@studious-lms/server 1.4.9 → 1.6.0

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

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package/dist/pipelines/aiLabChat.js

@@ -3,12 +3,11 @@
  * Can create worksheets, sections, assignments, and PDF docs 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]="0181f16e-08db-56bd-b00d-d970d94af9d3")}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]="e57f7401-27fd-5eac-a76a-cb84f699b776")}catch(e){}}();
 import { isAIUser } from "../utils/aiUser.js";
 import { prisma } from "../lib/prisma.js";
-import { GenerationStatus } from "@prisma/client";
 import { pusher, teacherChannel } from "../lib/pusher.js";
-import { inference, sendAIMessage } from "../utils/inference.js";
+import { inference, completePendingAIMessage, failPendingAIMessage, } from "../utils/inference.js";
 import { logger } from "../utils/logger.js";
 import { createPdf } from "../lib/jsonConversion.js";
 import { v4 } from "uuid";
@@ -239,7 +238,7 @@ export const getBaseSystemPrompt = (context, members, assignments, files, sectio
 //             content: "GENERATING_CONTENT",
 //             senderId: getAIUserId(),
 //             conversationId: labChatId,
-//             status: GenerationStatus.PENDING,   
+//             status: JobStatus.PENDING,
 //         },
 //     });
 //     try {
@@ -248,35 +247,40 @@ export const getBaseSystemPrompt = (context, members, assignments, files, sectio
 //     }
 // };
 /**
- * Generate and send AI introduction for lab chat
- * Uses the stored context directly from database
+ * Fill the AI introduction placeholder for a brand-new lab chat.
+ *
+ * The caller (service layer) must have already created a PENDING AI Message
+ * row — `aiMessageId` is that placeholder. This function flips it to
+ * COMPLETED with the intro content, or to FAILED on a hard error.
  */
-export const generateAndSendLabIntroduction = async (labChatId, conversationId, _contextString, subject) => {
+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?";
     try {
-        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?";
-        await sendAIMessage(introMessage, conversationId, { subject });
-        logger.info('AI Introduction sent', { labChatId, conversationId });
+        await completePendingAIMessage(aiMessageId, introMessage);
+        logger.info('AI Introduction sent', { labChatId, conversationId, aiMessageId });
     }
     catch (error) {
-        logger.error('Failed to generate AI introduction:', { error, labChatId });
-        // Send fallback introduction
-        try {
-            const fallbackIntro = `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?`;
-            await sendAIMessage(fallbackIntro, conversationId, {
-                subject,
-            });
-            logger.info('Fallback AI introduction sent', { labChatId });
-        }
-        catch (fallbackError) {
-            logger.error('Failed to send fallback AI introduction:', { error: fallbackError, labChatId });
-        }
+        logger.error('Failed to complete AI introduction placeholder:', {
+            error,
+            labChatId,
+            aiMessageId,
+        });
+        await failPendingAIMessage(aiMessageId, { reason: 'lab_intro_complete_failed' });
     }
 };
 /**
- * Generate and send AI response to teacher message
- * Uses the stored context directly from database
- * @param emitOptions - When provided, emits lab-response-completed/failed on teacher channel
- * `_teacherMessage` is retained for caller compatibility while generation is anchored by `emitOptions.messageId`.
+ * Fill the AI response placeholder for a teacher reply in a lab chat.
+ *
+ * `aiMessageId` is the PENDING AI Message row created by the service
+ * layer; the pipeline flips it to COMPLETED with content / attachments /
+ * meta, or FAILED on error.  Teacher-channel `lab-response-{pending,
+ * completed,failed}` events fire alongside the chat-channel status flips
+ * (which `completePendingAIMessage` / `failPendingAIMessage` already
+ * broadcast) so the lab list "AI busy" indicator stays accurate.
+ *
+ * `_teacherMessage` is retained for caller compatibility — the actual
+ * conversation history is reloaded from the DB anchored on the AI
+ * placeholder.
  */
 export const generateAndSendLabResponse = async (labChatId, _teacherMessage, emitOptions) => {
     try {
@@ -296,7 +300,11 @@ export const generateAndSendLabResponse = async (labChatId, _teacherMessage, emi
             throw new Error('Lab chat not found');
         }
         const conversationId = fullLabChat.conversationId;
-        const recentMessages = await loadRecentLabChatMessages(conversationId, emitOptions?.messageId);
+        // Anchor history on the AI placeholder — the slice will include the
+        // placeholder itself (empty content) at the top; drop it so the model
+        // does not see an empty assistant turn at the very end.
+        const anchoredMessages = await loadRecentLabChatMessages(conversationId, emitOptions.aiMessageId);
+        const recentMessages = anchoredMessages.filter((msg) => msg.id !== emitOptions.aiMessageId);
         const classData = await prisma.class.findUnique({
             where: {
                 id: fullLabChat.classId,
@@ -376,7 +384,7 @@ export const generateAndSendLabResponse = async (labChatId, _teacherMessage, emi
                 labChatId,
                 conversationId,
                 classId: fullLabChat.classId,
-                ...(emitOptions?.messageId ? { messageId: emitOptions.messageId } : {}),
+                aiMessageId: emitOptions.aiMessageId,
             },
         }), LAB_CHAT_RESPONSE_TIMEOUT_MS, "Lab chat response generation");
         if (!response) {
@@ -443,8 +451,7 @@ export const generateAndSendLabResponse = async (labChatId, _teacherMessage, emi
                     }
                 }
             }
-            // Send the text response to the conversation
-            await sendAIMessage(jsonData.text, conversationId, {
+            await completePendingAIMessage(emitOptions.aiMessageId, jsonData.text, {
                 attachments: {
                     connect: attachmentIds.map(id => ({ id })),
                 },
@@ -462,32 +469,24 @@ export const generateAndSendLabResponse = async (labChatId, _teacherMessage, emi
                         id: v4(),
                     })) || null,
                 },
-                subject: fullLabChat.class?.subject || 'Lab',
             });
         }
         catch (parseError) {
             logger.error('Failed to parse AI response or generate PDF:', { error: parseError, labChatId });
-            // Fallback: send the raw response if parsing fails
-            await sendAIMessage(response.text, conversationId, {
-                subject: fullLabChat.class?.subject || 'Lab',
-            });
+            // Fallback: complete the placeholder with the raw text so the
+            // teacher still sees something useful instead of FAILED.
+            await completePendingAIMessage(emitOptions.aiMessageId, response.text);
         }
-        if (emitOptions) {
-            await prisma.message.update({
-                where: { id: emitOptions.messageId },
-                data: { status: GenerationStatus.COMPLETED },
+        try {
+            await pusher.trigger(teacherChannel(emitOptions.classId), "lab-response-completed", {
+                labChatId,
+                messageId: emitOptions.aiMessageId,
             });
-            try {
-                await pusher.trigger(teacherChannel(emitOptions.classId), "lab-response-completed", {
-                    labChatId,
-                    messageId: emitOptions.messageId,
-                });
-            }
-            catch (broadcastError) {
-                logger.error("Failed to broadcast lab response completed:", { error: broadcastError });
-            }
         }
-        logger.info('AI response sent', { labChatId, conversationId });
+        catch (broadcastError) {
+            logger.error("Failed to broadcast lab response completed:", { error: broadcastError });
+        }
+        logger.info('AI response sent', { labChatId, conversationId, aiMessageId: emitOptions.aiMessageId });
     }
     catch (error) {
         console.error('Full error object:', error);
@@ -497,35 +496,24 @@ export const generateAndSendLabResponse = async (labChatId, _teacherMessage, emi
                 stack: error.stack,
                 name: error.name
             } : error,
-            labChatId
+            labChatId,
+            aiMessageId: emitOptions.aiMessageId,
         });
-        if (emitOptions) {
-            try {
-                await prisma.message.update({
-                    where: { id: emitOptions.messageId },
-                    data: { status: GenerationStatus.FAILED },
-                });
-            }
-            catch (statusError) {
-                logger.error("Failed to set message status FAILED:", {
-                    error: statusError,
-                    labChatId,
-                    messageId: emitOptions.messageId,
-                });
-            }
-            try {
-                await pusher.trigger(teacherChannel(emitOptions.classId), "lab-response-failed", {
-                    labChatId,
-                    messageId: emitOptions.messageId,
-                    error: "AI response generation failed",
-                });
-            }
-            catch (broadcastError) {
-                logger.error("Failed to broadcast lab response failed:", { error: broadcastError });
-            }
+        await failPendingAIMessage(emitOptions.aiMessageId, {
+            reason: 'lab_response_generation_failed',
+        });
+        try {
+            await pusher.trigger(teacherChannel(emitOptions.classId), "lab-response-failed", {
+                labChatId,
+                messageId: emitOptions.aiMessageId,
+                error: "AI response generation failed",
+            });
+        }
+        catch (broadcastError) {
+            logger.error("Failed to broadcast lab response failed:", { error: broadcastError });
         }
         throw error; // Re-throw to see the full error in the calling function
     }
 };
 //# sourceMappingURL=aiLabChat.js.map
-//# debugId=0181f16e-08db-56bd-b00d-d970d94af9d3
+//# debugId=e57f7401-27fd-5eac-a76a-cb84f699b776

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 { GenerationStatus } from \"@prisma/client\";\nimport { pusher, teacherChannel } from \"../lib/pusher.js\";\nimport type { Assignment, Class, File, Section, User } from \"@prisma/client\";\nimport { inference, sendAIMessage } 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 { type LabChatResponse, labChatResponseSchema } from \"./aiLabChatContract.js\";\nimport { buildLabChatResponseMessages } from \"./labChatPrompt.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 * Generate labchat responses\n * Allow for the generation of the following:\n * - Assignment(s) either individual or bulk as an lesson / course plan.\n * - Worksheet(s) either individual or bulk as an lesson / course plan.\n * - Files (PDFs)\n * @param labChatId \n */\n// export const sendAiLabChatResponsePipeline = async (labChatId: string) => {\n//     const message = await prisma?.message.create({\n//         data: {\n//             content: \"GENERATING_CONTENT\",\n//             senderId: getAIUserId(),\n//             conversationId: labChatId,\n//             status: GenerationStatus.PENDING,   \n//         },\n//     });\n\n//     try {\n\n//         inference(`\n//         `)\n//     }\n    \n// };\n\n\n/**\n * Generate and send AI introduction for lab chat\n * Uses the stored context directly from database\n */\nexport const generateAndSendLabIntroduction = async (\n    labChatId: string,\n    conversationId: string,\n    _contextString: string,\n    subject: string\n  ): Promise<void> => {\n    try {\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      await sendAIMessage(introMessage, conversationId, { subject });\n  \n      logger.info('AI Introduction sent', { labChatId, conversationId });\n  \n    } catch (error) {\n      logger.error('Failed to generate AI introduction:', { error, labChatId });\n      \n      // Send fallback introduction\n      try {\n        const fallbackIntro = `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        await sendAIMessage(fallbackIntro, conversationId, {\n          subject,\n        });\n  \n        logger.info('Fallback AI introduction sent', { labChatId });\n  \n      } catch (fallbackError) {\n        logger.error('Failed to send fallback AI introduction:', { error: fallbackError, labChatId });\n      }\n    }\n  }\n  \n  /**\n   * Generate and send AI response to teacher message\n   * Uses the stored context directly from database\n   * @param emitOptions - When provided, emits lab-response-completed/failed on teacher channel\n   * `_teacherMessage` is retained for caller compatibility while generation is anchored by `emitOptions.messageId`.\n   */\n  export const generateAndSendLabResponse = async (\n    labChatId: string,\n    _teacherMessage: string,\n    emitOptions?: { classId: string; messageId: 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      const recentMessages = await loadRecentLabChatMessages(\n        conversationId,\n        emitOptions?.messageId,\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 messages = buildLabChatResponseMessages({\n        context: fullLabChat.context,\n        classContext,\n        recentMessages: recentMessages.reverse(),\n        isAIUser,\n      });\n  \n  \n    //   const completion = await inferenceClient.chat.completions.create({\n    //     model: 'command-a-03-2025',\n    //     messages,\n    //     temperature: 0.7,\n    //     response_format: zodTextFormat(labChatResponseSchema, \"lab_chat_response_format\"),\n    //   });\n\n    const response = await withTimeout(\n      inference<LabChatResponse>(messages, labChatResponseSchema, {\n        reason: 'lab_chat_response',\n        metadata: {\n          labChatId,\n          conversationId,\n          classId: fullLabChat.classId,\n          ...(emitOptions?.messageId ? { messageId: emitOptions.messageId } : {}),\n        },\n      }),\n      LAB_CHAT_RESPONSE_TIMEOUT_MS,\n      \"Lab chat response generation\",\n    );\n        \n      if (!response) {\n        throw new Error('No response generated from inference API');\n      }\n      // Parse the JSON response and generate PDF if docs are provided\n      try {\n        const jsonData = response;\n  \n  \n        const attachmentIds: string[] = [];\n        // Generate PDFs if docs are provided\n        if (jsonData.docs && Array.isArray(jsonData.docs)) {\n          \n  \n          for (let i = 0; i < jsonData.docs.length; i++) {\n            const doc = jsonData.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        // Send the text response to the conversation\n        await sendAIMessage(jsonData.text, conversationId, {\n          attachments: {\n            connect: attachmentIds.map(id => ({ id })),\n          },\n          meta: {\n            assignmentsToCreate: jsonData.assignmentsToCreate?.map(assignment => ({\n              ...assignment,\n              id: v4(),\n            })) || null,\n            worksheetsToCreate: jsonData.worksheetsToCreate?.map(worksheet => ({\n              ...worksheet,\n              id: v4(),\n            })) || null,\n            sectionsToCreate: jsonData.sectionsToCreate?.map(section => ({\n              ...section,\n              id: v4(),\n            })) || null,\n          },\n          subject: fullLabChat.class?.subject || 'Lab',\n        });\n      } catch (parseError) {\n        logger.error('Failed to parse AI response or generate PDF:', { error: parseError, labChatId });\n        // Fallback: send the raw response if parsing fails\n        await sendAIMessage(response.text, conversationId, {\n          subject: fullLabChat.class?.subject || 'Lab',\n        });\n      }\n\n      if (emitOptions) {\n        await prisma.message.update({\n          where: { id: emitOptions.messageId },\n          data: { status: GenerationStatus.COMPLETED },\n        });\n        try {\n          await pusher.trigger(teacherChannel(emitOptions.classId), \"lab-response-completed\", {\n            labChatId,\n            messageId: emitOptions.messageId,\n          });\n        } catch (broadcastError) {\n          logger.error(\"Failed to broadcast lab response completed:\", { error: broadcastError });\n        }\n      }\n\n      logger.info('AI response sent', { labChatId, conversationId });\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      });\n\n      if (emitOptions) {\n        try {\n          await prisma.message.update({\n            where: { id: emitOptions.messageId },\n            data: { status: GenerationStatus.FAILED },\n          });\n        } catch (statusError) {\n          logger.error(\"Failed to set message status FAILED:\", {\n            error: statusError,\n            labChatId,\n            messageId: emitOptions.messageId,\n          });\n        }\n        try {\n          await pusher.trigger(teacherChannel(emitOptions.classId), \"lab-response-failed\", {\n            labChatId,\n            messageId: emitOptions.messageId,\n            error: \"AI response generation failed\",\n          });\n        } catch (broadcastError) {\n          logger.error(\"Failed to broadcast lab response failed:\", { error: broadcastError });\n        }\n      }\n\n      throw error; // Re-throw to see the full error in the calling function\n    }\n  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from \"./labChatPrompt.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 * Generate labchat responses\n * Allow for the generation of the following:\n * - Assignment(s) either individual or bulk as an lesson / course plan.\n * - Worksheet(s) either individual or bulk as an lesson / course plan.\n * - Files (PDFs)\n * @param labChatId \n */\n// export const sendAiLabChatResponsePipeline = async (labChatId: string) => {\n//     const message = await prisma?.message.create({\n//         data: {\n//             content: \"GENERATING_CONTENT\",\n//             senderId: getAIUserId(),\n//             conversationId: labChatId,\n//             status: JobStatus.PENDING,\n//         },\n//     });\n\n//     try {\n\n//         inference(`\n//         `)\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 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 messages = buildLabChatResponseMessages({\n        context: fullLabChat.context,\n        classContext,\n        recentMessages: recentMessages.reverse(),\n        isAIUser,\n      });\n  \n  \n    //   const completion = await inferenceClient.chat.completions.create({\n    //     model: 'command-a-03-2025',\n    //     messages,\n    //     temperature: 0.7,\n    //     response_format: zodTextFormat(labChatResponseSchema, \"lab_chat_response_format\"),\n    //   });\n\n    const response = await withTimeout(\n      inference<LabChatResponse>(messages, labChatResponseSchema, {\n        reason: 'lab_chat_response',\n        metadata: {\n          labChatId,\n          conversationId,\n          classId: fullLabChat.classId,\n          aiMessageId: emitOptions.aiMessageId,\n        },\n      }),\n      LAB_CHAT_RESPONSE_TIMEOUT_MS,\n      \"Lab chat response generation\",\n    );\n        \n      if (!response) {\n        throw new Error('No response generated from inference API');\n      }\n      // Parse the JSON response and generate PDF if docs are provided\n      try {\n        const jsonData = response;\n  \n  \n        const attachmentIds: string[] = [];\n        // Generate PDFs if docs are provided\n        if (jsonData.docs && Array.isArray(jsonData.docs)) {\n          \n  \n          for (let i = 0; i < jsonData.docs.length; i++) {\n            const doc = jsonData.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, jsonData.text, {\n          attachments: {\n            connect: attachmentIds.map(id => ({ id })),\n          },\n          meta: {\n            assignmentsToCreate: jsonData.assignmentsToCreate?.map(assignment => ({\n              ...assignment,\n              id: v4(),\n            })) || null,\n            worksheetsToCreate: jsonData.worksheetsToCreate?.map(worksheet => ({\n              ...worksheet,\n              id: v4(),\n            })) || null,\n            sectionsToCreate: jsonData.sectionsToCreate?.map(section => ({\n              ...section,\n              id: v4(),\n            })) || null,\n          },\n        });\n      } catch (parseError) {\n        logger.error('Failed to parse AI response or generate PDF:', { error: parseError, 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, response.text);\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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package/dist/pipelines/aiNewtonChat.d.ts

@@ -10,11 +10,20 @@ export interface AIPolicyLevel {
 }
 export declare const AI_POLICY_LEVELS: AIPolicyLevel[];
 /**
- * Generate and send AI introduction for Newton chat
+ * Fill the Newton tutor introduction placeholder.
+ *
+ * `aiMessageId` is the PENDING AI Message row created by the service layer
+ * (see `getTutorConversation`). On success we flip it to COMPLETED with the
+ * generated intro; on failure we fall back to a hardcoded greeting before
+ * marking the placeholder FAILED only as a last resort.
  */
-export declare const generateAndSendNewtonIntroduction: (newtonChatId: string, conversationId: string, submissionId: string) => Promise<void>;
+export declare const generateAndSendNewtonIntroduction: (newtonChatId: string, conversationId: string, submissionId: string, aiMessageId: string) => Promise<void>;
 /**
- * Generate and send AI response to student message
+ * Fill the Newton AI response placeholder for a student turn.
+ *
+ * `aiMessageId` is the PENDING AI Message row the service created post-tx;
+ * the pipeline flips it to COMPLETED with the generated content (the
+ * helper broadcasts `message-updated` on the chat channel) or to FAILED.
  */
 export declare const generateAndSendNewtonResponse: (newtonChatId: string, studentMessage: string, conversationId: string, submission: {
     id: string;
@@ -26,5 +35,5 @@ export declare const generateAndSendNewtonResponse: (newtonChatId: string, stude
             subject: string | null;
         };
     };
-}) => Promise<void>;
+}, aiMessageId: string) => Promise<void>;
 //# sourceMappingURL=aiNewtonChat.d.ts.map

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

@@ -1 +1 @@
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+{"version":3,"file":"aiNewtonChat.d.ts","sourceRoot":"/","sources":["pipelines/aiNewtonChat.ts"],"names":[],"mappings":"AAiBA,MAAM,WAAW,aAAa;IAC1B,KAAK,EAAE,MAAM,CAAC;IACd,QAAQ,EAAE,MAAM,CAAC;IACjB,cAAc,EAAE,MAAM,CAAC;IACvB,WAAW,EAAE,MAAM,CAAC;IACpB,0BAA0B,EAAE,MAAM,CAAC;IACnC,yBAAyB,EAAE,MAAM,CAAC;IAClC,KAAK,EAAE,MAAM,CAAC;IACd,QAAQ,EAAE,MAAM,CAAC;CAClB;AAGD,eAAO,MAAM,gBAAgB,EAAE,aAAa,EAmD3C,CAAC;AAEJ;;;;;;;GAOG;AACH,eAAO,MAAM,iCAAiC,GAC1C,cAAc,MAAM,EACpB,gBAAgB,MAAM,EACtB,cAAc,MAAM,EACpB,aAAa,MAAM,KAClB,OAAO,CAAC,IAAI,CAwFd,CAAA;AA8BD;;;;;;GAMG;AACH,eAAO,MAAM,6BAA6B,GACxC,cAAc,MAAM,EACpB,gBAAgB,MAAM,EACtB,gBAAgB,MAAM,EACtB,YAAY;IACV,EAAE,EAAE,MAAM,CAAC;IACX,UAAU,EAAE;QACV,EAAE,EAAE,MAAM,CAAC;QACX,KAAK,EAAE,MAAM,CAAC;QACd,YAAY,EAAE,MAAM,GAAG,IAAI,CAAC;QAC5B,KAAK,EAAE;YACL,OAAO,EAAE,MAAM,GAAG,IAAI,CAAC;SACxB,CAAC;KACH,CAAC;CACH,EACD,aAAa,MAAM,KAClB,OAAO,CAAC,IAAI,CAuId,CAAA"}

package/dist/pipelines/aiNewtonChat.js

@@ -3,11 +3,10 @@
  * Uses assignment context and AI policy levels for tutoring.
  */
 
-!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]="f0e147dd-0983-54a0-a589-255ca9d22381")}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]="0235905e-5a7d-5489-8f86-d2f18c7fffb2")}catch(e){}}();
 import { prisma } from "../lib/prisma.js";
-import { inference } from "../utils/inference.js";
+import { inference, completePendingAIMessage, failPendingAIMessage, } from "../utils/inference.js";
 import { logger } from "../utils/logger.js";
-import { sendAIMessage } from "../utils/inference.js";
 import { isAIUser } from "../utils/aiUser.js";
 // AI Policy levels configuration with translation keys
 export const AI_POLICY_LEVELS = [
@@ -63,9 +62,14 @@ export const AI_POLICY_LEVELS = [
     }
 ];
 /**
- * Generate and send AI introduction for Newton chat
+ * Fill the Newton tutor introduction placeholder.
+ *
+ * `aiMessageId` is the PENDING AI Message row created by the service layer
+ * (see `getTutorConversation`). On success we flip it to COMPLETED with the
+ * generated intro; on failure we fall back to a hardcoded greeting before
+ * marking the placeholder FAILED only as a last resort.
  */
-export const generateAndSendNewtonIntroduction = async (newtonChatId, conversationId, submissionId) => {
+export const generateAndSendNewtonIntroduction = async (newtonChatId, conversationId, submissionId, aiMessageId) => {
     try {
         // Get submission details for context
         const submission = await prisma.submission.findUnique({
@@ -121,6 +125,7 @@ export const generateAndSendNewtonIntroduction = async (newtonChatId, conversati
                 newtonChatId,
                 conversationId,
                 submissionId: submission.id,
+                aiMessageId,
             },
             model: 'command-a-03-2025',
             maxTokens: 300,
@@ -129,24 +134,21 @@ export const generateAndSendNewtonIntroduction = async (newtonChatId, conversati
         if (!response) {
             throw new Error('No response generated from inference API');
         }
-        // Send AI introduction using centralized sender
-        await sendAIMessage(response, conversationId, {
-            subject: submission.assignment.class.subject || 'Assignment',
-        });
-        logger.info('AI Introduction sent', { newtonChatId, conversationId });
+        await completePendingAIMessage(aiMessageId, response);
+        logger.info('AI Introduction sent', { newtonChatId, conversationId, aiMessageId });
     }
     catch (error) {
-        logger.error('Failed to generate AI introduction:', { error, newtonChatId });
-        // Send fallback introduction
+        logger.error('Failed to generate AI introduction:', { error, newtonChatId, aiMessageId });
+        // Fallback: still complete the placeholder so the student isn't stuck
+        // staring at an empty bubble.
         try {
             const fallbackIntro = `Hello! I'm Newton, your AI tutor. I'm here to help you with your assignment. I can answer questions, explain concepts, and guide you through your work. What would you like help with today?`;
-            await sendAIMessage(fallbackIntro, conversationId, {
-                subject: 'Assignment',
-            });
-            logger.info('Fallback AI introduction sent', { newtonChatId });
+            await completePendingAIMessage(aiMessageId, fallbackIntro);
+            logger.info('Fallback AI introduction sent', { newtonChatId, aiMessageId });
         }
         catch (fallbackError) {
-            logger.error('Failed to send fallback AI introduction:', { error: fallbackError, newtonChatId });
+            logger.error('Failed to send fallback AI introduction:', { error: fallbackError, newtonChatId, aiMessageId });
+            await failPendingAIMessage(aiMessageId, { reason: 'newton_intro_fallback_failed' });
         }
     }
 };
@@ -178,14 +180,21 @@ const formatAssignmentString = (assignment) => {
   `;
 };
 /**
- * Generate and send AI response to student message
+ * Fill the Newton AI response placeholder for a student turn.
+ *
+ * `aiMessageId` is the PENDING AI Message row the service created post-tx;
+ * the pipeline flips it to COMPLETED with the generated content (the
+ * helper broadcasts `message-updated` on the chat channel) or to FAILED.
  */
-export const generateAndSendNewtonResponse = async (newtonChatId, studentMessage, conversationId, submission) => {
+export const generateAndSendNewtonResponse = async (newtonChatId, studentMessage, conversationId, submission, aiMessageId) => {
     try {
-        // Get recent conversation history
+        // Get recent conversation history (excluding the empty AI placeholder
+        // we just created — otherwise the model sees a blank assistant turn at
+        // the very end of the transcript).
         const recentMessages = await prisma.message.findMany({
             where: {
                 conversationId,
+                id: { not: aiMessageId },
             },
             include: {
                 sender: {
@@ -274,16 +283,14 @@ export const generateAndSendNewtonResponse = async (newtonChatId, studentMessage
                 newtonChatId,
                 conversationId,
                 submissionId: submission.id,
+                aiMessageId,
             },
         });
         if (!response) {
             throw new Error('No response generated from inference API');
         }
-        // Send the text response to the conversation
-        await sendAIMessage(response, conversationId, {
-            subject: submission.assignment.class.subject || 'Assignment',
-        });
-        logger.info('AI response sent', { newtonChatId, conversationId });
+        await completePendingAIMessage(aiMessageId, response);
+        logger.info('AI response sent', { newtonChatId, conversationId, aiMessageId });
     }
     catch (error) {
         logger.error('Failed to generate AI response:', {
@@ -292,9 +299,14 @@ export const generateAndSendNewtonResponse = async (newtonChatId, studentMessage
                 stack: error.stack,
                 name: error.name
             } : error,
-            newtonChatId
+            newtonChatId,
+            aiMessageId,
+        });
+        await failPendingAIMessage(aiMessageId, {
+            reason: 'newton_response_generation_failed',
         });
+        throw error;
     }
 };
 //# sourceMappingURL=aiNewtonChat.js.map
-//# debugId=f0e147dd-0983-54a0-a589-255ca9d22381
+//# debugId=0235905e-5a7d-5489-8f86-d2f18c7fffb2