@studious-lms/server 1.25.0 → 1.27.0

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 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 } from \"../lib/googleCloudStorage.js\";\nimport {\n  generateDocumentWithOpenAI,\n  normalizeDocumentFormat,\n} from \"../services/openaiDocumentGen.js\";\nimport { inferDocumentFormat } from \"../lib/inferDocumentFormat.js\";\nimport { broadcastTextChunks, broadcastStreamComplete } from \"../utils/streamBroadcast.js\";\nimport { AI_CHAT_MODEL } from \"../lib/chatAttachmentPrompt.js\";\nimport { buildLabChatAgentMessages } from \"./labChatPrompt.js\";\nimport {\n  applyResolvedFormatsToStreamParts,\n  enrichStreamPartsWithGeneratedFiles,\n  finalizeDeferredToolParts,\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 * 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; userId?: string | null }\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 } = await 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: rawStreamParts } = await withTimeout(\n        streamChatResponse({\n          conversationId,\n          aiMessageId: emitOptions.aiMessageId,\n          model: AI_CHAT_MODEL,\n          system,\n          messages,\n          usageReason: 'lab_chat_response',\n          attribution: {\n            userId: emitOptions.userId ?? fullLabChat.createdById,\n            classId: emitOptions.classId,\n          },\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 (let i = 0; i < proposals.docs.length; i++) {\n          const doc = proposals.docs[i];\n          if (!doc.title || !doc.content?.trim()) {\n            logger.error(`Document ${i + 1} is 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(`Document ${i + 1} generation returned null`, {\n                labChatId,\n                title: doc.title,\n                format,\n              });\n              continue;\n            }\n\n            const sanitizedTitle = doc.title\n              .replace(/[^a-zA-Z0-9\\s\\-_]/g, '')\n              .replace(/\\s+/g, '_')\n              .substring(0, 50);\n            const filename = `${sanitizedTitle}_${v4().substring(0, 8)}.${generated.format}`;\n            const filePath = `class/generated/${fullLabChat.classId}/${filename}`;\n\n            logger.info(`Document ${i + 1} generated successfully`, {\n              labChatId,\n              title: doc.title,\n              format: generated.format,\n            });\n\n            await bucket.file(filePath).save(generated.bytes, {\n              metadata: { contentType: generated.mimeType },\n            });\n\n            logger.info(`Document ${i + 1} uploaded successfully`, { labChatId, filename });\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 for item ${i + 1}:`, {\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[] = finalizeDeferredToolParts(\n          enrichStreamPartsWithGeneratedFiles(\n            applyResolvedFormatsToStreamParts(rawStreamParts, resolvedDocs),\n            generatedDocFiles,\n          ),\n        );\n\n        // While the message is still PENDING, resolve deferred tool indicators\n        // (spinner → attachment or error) before the final persist event.\n        for (const part of streamParts) {\n          if (part.type !== 'tool' || part.toolName !== 'generate_document') {\n            continue;\n          }\n          if (part.status === 'executing') continue;\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              ...(part.fileId ? { fileId: part.fileId, fileName: part.fileName } : {}),\n              status: part.status,\n            })\n            .catch(() => {});\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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broadcastTextChunks, broadcastStreamComplete } from \"../utils/streamBroadcast.js\";\nimport { AI_CHAT_MODEL } from \"../lib/chatAttachmentPrompt.js\";\nimport { buildLabChatAgentMessages } from \"./labChatPrompt.js\";\nimport {\n  applyResolvedFormatsToStreamParts,\n  enrichStreamPartsWithGeneratedFiles,\n  finalizeDeferredToolParts,\n  streamChatResponse,\n  type GeneratedDocFileLink,\n  type StreamPart,\n} from \"../services/aiChatStream.js\";\nimport { aiTools } from \"../services/aiTools.js\";\nimport {\n  findOrCreateChildFolderByName,\n  findOrCreateScopeRoot,\n} from \"../models/cloudStorage.js\";\nimport { labProposalTools, createLabProposals } from \"../services/aiProposalTools.js\";\nimport { buildPendingCreations } from \"../services/aiProposals.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\n/** Class-files folder that collects AI-generated documents (created lazily). */\nexport const AI_GENERATED_FOLDER_NAME = \"AI Generated\";\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 * 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 - propose a section 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${worksheetList || \"  (none - propose a worksheet or create via docs first)\"}\n\nFILES - PDFs/Documents (for assignment attachments):\n${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; userId?: string | null }\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 } = await 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 {\n        text: streamedText,\n        parts: rawStreamParts,\n        cancelled,\n      } = await withTimeout(\n        streamChatResponse({\n          conversationId,\n          aiMessageId: emitOptions.aiMessageId,\n          model: AI_CHAT_MODEL,\n          system,\n          messages,\n          usageReason: 'lab_chat_response',\n          attribution: {\n            userId: emitOptions.userId ?? fullLabChat.createdById,\n            classId: emitOptions.classId,\n          },\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      if (cancelled) {\n        // User stopped the generation: persist whatever streamed so far and\n        // skip document generation / proposal creation entirely.\n        const partialParts = finalizeDeferredToolParts(rawStreamParts);\n        await cancelPendingAIMessage(emitOptions.aiMessageId, streamedText, {\n          meta: {\n            streamParts: partialParts.length > 0 ? partialParts : null,\n          },\n        });\n        await pusher\n          .trigger(teacherChannel(emitOptions.classId), \"lab-response-completed\", {\n            labChatId,\n            messageId: emitOptions.aiMessageId,\n          })\n          .catch(() => {});\n        logger.info('AI response cancelled by user', {\n          labChatId,\n          conversationId,\n          aiMessageId: emitOptions.aiMessageId,\n        });\n        return;\n      }\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        // Generated files are filed into the class cloud storage so teachers\n        // can find them in the class Files UI, not just as chat attachments.\n        let aiFolderId: string | undefined;\n        if (proposals.docs.length > 0) {\n          try {\n            const root = await findOrCreateScopeRoot({\n              kind: \"CLASS\",\n              classId: fullLabChat.classId,\n            });\n            const aiFolder = await findOrCreateChildFolderByName(\n              root.id,\n              AI_GENERATED_FOLDER_NAME,\n            );\n            aiFolderId = aiFolder.id;\n          } catch (folderError) {\n            logger.error(\"Failed to resolve AI generated class folder\", {\n              error: folderError,\n              labChatId,\n              classId: fullLabChat.classId,\n            });\n          }\n        }\n\n        for (let i = 0; i < proposals.docs.length; i++) {\n          const doc = proposals.docs[i];\n          if (!doc.title || !doc.content?.trim()) {\n            logger.error(`Document ${i + 1} is 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(`Document ${i + 1} generation returned null`, {\n                labChatId,\n                title: doc.title,\n                format,\n              });\n              continue;\n            }\n\n            const sanitizedTitle = doc.title\n              .replace(/[^a-zA-Z0-9\\s\\-_]/g, '')\n              .replace(/\\s+/g, '_')\n              .substring(0, 50);\n            const filename = `${sanitizedTitle}_${v4().substring(0, 8)}.${generated.format}`;\n            const filePath = `class/generated/${fullLabChat.classId}/${filename}`;\n\n            logger.info(`Document ${i + 1} generated successfully`, {\n              labChatId,\n              title: doc.title,\n              format: generated.format,\n            });\n\n            await bucket.file(filePath).save(generated.bytes, {\n              metadata: { contentType: generated.mimeType },\n            });\n\n            logger.info(`Document ${i + 1} uploaded successfully`, { labChatId, filename });\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                ...(aiFolderId && { folderId: aiFolderId }),\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              ...(aiFolderId && { folderId: aiFolderId }),\n            });\n          } catch (docError) {\n            logger.error(`Document generation failed for item ${i + 1}:`, {\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        // Defer-and-confirm: propose_* tool calls become pending creations the\n        // teacher approves or dismisses; nothing is created at generation time.\n        const { pendingCreations, parts: streamPartsWithProposals } =\n          buildPendingCreations(\n            proposals,\n            finalizeDeferredToolParts(\n              enrichStreamPartsWithGeneratedFiles(\n                applyResolvedFormatsToStreamParts(rawStreamParts, resolvedDocs),\n                generatedDocFiles,\n              ),\n            ),\n          );\n        const streamParts: StreamPart[] = streamPartsWithProposals;\n\n        // While the message is still PENDING, resolve deferred tool indicators\n        // (spinner → attachment or error) before the final persist event.\n        for (const part of streamParts) {\n          if (part.type !== 'tool' || part.toolName !== 'generate_document') {\n            continue;\n          }\n          if (part.status === 'executing') continue;\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              ...(part.fileId ? { fileId: part.fileId, fileName: part.fileName } : {}),\n              ...(part.folderId ? { folderId: part.folderId } : {}),\n              status: part.status,\n            })\n            .catch(() => {});\n        }\n\n        await completePendingAIMessage(emitOptions.aiMessageId, streamedText, {\n          ...(attachmentIds.length > 0 && {\n            attachments: { connect: attachmentIds.map((id) => ({ id })) },\n          }),\n          meta: {\n            pendingCreations: pendingCreations.length > 0 ? pendingCreations : 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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package/dist/pipelines/aiLabChatContract.d.ts

@@ -244,14 +244,182 @@ export declare const docToCreateSchema: z.ZodObject<{
 }, "strip", z.ZodTypeAny, {
     title: string;
     content: string;
-    format: "jpg" | "jpeg" | "png" | "gif" | "html" | "pdf" | "docx" | "xlsx" | "pptx" | "md" | "txt" | "csv" | "json" | "doc" | "xml" | "tex" | "zip" | "tar" | "py" | "js" | "ts" | "css" | "sh";
+    format: "jpg" | "jpeg" | "png" | "gif" | "html" | "json" | "pdf" | "docx" | "doc" | "xlsx" | "pptx" | "csv" | "md" | "txt" | "xml" | "tex" | "zip" | "tar" | "py" | "js" | "ts" | "css" | "sh";
 }, {
     title: string;
     content: string;
-    format?: "jpg" | "jpeg" | "png" | "gif" | "html" | "pdf" | "docx" | "xlsx" | "pptx" | "md" | "txt" | "csv" | "json" | "doc" | "xml" | "tex" | "zip" | "tar" | "py" | "js" | "ts" | "css" | "sh" | undefined;
+    format?: "jpg" | "jpeg" | "png" | "gif" | "html" | "json" | "pdf" | "docx" | "doc" | "xlsx" | "pptx" | "csv" | "md" | "txt" | "xml" | "tex" | "zip" | "tar" | "py" | "js" | "ts" | "css" | "sh" | undefined;
+}>;
+export declare const assignmentUpdateSchema: z.ZodObject<{
+    id: z.ZodString;
+    targetTitle: z.ZodString;
+    title: z.ZodOptional<z.ZodString>;
+    instructions: z.ZodOptional<z.ZodString>;
+    dueDate: z.ZodOptional<z.ZodString>;
+    type: z.ZodOptional<z.ZodEnum<["HOMEWORK", "QUIZ", "TEST", "PROJECT", "ESSAY", "DISCUSSION", "PRESENTATION", "LAB", "OTHER"]>>;
+    maxGrade: z.ZodOptional<z.ZodNumber>;
+    acceptFiles: z.ZodOptional<z.ZodBoolean>;
+    acceptExtendedResponse: z.ZodOptional<z.ZodBoolean>;
+    acceptWorksheet: z.ZodOptional<z.ZodBoolean>;
+    sectionId: z.ZodOptional<z.ZodNullable<z.ZodString>>;
+}, "strip", z.ZodTypeAny, {
+    id: string;
+    targetTitle: string;
+    type?: "DISCUSSION" | "HOMEWORK" | "QUIZ" | "TEST" | "PROJECT" | "ESSAY" | "PRESENTATION" | "LAB" | "OTHER" | undefined;
+    title?: string | undefined;
+    dueDate?: string | undefined;
+    maxGrade?: number | undefined;
+    instructions?: string | undefined;
+    acceptFiles?: boolean | undefined;
+    acceptExtendedResponse?: boolean | undefined;
+    acceptWorksheet?: boolean | undefined;
+    sectionId?: string | null | undefined;
+}, {
+    id: string;
+    targetTitle: string;
+    type?: "DISCUSSION" | "HOMEWORK" | "QUIZ" | "TEST" | "PROJECT" | "ESSAY" | "PRESENTATION" | "LAB" | "OTHER" | undefined;
+    title?: string | undefined;
+    dueDate?: string | undefined;
+    maxGrade?: number | undefined;
+    instructions?: string | undefined;
+    acceptFiles?: boolean | undefined;
+    acceptExtendedResponse?: boolean | undefined;
+    acceptWorksheet?: boolean | undefined;
+    sectionId?: string | null | undefined;
+}>;
+export declare const worksheetUpdateSchema: z.ZodObject<{
+    id: z.ZodString;
+    targetTitle: z.ZodString;
+    name: z.ZodOptional<z.ZodString>;
+    addQuestions: z.ZodDefault<z.ZodOptional<z.ZodArray<z.ZodObject<{
+        type: z.ZodEnum<["MULTIPLE_CHOICE", "TRUE_FALSE", "SHORT_ANSWER", "LONG_ANSWER", "MATH_EXPRESSION", "ESSAY"]>;
+        question: z.ZodString;
+        answer: z.ZodString;
+        options: z.ZodDefault<z.ZodOptional<z.ZodArray<z.ZodObject<{
+            id: z.ZodString;
+            text: z.ZodString;
+            isCorrect: z.ZodBoolean;
+        }, "strip", z.ZodTypeAny, {
+            id: string;
+            text: string;
+            isCorrect: boolean;
+        }, {
+            id: string;
+            text: string;
+            isCorrect: boolean;
+        }>, "many">>>;
+        markScheme: z.ZodDefault<z.ZodOptional<z.ZodArray<z.ZodObject<{
+            id: z.ZodString;
+            points: z.ZodNumber;
+            description: z.ZodString;
+        }, "strip", z.ZodTypeAny, {
+            id: string;
+            description: string;
+            points: number;
+        }, {
+            id: string;
+            description: string;
+            points: number;
+        }>, "many">>>;
+        points: z.ZodDefault<z.ZodOptional<z.ZodNumber>>;
+        order: z.ZodNumber;
+    }, "strip", z.ZodTypeAny, {
+        type: "ESSAY" | "MULTIPLE_CHOICE" | "TRUE_FALSE" | "SHORT_ANSWER" | "LONG_ANSWER" | "MATH_EXPRESSION";
+        options: {
+            id: string;
+            text: string;
+            isCorrect: boolean;
+        }[];
+        markScheme: {
+            id: string;
+            description: string;
+            points: number;
+        }[];
+        points: number;
+        question: string;
+        order: number;
+        answer: string;
+    }, {
+        type: "ESSAY" | "MULTIPLE_CHOICE" | "TRUE_FALSE" | "SHORT_ANSWER" | "LONG_ANSWER" | "MATH_EXPRESSION";
+        question: string;
+        order: number;
+        answer: string;
+        options?: {
+            id: string;
+            text: string;
+            isCorrect: boolean;
+        }[] | undefined;
+        markScheme?: {
+            id: string;
+            description: string;
+            points: number;
+        }[] | undefined;
+        points?: number | undefined;
+    }>, "many">>>;
+}, "strip", z.ZodTypeAny, {
+    id: string;
+    targetTitle: string;
+    addQuestions: {
+        type: "ESSAY" | "MULTIPLE_CHOICE" | "TRUE_FALSE" | "SHORT_ANSWER" | "LONG_ANSWER" | "MATH_EXPRESSION";
+        options: {
+            id: string;
+            text: string;
+            isCorrect: boolean;
+        }[];
+        markScheme: {
+            id: string;
+            description: string;
+            points: number;
+        }[];
+        points: number;
+        question: string;
+        order: number;
+        answer: string;
+    }[];
+    name?: string | undefined;
+}, {
+    id: string;
+    targetTitle: string;
+    name?: string | undefined;
+    addQuestions?: {
+        type: "ESSAY" | "MULTIPLE_CHOICE" | "TRUE_FALSE" | "SHORT_ANSWER" | "LONG_ANSWER" | "MATH_EXPRESSION";
+        question: string;
+        order: number;
+        answer: string;
+        options?: {
+            id: string;
+            text: string;
+            isCorrect: boolean;
+        }[] | undefined;
+        markScheme?: {
+            id: string;
+            description: string;
+            points: number;
+        }[] | undefined;
+        points?: number | undefined;
+    }[] | undefined;
+}>;
+export declare const sectionUpdateSchema: z.ZodObject<{
+    id: z.ZodString;
+    targetTitle: z.ZodString;
+    name: z.ZodString;
+    color: z.ZodOptional<z.ZodNullable<z.ZodString>>;
+}, "strip", z.ZodTypeAny, {
+    id: string;
+    name: string;
+    targetTitle: string;
+    color?: string | null | undefined;
+}, {
+    id: string;
+    name: string;
+    targetTitle: string;
+    color?: string | null | undefined;
 }>;
 export type WorksheetToCreate = z.infer<typeof worksheetToCreateSchema>;
 export type SectionToCreate = z.infer<typeof sectionToCreateSchema>;
 export type AssignmentToCreate = z.infer<typeof assignmentToCreateSchema>;
 export type DocToCreate = z.infer<typeof docToCreateSchema>;
+export type AssignmentUpdate = z.infer<typeof assignmentUpdateSchema>;
+export type WorksheetUpdate = z.infer<typeof worksheetUpdateSchema>;
+export type SectionUpdate = z.infer<typeof sectionUpdateSchema>;
 //# sourceMappingURL=aiLabChatContract.d.ts.map

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

@@ -1 +1 @@
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+{"version":3,"file":"aiLabChatContract.d.ts","sourceRoot":"/","sources":["pipelines/aiLabChatContract.ts"],"names":[],"mappings":"AAAA,OAAO,CAAC,MAAM,KAAK,CAAC;AAEpB,eAAO,MAAM,uBAAuB;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;EAgBlC,CAAC;AAEH,eAAO,MAAM,uBAAuB;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;EAGlC,CAAC;AAEH,eAAO,MAAM,qBAAqB;;;;;;;;;EAGhC,CAAC;AAEH,eAAO,MAAM,wBAAwB;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;EAiBnC,CAAC;AAEH,eAAO,MAAM,oBAAoB,+KAI/B,CAAC;AAEH,eAAO,MAAM,iBAAiB;;;;;;;;;;;;EAI5B,CAAC;AAMH,eAAO,MAAM,sBAAsB;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;EAYjC,CAAC;AAEH,eAAO,MAAM,qBAAqB;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;EAKhC,CAAC;AAEH,eAAO,MAAM,mBAAmB;;;;;;;;;;;;;;;EAK9B,CAAC;AAEH,MAAM,MAAM,iBAAiB,GAAG,CAAC,CAAC,KAAK,CAAC,OAAO,uBAAuB,CAAC,CAAC;AACxE,MAAM,MAAM,eAAe,GAAG,CAAC,CAAC,KAAK,CAAC,OAAO,qBAAqB,CAAC,CAAC;AACpE,MAAM,MAAM,kBAAkB,GAAG,CAAC,CAAC,KAAK,CAAC,OAAO,wBAAwB,CAAC,CAAC;AAC1E,MAAM,MAAM,WAAW,GAAG,CAAC,CAAC,KAAK,CAAC,OAAO,iBAAiB,CAAC,CAAC;AAC5D,MAAM,MAAM,gBAAgB,GAAG,CAAC,CAAC,KAAK,CAAC,OAAO,sBAAsB,CAAC,CAAC;AACtE,MAAM,MAAM,eAAe,GAAG,CAAC,CAAC,KAAK,CAAC,OAAO,qBAAqB,CAAC,CAAC;AACpE,MAAM,MAAM,aAAa,GAAG,CAAC,CAAC,KAAK,CAAC,OAAO,mBAAmB,CAAC,CAAC"}

package/dist/pipelines/aiLabChatContract.js

@@ -1,5 +1,5 @@
 
-!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]="014b6af6-35ab-5e0f-8113-8bfd1d48964d")}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]="c00c6112-86d0-5fea-b720-24d9bd40bfdc")}catch(e){}}();
 import z from "zod";
 export const worksheetQuestionSchema = z.object({
     type: z.enum(["MULTIPLE_CHOICE", "TRUE_FALSE", "SHORT_ANSWER", "LONG_ANSWER", "MATH_EXPRESSION", "ESSAY"]),
@@ -54,5 +54,33 @@ export const docToCreateSchema = z.object({
     content: z.string().min(1),
     format: documentFormatSchema.optional().default('pdf'),
 });
+const assignmentTypeSchema = z.enum(["HOMEWORK", "QUIZ", "TEST", "PROJECT", "ESSAY", "DISCUSSION", "PRESENTATION", "LAB", "OTHER"]);
+// Update payloads: `id` targets an existing entity; `targetTitle` is the
+// entity's current name for the approval card. Only provided fields change.
+export const assignmentUpdateSchema = z.object({
+    id: z.string(),
+    targetTitle: z.string(),
+    title: z.string().optional(),
+    instructions: z.string().optional(),
+    dueDate: z.string().datetime().optional(),
+    type: assignmentTypeSchema.optional(),
+    maxGrade: z.number().optional(),
+    acceptFiles: z.boolean().optional(),
+    acceptExtendedResponse: z.boolean().optional(),
+    acceptWorksheet: z.boolean().optional(),
+    sectionId: z.string().nullable().optional(),
+});
+export const worksheetUpdateSchema = z.object({
+    id: z.string(),
+    targetTitle: z.string(),
+    name: z.string().optional(),
+    addQuestions: z.array(worksheetQuestionSchema).optional().default([]),
+});
+export const sectionUpdateSchema = z.object({
+    id: z.string(),
+    targetTitle: z.string(),
+    name: z.string(),
+    color: z.string().regex(/^#([0-9a-fA-F]{3}|[0-9a-fA-F]{6})$/).nullable().optional(),
+});
 //# sourceMappingURL=aiLabChatContract.js.map
-//# debugId=014b6af6-35ab-5e0f-8113-8bfd1d48964d
+//# debugId=c00c6112-86d0-5fea-b720-24d9bd40bfdc

package/dist/pipelines/aiLabChatContract.js.map

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'sh',\n]);\n\nexport const docToCreateSchema = z.object({\n  title: z.string(),\n  content: z.string().min(1),\n  format: documentFormatSchema.optional().default('pdf'),\n});\n\nexport type WorksheetToCreate = z.infer<typeof worksheetToCreateSchema>;\nexport type SectionToCreate = z.infer<typeof sectionToCreateSchema>;\nexport type AssignmentToCreate = z.infer<typeof assignmentToCreateSchema>;\nexport type DocToCreate = z.infer<typeof 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+{"version":3,"file":"aiLabChatContract.js","sources":["pipelines/aiLabChatContract.ts"],"sourceRoot":"/","sourcesContent":["import z from \"zod\";\n\nexport const worksheetQuestionSchema = z.object({\n  type: z.enum([\"MULTIPLE_CHOICE\", \"TRUE_FALSE\", \"SHORT_ANSWER\", \"LONG_ANSWER\", \"MATH_EXPRESSION\", \"ESSAY\"]),\n  question: z.string(),\n  answer: z.string(),\n  options: z.array(z.object({\n    id: z.string(),\n    text: z.string(),\n    isCorrect: z.boolean(),\n  })).optional().default([]),\n  markScheme: z.array(z.object({\n    id: z.string(),\n    points: z.number(),\n    description: z.string(),\n  })).optional().default([]),\n  points: z.number().optional().default(0),\n  order: z.number(),\n});\n\nexport const worksheetToCreateSchema = z.object({\n  title: z.string(),\n  questions: z.array(worksheetQuestionSchema),\n});\n\nexport const sectionToCreateSchema = z.object({\n  name: z.string(),\n  color: z.string().regex(/^#([0-9a-fA-F]{3}|[0-9a-fA-F]{6})$/).nullable().optional(),\n});\n\nexport const assignmentToCreateSchema = z.object({\n  title: z.string(),\n  instructions: z.string(),\n  dueDate: z.string().datetime(),\n  acceptFiles: z.boolean(),\n  acceptExtendedResponse: z.boolean(),\n  acceptWorksheet: z.boolean(),\n  maxGrade: z.number(),\n  gradingBoundaryId: z.string().nullable().optional(),\n  markSchemeId: z.string().nullable().optional(),\n  worksheetIds: z.array(z.string()),\n  studentIds: z.array(z.string()),\n  sectionId: z.string().nullable().optional(),\n  type: z.enum([\"HOMEWORK\", \"QUIZ\", \"TEST\", \"PROJECT\", \"ESSAY\", \"DISCUSSION\", \"PRESENTATION\", \"LAB\", \"OTHER\"]),\n  attachments: z.array(z.object({\n    id: z.string(),\n  })),\n});\n\nexport const documentFormatSchema = z.enum([\n  'pdf', 'docx', 'doc', 'xlsx', 'pptx', 'csv', 'md', 'html', 'txt', 'json',\n  'xml', 'tex', 'png', 'jpeg', 'jpg', 'gif', 'zip', 'tar', 'py', 'js', 'ts',\n  'css', 'sh',\n]);\n\nexport const docToCreateSchema = z.object({\n  title: z.string(),\n  content: z.string().min(1),\n  format: documentFormatSchema.optional().default('pdf'),\n});\n\nconst assignmentTypeSchema = z.enum([\"HOMEWORK\", \"QUIZ\", \"TEST\", \"PROJECT\", \"ESSAY\", \"DISCUSSION\", \"PRESENTATION\", \"LAB\", \"OTHER\"]);\n\n// Update payloads: `id` targets an existing entity; `targetTitle` is the\n// entity's current name for the approval card. Only provided fields change.\nexport const assignmentUpdateSchema = z.object({\n  id: z.string(),\n  targetTitle: z.string(),\n  title: z.string().optional(),\n  instructions: z.string().optional(),\n  dueDate: z.string().datetime().optional(),\n  type: assignmentTypeSchema.optional(),\n  maxGrade: z.number().optional(),\n  acceptFiles: z.boolean().optional(),\n  acceptExtendedResponse: z.boolean().optional(),\n  acceptWorksheet: z.boolean().optional(),\n  sectionId: z.string().nullable().optional(),\n});\n\nexport const worksheetUpdateSchema = z.object({\n  id: z.string(),\n  targetTitle: z.string(),\n  name: z.string().optional(),\n  addQuestions: z.array(worksheetQuestionSchema).optional().default([]),\n});\n\nexport const sectionUpdateSchema = z.object({\n  id: z.string(),\n  targetTitle: z.string(),\n  name: z.string(),\n  color: z.string().regex(/^#([0-9a-fA-F]{3}|[0-9a-fA-F]{6})$/).nullable().optional(),\n});\n\nexport type WorksheetToCreate = z.infer<typeof worksheetToCreateSchema>;\nexport type SectionToCreate = z.infer<typeof sectionToCreateSchema>;\nexport type AssignmentToCreate = z.infer<typeof assignmentToCreateSchema>;\nexport type DocToCreate = z.infer<typeof docToCreateSchema>;\nexport type AssignmentUpdate = z.infer<typeof assignmentUpdateSchema>;\nexport type WorksheetUpdate = z.infer<typeof worksheetUpdateSchema>;\nexport type SectionUpdate = z.infer<typeof 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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":"AAwBA,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,EACnB,eAAe,MAAM,GAAG,IAAI,KAC3B,OAAO,CAAC,IAAI,CA6Gd,CAAA;AA8BD;;;;;;GAMG;AACH,eAAO,MAAM,6BAA6B,GACxC,cAAc,MAAM,EACpB,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,EACnB,eAAe,MAAM,GAAG,IAAI,KAC3B,OAAO,CAAC,IAAI,CAoJd,CAAA"}

package/dist/pipelines/aiNewtonChat.js

@@ -3,9 +3,9 @@
  * 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]="6f19981e-add0-5246-bbdc-fd8dc49a48b9")}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]="2a45f704-559d-535f-ab1b-a00d4e7d1b03")}catch(e){}}();
 import { prisma } from "../lib/prisma.js";
-import { completePendingAIMessage, failPendingAIMessage, } from "../utils/inference.js";
+import { cancelPendingAIMessage, completePendingAIMessage, failPendingAIMessage, } from "../utils/inference.js";
 import { logger } from "../utils/logger.js";
 import { isAIUser } from "../utils/aiUser.js";
 import { broadcastStreamComplete } from "../utils/streamBroadcast.js";
@@ -118,7 +118,7 @@ export const generateAndSendNewtonIntroduction = async (newtonChatId, conversati
   - Use clear, educational language appropriate for the subject
   
   Do not use markdown formatting in your responses - use plain text only.`;
-        const { text: response } = await streamChatResponse({
+        const { text: response, cancelled } = await streamChatResponse({
             conversationId,
             aiMessageId,
             model: AI_CHAT_MODEL,
@@ -137,6 +137,13 @@ export const generateAndSendNewtonIntroduction = async (newtonChatId, conversati
                 classId: submission.assignment.classId,
             },
         });
+        if (cancelled) {
+            // User stopped the intro: keep the partial text, no fallback message.
+            await cancelPendingAIMessage(aiMessageId, response);
+            await broadcastStreamComplete(conversationId, aiMessageId);
+            logger.info('AI introduction cancelled by user', { newtonChatId, aiMessageId });
+            return;
+        }
         if (!response) {
             throw new Error('No response generated from inference API');
         }
@@ -149,6 +156,15 @@ export const generateAndSendNewtonIntroduction = async (newtonChatId, conversati
         // Fallback: still complete the placeholder so the student isn't stuck
         // staring at an empty bubble.
         try {
+            // A cancelled placeholder stays cancelled — no fallback greeting.
+            const current = await prisma.message.findUnique({
+                where: { id: aiMessageId },
+                select: { status: true },
+            });
+            if (current?.status === 'CANCELLED') {
+                logger.info('Skipping fallback intro; message cancelled', { newtonChatId, aiMessageId });
+                return;
+            }
             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 completePendingAIMessage(aiMessageId, fallbackIntro);
             logger.info('Fallback AI introduction sent', { newtonChatId, aiMessageId });
@@ -280,7 +296,7 @@ export const generateAndSendNewtonResponse = async (newtonChatId, conversationId
         // Newton gets read-only RAG tools so it can ground tutoring in the
         // class's materials/assignments. No proposal/write tools for students.
         const newtonClassId = assignmentData?.classId;
-        const { text: response, parts: streamParts } = await streamChatResponse({
+        const { text: response, parts: streamParts, cancelled, } = await streamChatResponse({
             conversationId,
             aiMessageId,
             model: AI_CHAT_MODEL,
@@ -292,6 +308,15 @@ export const generateAndSendNewtonResponse = async (newtonChatId, conversationId
             usageReason: 'newton_response',
             attribution: { userId: actingUserId, classId: newtonClassId },
         });
+        if (cancelled) {
+            // User stopped the generation: keep whatever streamed so far.
+            await cancelPendingAIMessage(aiMessageId, response, {
+                meta: { streamParts: streamParts.length > 0 ? streamParts : null },
+            });
+            await broadcastStreamComplete(conversationId, aiMessageId);
+            logger.info('AI response cancelled by user', { newtonChatId, aiMessageId });
+            return;
+        }
         if (!response) {
             throw new Error('No response generated from inference API');
         }
@@ -318,4 +343,4 @@ export const generateAndSendNewtonResponse = async (newtonChatId, conversationId
     }
 };
 //# sourceMappingURL=aiNewtonChat.js.map
-//# debugId=6f19981e-add0-5246-bbdc-fd8dc49a48b9
+//# debugId=2a45f704-559d-535f-ab1b-a00d4e7d1b03