aiMessageId: emitOptions.aiMessageId,\n      });\n\n      await failPendingAIMessage(emitOptions.aiMessageId, {\n        reason: 'lab_response_generation_failed',\n      });\n\n      try {\n        await pusher.trigger(teacherChannel(emitOptions.classId), \"lab-response-failed\", {\n          labChatId,\n          messageId: emitOptions.aiMessageId,\n          error: \"AI response generation failed\",\n        });\n      } catch (broadcastError) {\n        logger.error(\"Failed to broadcast lab response failed:\", { error: broadcastError });\n      }\n\n      throw error; // Re-throw to see the full error in the calling function\n    }\n  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+{"version":3,"file":"aiLabChat.js","sources":["pipelines/aiLabChat.ts"],"sourceRoot":"/","sourcesContent":["/**\n * AI lab chat pipeline – generates lab introductions and responses.\n * Can create worksheets, sections, assignments, and generated files from AI output.\n */\nimport { isAIUser } from \"../utils/aiUser.js\";\nimport { prisma } from \"../lib/prisma.js\";\nimport { pusher, chatChannel, teacherChannel } from \"../lib/pusher.js\";\nimport type { Assignment, Class, File, Section, User } from \"@prisma/client\";\nimport {\n  completePendingAIMessage,\n  failPendingAIMessage,\n} from \"../utils/inference.js\";\nimport { logger } from \"../utils/logger.js\";\nimport { v4 } from \"uuid\";\nimport { bucket, getSignedUrl } from \"../lib/googleCloudStorage.js\";\nimport { generateDocumentWithOpenAI } from \"../services/openaiDocumentGen.js\";\nimport { inferDocumentFormat } from \"../lib/inferDocumentFormat.js\";\nimport { normalizeDocumentFormat } from \"../services/openaiDocumentGen.js\";\nimport { broadcastTextChunks, broadcastStreamComplete } from \"../utils/streamBroadcast.js\";\nimport { buildLabChatAgentMessages } from \"./labChatPrompt.js\";\nimport type { ConversationMessage } from \"./labChatPrompt.js\";\nimport {\n  applyResolvedFormatsToStreamParts,\n  enrichStreamPartsWithGeneratedFiles,\n  streamChatResponse,\n  type GeneratedDocFileLink,\n  type StreamPart,\n} from \"../services/aiChatStream.js\";\nimport { aiTools } from \"../services/aiTools.js\";\nimport { labProposalTools, createLabProposals } from \"../services/aiProposalTools.js\";\n\n/** Cap model wait time; leave headroom after inference for PDF/GCS/DB within Vercel maxDuration (500s). */\nconst LAB_CHAT_RESPONSE_TIMEOUT_MS = 400_000;\n\nconst withTimeout = async <T>(\n  task: Promise<T>,\n  timeoutMs: number,\n  operationName: string,\n): Promise<T> => {\n  let timeoutHandle: NodeJS.Timeout | undefined;\n  const timeoutPromise = new Promise<never>((_, reject) => {\n    timeoutHandle = setTimeout(() => {\n      reject(new Error(`${operationName} timed out after ${timeoutMs}ms`));\n    }, timeoutMs);\n  });\n\n  try {\n    return await Promise.race([task, timeoutPromise]);\n  } finally {\n    if (timeoutHandle) {\n      clearTimeout(timeoutHandle);\n    }\n  }\n};\n\n/** Extended class data for AI context (schema-aware) */\ntype ClassContextData = {\n  class: Class;\n  sections: Section[];\n  markSchemes: { id: string; structured: string }[];\n  gradingBoundaries: { id: string; structured: string }[];\n  worksheets: { id: string; name: string; questionCount: number }[];\n  files: File[];\n  students: { id: string; username: string; profile?: { displayName: string | null } | null }[];\n  teachers: { id: string; username: string; profile?: { displayName: string | null } | null }[];\n  assignments: (Assignment & {\n    section?: { id: string; name: string; order?: number | null } | null;\n    markScheme?: { id: string } | null;\n    gradingBoundary?: { id: string } | null;\n  })[];\n};\n\ntype RecentLabChatMessage = {\n  id: string;\n  content: string;\n  senderId: string;\n  createdAt: Date;\n  sender: {\n    id: string;\n    username: string | null;\n    profile: {\n      displayName: string | null;\n    } | null;\n  } | null;\n  attachments: {\n    id: string;\n    name: string;\n    type: string;\n    path: string;\n  }[];\n};\n\n/**\n * `messages` must be ordered newest-first.\n * When `anchorMessageId` is provided, `sliceMessagesThroughAnchor` returns the\n * anchor message and older messages only, capped to `limit`.\n */\nexport const sliceMessagesThroughAnchor = (\n  messages: RecentLabChatMessage[],\n  anchorMessageId?: string,\n  limit = 10,\n) => {\n  if (!anchorMessageId) {\n    return messages.slice(0, limit);\n  }\n\n  const anchorIndex = messages.findIndex((message) => message.id === anchorMessageId);\n  if (anchorIndex === -1) {\n    return messages.slice(0, limit);\n  }\n\n  return messages.slice(anchorIndex, anchorIndex + limit);\n};\n\nconst loadRecentLabChatMessages = async (\n  conversationId: string,\n  anchorMessageId?: string,\n): Promise<RecentLabChatMessage[]> => {\n  const limit = 10;\n  const baseQuery = {\n    conversationId,\n  };\n  const include = {\n    sender: {\n      select: {\n        id: true,\n        username: true,\n        profile: {\n          select: {\n            displayName: true,\n          },\n        },\n      },\n    },\n    attachments: {\n      select: {\n        id: true,\n        name: true,\n        type: true,\n        path: true,\n      },\n    },\n  };\n\n  const newestMessages = await prisma.message.findMany({\n    where: baseQuery,\n    include,\n    orderBy: {\n      createdAt: 'desc',\n    },\n    take: 25,\n  });\n\n  const anchoredMessages = sliceMessagesThroughAnchor(newestMessages, anchorMessageId, limit);\n  if (!anchorMessageId || anchoredMessages.some((message) => message.id === anchorMessageId)) {\n    return anchoredMessages;\n  }\n\n  const anchorMessage = await prisma.message.findUnique({\n    where: { id: anchorMessageId },\n    include,\n  });\n\n  if (!anchorMessage) {\n    throw new Error(`Anchor message ${anchorMessageId} not found`);\n  }\n\n  if (anchorMessage.conversationId !== conversationId) {\n    throw new Error(`Anchor message ${anchorMessageId} does not belong to conversation ${conversationId}`);\n  }\n\n  const olderMessages = await prisma.message.findMany({\n    where: {\n      conversationId,\n      createdAt: {\n        lte: anchorMessage.createdAt,\n      },\n    },\n    include,\n    orderBy: {\n      createdAt: 'desc',\n    },\n    take: limit,\n  });\n\n  const dedupedMessages = new Map<string, RecentLabChatMessage>();\n  dedupedMessages.set(anchorMessage.id, anchorMessage);\n\n  olderMessages.forEach((message) => {\n    if (!dedupedMessages.has(message.id)) {\n      dedupedMessages.set(message.id, message);\n    }\n  });\n\n  return Array.from(dedupedMessages.values())\n    .sort((left, right) => {\n      const timeDelta = right.createdAt.getTime() - left.createdAt.getTime();\n      if (timeDelta !== 0) {\n        return timeDelta;\n      }\n      if (left.id === anchorMessage.id) {\n        return -1;\n      }\n      if (right.id === anchorMessage.id) {\n        return 1;\n      }\n\n      return right.id.localeCompare(left.id);\n    })\n    .slice(0, limit);\n};\n\n/**\n * Resolves signed URLs for image attachments in messages so the LLM can see them.\n * Non-image files are passed as text descriptions only.\n */\nasync function resolveAttachmentUrls(\n  messages: RecentLabChatMessage[],\n): Promise<ConversationMessage[]> {\n  const resolved: ConversationMessage[] = [];\n\n  for (const msg of messages) {\n    const attachments = msg.attachments ?? [];\n    if (attachments.length === 0) {\n      resolved.push({ ...msg, attachments: [] });\n      continue;\n    }\n\n    const withUrls = await Promise.all(\n      attachments.map(async (a) => {\n        if (a.type.startsWith('image/')) {\n          try {\n            const url = await getSignedUrl(a.path);\n            return { id: a.id, name: a.name, type: a.type, url };\n          } catch {\n            return { id: a.id, name: a.name, type: a.type };\n          }\n        }\n        return { id: a.id, name: a.name, type: a.type };\n      }),\n    );\n\n    resolved.push({ ...msg, attachments: withUrls });\n  }\n\n  return resolved;\n}\n\n/**\n * Builds schema-aware context for the AI from class data.\n * Formats entities with IDs so the model can reference them when creating assignments.\n */\nexport const buildClassContextForAI = (data: ClassContextData): string => {\n  const { class: cls, sections, markSchemes, gradingBoundaries, worksheets, files, students, assignments } = data;\n\n  const sectionList = sections\n    .sort((a, b) => (a.order ?? 999) - (b.order ?? 999))\n    .map((s) => `  - id: ${s.id} | name: \"${s.name}\" | color: ${s.color ?? \"default\"}`)\n    .join(\"\\n\");\n\n  const markSchemeList = markSchemes\n    .map((ms) => {\n      let preview = \"structured rubric\";\n      try {\n        const parsed = JSON.parse(ms.structured || \"{}\");\n        preview = parsed.name || Object.keys(parsed).slice(0, 2).join(\", \") || \"rubric\";\n      } catch {\n        /* ignore */\n      }\n      return `  - id: ${ms.id} | ${preview}`;\n    })\n    .join(\"\\n\");\n\n  const gradingBoundaryList = gradingBoundaries\n    .map((gb) => {\n      let preview = \"grading scale\";\n      try {\n        const parsed = JSON.parse(gb.structured || \"{}\");\n        preview = parsed.name || Object.keys(parsed).slice(0, 2).join(\", \") || \"scale\";\n      } catch {\n        /* ignore */\n      }\n      return `  - id: ${gb.id} | ${preview}`;\n    })\n    .join(\"\\n\");\n\n  const worksheetList = worksheets\n    .map((w) => `  - id: ${w.id} | name: \"${w.name}\" | questions: ${w.questionCount}`)\n    .join(\"\\n\");\n\n  const fileList = files\n    .filter((f) => f.type === \"application/pdf\" || f.type?.includes(\"document\"))\n    .map((f) => `  - id: ${f.id} | name: \"${f.name}\" | type: ${f.type}`)\n    .join(\"\\n\");\n  const otherFiles = files.filter((f) => f.type !== \"application/pdf\" && !f.type?.includes(\"document\"));\n  const otherFileList = otherFiles.length\n    ? otherFiles.map((f) => `  - id: ${f.id} | name: \"${f.name}\"`).join(\"\\n\")\n    : \"  (none)\";\n\n  const studentList = students\n    .map((u) => `  - id: ${u.id} | username: ${u.username} | displayName: ${u.profile?.displayName ?? \"—\"}`)\n    .join(\"\\n\");\n\n  const assignmentSummary = assignments\n    .map((a) => {\n      const sectionName = a.section?.name ?? \"—\";\n      return `  - id: ${a.id} | title: \"${a.title}\" | type: ${a.type} | section: \"${sectionName}\" | due: ${a.dueDate.toISOString().slice(0, 10)}`;\n    })\n    .join(\"\\n\");\n\n  return `\nCLASS: ${cls.name} | Subject: ${cls.subject} | Section: ${cls.section}\nSyllabus: ${cls.syllabus ? cls.syllabus.slice(0, 200) + (cls.syllabus.length > 200 ? \"…\" : \"\") : \"(none)\"}\n\nSECTIONS (use sectionId when creating assignments):\n${sectionList || \"  (none - suggest sectionsToCreate first)\"}\n\nMARK SCHEMES (use markSchemeId when creating assignments):\n${markSchemeList || \"  (none - suggest creating one or omit markSchemeId)\"}\n\nGRADING BOUNDARIES (use gradingBoundaryId when creating assignments):\n${gradingBoundaryList || \"  (none - suggest creating one or omit gradingBoundaryId)\"}\n\nWORKSHEETS (use worksheetIds when acceptWorksheet is true):\n${worksheetList || \"  (none - use worksheetsToCreate or create via docs first)\"}\n\nFILES - PDFs/Documents (for assignment attachments):\n${fileList || \"  (none)\"}\n\nFILES - Other (for assignment attachments):\n${otherFileList}\n\nSTUDENTS (use studentIds for specific assignment; empty array = all students):\n${studentList || \"  (none)\"}\n\nEXISTING ASSIGNMENTS (for reference, avoid duplicates):\n${assignmentSummary || \"  (none)\"}\n`.trim();\n};\n\n/**\n * @deprecated Use buildClassContextForAI for schema-aware context. Kept for compatibility.\n */\nexport const getBaseSystemPrompt = (\n  context: Class,\n  members: User[],\n  assignments: Assignment[],\n  files: File[],\n  sections: Section[]\n): string => {\n  return buildClassContextForAI({\n    class: context,\n    sections,\n    markSchemes: [],\n    gradingBoundaries: [],\n    worksheets: [],\n    files,\n    students: members,\n    teachers: [],\n    assignments,\n  });\n};\n\n\n\n/**\n * Fill the AI introduction placeholder for a brand-new lab chat.\n *\n * The caller (service layer) must have already created a PENDING AI Message\n * row — `aiMessageId` is that placeholder. This function flips it to\n * COMPLETED with the intro content, or to FAILED on a hard error.\n */\nexport const generateAndSendLabIntroduction = async (\n    labChatId: string,\n    conversationId: string,\n    _contextString: string,\n    _subject: string,\n    aiMessageId: string,\n  ): Promise<void> => {\n    const introMessage =\n      \"Hello teaching team! I'm your AI assistant for course material development. I can create worksheets, assignments, and downloadable files — PDFs, Word docs, PowerPoints, spreadsheets, and more. When you have a clear request, I'll produce it directly. I only ask questions when I need to clarify the topic or scope. What would you like to work on?\";\n\n    try {\n      await broadcastTextChunks(conversationId, aiMessageId, introMessage);\n      await completePendingAIMessage(aiMessageId, introMessage);\n      logger.info('AI Introduction sent', { labChatId, conversationId, aiMessageId });\n    } catch (error) {\n      logger.error('Failed to complete AI introduction placeholder:', {\n        error,\n        labChatId,\n        aiMessageId,\n      });\n      await failPendingAIMessage(aiMessageId, { reason: 'lab_intro_complete_failed' });\n    }\n  }\n  \n  /**\n   * Fill the AI response placeholder for a teacher reply in a lab chat.\n   *\n   * `aiMessageId` is the PENDING AI Message row created by the service\n   * layer; the pipeline flips it to COMPLETED with content / attachments /\n   * meta, or FAILED on error.  Teacher-channel `lab-response-{pending,\n   * completed,failed}` events fire alongside the chat-channel status flips\n   * (which `completePendingAIMessage` / `failPendingAIMessage` already\n   * broadcast) so the lab list \"AI busy\" indicator stays accurate.\n   *\n   * `_teacherMessage` is retained for caller compatibility — the actual\n   * conversation history is reloaded from the DB anchored on the AI\n   * placeholder.\n   */\n  export const generateAndSendLabResponse = async (\n    labChatId: string,\n    teacherMessage: string,\n    emitOptions: { classId: string; aiMessageId: string }\n  ): Promise<void> => {\n    try {\n      // Get lab context from database\n      const fullLabChat = await prisma.labChat.findUnique({\n        where: { id: labChatId },\n        include: {\n          class: {\n            select: {\n              name: true,\n              subject: true,\n            },\n          },\n        },\n      });\n  \n      if (!fullLabChat) {\n        throw new Error('Lab chat not found');\n      }\n  \n      const conversationId = fullLabChat.conversationId;\n  \n      // Anchor history on the AI placeholder — the slice will include the\n      // placeholder itself (empty content) at the top; drop it so the model\n      // does not see an empty assistant turn at the very end.\n      const anchoredMessages = await loadRecentLabChatMessages(\n        conversationId,\n        emitOptions.aiMessageId,\n      );\n      const recentMessages = anchoredMessages.filter(\n        (msg) => msg.id !== emitOptions.aiMessageId,\n      );\n  \n      const classData = await prisma.class.findUnique({\n        where: {\n          id: fullLabChat.classId,\n        },\n        include: {\n          assignments: {\n            include: {\n              section: { select: { id: true, name: true, order: true } },\n              markScheme: { select: { id: true } },\n              gradingBoundary: { select: { id: true } },\n            },\n          },\n          sections: true,\n          markSchemes: { select: { id: true, structured: true } },\n          gradingBoundaries: { select: { id: true, structured: true } },\n          worksheets: {\n            select: {\n              id: true,\n              name: true,\n              _count: { select: { questions: true } },\n            },\n          },\n          students: {\n            select: {\n              id: true,\n              username: true,\n              profile: { select: { displayName: true } },\n            },\n          },\n          teachers: {\n            select: {\n              id: true,\n              username: true,\n              profile: { select: { displayName: true } },\n            },\n          },\n          classFiles: {\n            include: {\n              files: true,\n            },\n          },\n        },\n      });\n\n      if (!classData) {\n        throw new Error('Class not found');\n      }\n\n      const classContext = buildClassContextForAI({\n        class: classData,\n        sections: classData.sections,\n        markSchemes: classData.markSchemes,\n        gradingBoundaries: classData.gradingBoundaries,\n        worksheets: classData.worksheets.map((w) => ({\n          id: w.id,\n          name: w.name,\n          questionCount: w._count.questions,\n        })),\n        files: classData.classFiles?.files ?? [],\n        students: classData.students,\n        teachers: classData.teachers,\n        assignments: classData.assignments,\n      });\n\n      // Resolve signed URLs for image attachments so the LLM can see them\n      const messagesWithAttachments = await resolveAttachmentUrls(recentMessages.reverse());\n\n      const { system, messages } = buildLabChatAgentMessages({\n        context: fullLabChat.context,\n        classContext,\n        recentMessages: messagesWithAttachments,\n        isAIUser,\n      });\n\n      // Genuine agentic generation: the model streams prose token-by-token and\n      // calls real tools inline — read-only RAG lookups plus \"propose_*\" tools\n      // that record create-actions into `proposals`. `streamChatResponse`\n      // broadcasts the real text chunks and tool-call events as they happen.\n      const proposals = createLabProposals();\n      const tools = {\n        ...aiTools(fullLabChat.classId),\n        ...labProposalTools(proposals),\n      };\n\n      const { text: streamedText, parts: rawStreamParts } = await withTimeout(\n        streamChatResponse({\n          conversationId,\n          aiMessageId: emitOptions.aiMessageId,\n          system,\n          messages,\n          tools,\n          temperature: 0.7,\n          maxOutputTokens: 4096,\n          maxSteps: 8,\n        }),\n        LAB_CHAT_RESPONSE_TIMEOUT_MS,\n        \"Lab chat response generation\",\n      );\n\n      // Real text + tool-call events were already broadcast inline (in order)\n      // during the stream by `streamChatResponse`. Just close the stream.\n      await broadcastStreamComplete(conversationId, emitOptions.aiMessageId);\n\n      // `generate_document` is an inline tool that only QUEUES into `proposals.docs`\n      // during the stream. OpenAI Code Interpreter renders files here, after the\n      // stream ends, then we link them to this message.\n      try {\n        const attachmentIds: string[] = [];\n        const generatedDocFiles: GeneratedDocFileLink[] = [];\n        const resolvedDocs: Array<{ title: string; format: string }> = [];\n\n        for (const doc of proposals.docs) {\n          if (!doc.title || !doc.content?.trim()) {\n            logger.error('Document missing title or content', { labChatId, doc });\n            continue;\n          }\n\n          const format = inferDocumentFormat(\n            doc.title,\n            doc.content,\n            doc.format,\n            teacherMessage,\n          );\n          resolvedDocs.push({ title: doc.title, format });\n\n          if (format !== normalizeDocumentFormat(doc.format)) {\n            logger.info('Document format overridden from model default', {\n              labChatId,\n              title: doc.title,\n              modelFormat: doc.format,\n              resolvedFormat: format,\n            });\n          }\n\n          try {\n            const generated = await generateDocumentWithOpenAI({\n              title: doc.title,\n              content: doc.content,\n              format,\n            });\n            if (!generated) {\n              logger.error('OpenAI document generation returned null', {\n                labChatId,\n                title: doc.title,\n                format: doc.format,\n              });\n              continue;\n            }\n\n            const sanitizedTitle = doc.title\n              .replace(/[^a-zA-Z0-9\\s\\-_]/g, '')\n              .replace(/\\s+/g, '_')\n              .substring(0, 50);\n            const filename = `${sanitizedTitle}_${v4().substring(0, 8)}.${generated.format}`;\n            const filePath = `class/generated/${fullLabChat.classId}/${filename}`;\n\n            await bucket.file(filePath).save(generated.bytes, {\n              metadata: { contentType: generated.mimeType },\n            });\n\n            const file = await prisma.file.create({\n              data: {\n                name: filename,\n                path: filePath,\n                type: generated.mimeType,\n                size: generated.bytes.length,\n                userId: fullLabChat.createdById,\n                conversationId,\n                messageId: emitOptions.aiMessageId,\n                uploadStatus: 'COMPLETED',\n                uploadedAt: new Date(),\n              },\n            });\n\n            attachmentIds.push(file.id);\n            generatedDocFiles.push({\n              title: doc.title,\n              fileId: file.id,\n              fileName: filename,\n              format: generated.format,\n            });\n          } catch (docError) {\n            logger.error('Document generation failed', {\n              error: docError instanceof Error ? {\n                message: docError.message,\n                stack: docError.stack,\n                name: docError.name,\n              } : docError,\n              labChatId,\n              title: doc.title,\n              format: doc.format,\n            });\n          }\n        }\n        \n        const streamParts: StreamPart[] = enrichStreamPartsWithGeneratedFiles(\n          applyResolvedFormatsToStreamParts(rawStreamParts, resolvedDocs),\n          generatedDocFiles,\n        );\n\n        for (const part of streamParts) {\n          if (\n            part.type === 'tool' &&\n            part.toolName === 'generate_document' &&\n            part.fileId\n          ) {\n            await pusher\n              .trigger(chatChannel(conversationId), 'message-tool-call', {\n                messageId: emitOptions.aiMessageId,\n                toolCallId: part.toolCallId,\n                toolName: part.toolName,\n                ...(part.title ? { title: part.title } : {}),\n                ...(part.format ? { format: part.format } : {}),\n                fileId: part.fileId,\n                fileName: part.fileName,\n                status: 'completed',\n              })\n              .catch(() => {});\n          }\n        }\n\n        await completePendingAIMessage(emitOptions.aiMessageId, streamedText, {\n          ...(attachmentIds.length > 0 && {\n            attachments: { connect: attachmentIds.map((id) => ({ id })) },\n          }),\n          meta: {\n            assignmentsToCreate: proposals.assignments.length > 0\n              ? proposals.assignments.map(assignment => ({ ...assignment, id: v4() }))\n              : null,\n            worksheetsToCreate: proposals.worksheets.length > 0\n              ? proposals.worksheets.map(worksheet => ({ ...worksheet, id: v4() }))\n              : null,\n            sectionsToCreate: proposals.sections.length > 0\n              ? proposals.sections.map(section => ({ ...section, id: v4() }))\n              : null,\n            streamParts: streamParts.length > 0 ? streamParts : null,\n          },\n        });\n      } catch (persistError) {\n        logger.error('Failed to persist AI response or generate PDF:', { error: persistError, labChatId });\n        // Fallback: complete the placeholder with the raw text so the\n        // teacher still sees something useful instead of FAILED.\n        await completePendingAIMessage(emitOptions.aiMessageId, streamedText);\n      }\n\n      try {\n        await pusher.trigger(teacherChannel(emitOptions.classId), \"lab-response-completed\", {\n          labChatId,\n          messageId: emitOptions.aiMessageId,\n        });\n      } catch (broadcastError) {\n        logger.error(\"Failed to broadcast lab response completed:\", { error: broadcastError });\n      }\n\n      logger.info('AI response sent', { labChatId, conversationId, aiMessageId: emitOptions.aiMessageId });\n\n    } catch (error) {\n      console.error('Full error object:', error);\n      logger.error('Failed to generate AI response:', {\n        error: error instanceof Error ? {\n          message: error.message,\n          stack: error.stack,\n          name: error.name\n        } : error,\n        labChatId,\n        aiMessageId: emitOptions.aiMessageId,\n      });\n\n      await failPendingAIMessage(emitOptions.aiMessageId, {\n        reason: 'lab_response_generation_failed',\n      });\n\n      try {\n        await pusher.trigger(teacherChannel(emitOptions.classId), \"lab-response-failed\", {\n          labChatId,\n          messageId: emitOptions.aiMessageId,\n          error: \"AI response generation failed\",\n        });\n      } catch (broadcastError) {\n        logger.error(\"Failed to broadcast lab response failed:\", { error: broadcastError });\n      }\n\n      throw error; // Re-throw to see the full error in the calling function\n    }\n  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