fix(knowledge): enqueue docs per-batch instead of post-loop to survive sync timeouts

apps/sim/lib/knowledge/connectors/sync-engine.ts

@@ -6,13 +6,14 @@ import {
   knowledgeConnectorSyncLog,
 } from '@sim/db/schema'
 import { createLogger } from '@sim/logger'
-import { and, eq, inArray, isNull, lt, ne, sql } from 'drizzle-orm'
+import { and, eq, gt, inArray, isNull, lt, ne, or, sql } from 'drizzle-orm'
 import { decryptApiKey } from '@/lib/api-key/crypto'
 import { getInternalApiBaseUrl } from '@/lib/core/utils/urls'
+import type { DocumentData } from '@/lib/knowledge/documents/service'
 import {
   hardDeleteDocuments,
   isTriggerAvailable,
-  processDocumentAsync,
+  processDocumentsWithQueue,
 } from '@/lib/knowledge/documents/service'
 import { StorageService } from '@/lib/uploads'
 import { deleteFile } from '@/lib/uploads/core/storage-service'
@@ -39,6 +40,8 @@ class ConnectorDeletedException extends Error {
 const SYNC_BATCH_SIZE = 5
 const MAX_PAGES = 500
 const MAX_SAFE_TITLE_LENGTH = 200
+const STALE_PROCESSING_MINUTES = 45
+const RETRY_WINDOW_DAYS = 7
 
 /** Sanitizes a document title for use in S3 storage keys. */
 function sanitizeStorageTitle(title: string): string {
@@ -147,11 +150,14 @@ export async function dispatchSync(
   const requestId = options?.requestId ?? crypto.randomUUID()
 
   if (isTriggerAvailable()) {
-    await knowledgeConnectorSync.trigger({
-      connectorId,
-      fullSync: options?.fullSync,
-      requestId,
-    })
+    await knowledgeConnectorSync.trigger(
+      {
+        connectorId,
+        fullSync: options?.fullSync,
+        requestId,
+      },
+      { tags: [`connector:${connectorId}`] }
+    )
     logger.info(`Dispatched connector sync to Trigger.dev`, { connectorId, requestId })
   } else {
     executeSync(connectorId, { fullSync: options?.fullSync }).catch((error) => {
@@ -500,9 +506,11 @@ export async function executeSync(
         })
       )
 
+      const batchDocs: DocumentData[] = []
       for (let j = 0; j < settled.length; j++) {
         const outcome = settled[j]
         if (outcome.status === 'fulfilled') {
+          batchDocs.push(outcome.value)
           if (batch[j].type === 'add') result.docsAdded++
           else result.docsUpdated++
         } else {
@@ -515,6 +523,26 @@ export async function executeSync(
           })
         }
       }
+
+      // Enqueue this batch for processing immediately so that even if the sync
+      // task times out, all documents inserted up to this point are already
+      // queued for processing and won't be orphaned.
+      if (batchDocs.length > 0) {
+        try {
+          await processDocumentsWithQueue(
+            batchDocs,
+            connector.knowledgeBaseId,
+            {},
+            crypto.randomUUID()
+          )
+        } catch (error) {
+          logger.warn('Failed to enqueue batch for processing — will retry on next sync', {
+            connectorId,
+            count: batchDocs.length,
+            error: error instanceof Error ? error.message : String(error),
+          })
+        }
+      }
     }
 
     // Skip deletion reconciliation during incremental syncs — results only contain changed docs
@@ -537,9 +565,14 @@ export async function executeSync(
       throw new Error(`Knowledge base ${connector.knowledgeBaseId} was deleted during sync`)
     }
 
-    // Retry stuck documents that failed or never completed processing.
+    // Retry stuck documents that failed, never started, or were abandoned mid-processing.
     // Only retry docs uploaded BEFORE this sync — docs added in the current sync
     // are still processing asynchronously and would cause a duplicate processing race.
+    // Documents stuck in 'processing' beyond STALE_PROCESSING_MINUTES are considered
+    // abandoned (e.g. the Trigger.dev task process exited before processing completed).
+    // Documents uploaded more than RETRY_WINDOW_DAYS ago are not retried.
+    const staleProcessingCutoff = new Date(Date.now() - STALE_PROCESSING_MINUTES * 60 * 1000)
+    const retryCutoff = new Date(Date.now() - RETRY_WINDOW_DAYS * 24 * 60 * 60 * 1000)
     const stuckDocs = await db
       .select({
         id: document.id,
@@ -552,8 +585,18 @@ export async function executeSync(
       .where(
         and(
           eq(document.connectorId, connectorId),
-          inArray(document.processingStatus, ['pending', 'failed']),
+          or(
+            inArray(document.processingStatus, ['pending', 'failed']),
+            and(
+              eq(document.processingStatus, 'processing'),
+              or(
+                isNull(document.processingStartedAt),
+                lt(document.processingStartedAt, staleProcessingCutoff)
+              )
+            )
+          ),
           lt(document.uploadedAt, syncStartedAt),
+          gt(document.uploadedAt, retryCutoff),
           eq(document.userExcluded, false),
           isNull(document.archivedAt),
           isNull(document.deletedAt)
@@ -562,28 +605,42 @@ export async function executeSync(
 
     if (stuckDocs.length > 0) {
       logger.info(`Retrying ${stuckDocs.length} stuck documents`, { connectorId })
-      for (const doc of stuckDocs) {
-        processDocumentAsync(
-          connector.knowledgeBaseId,
-          doc.id,
-          {
+      try {
+        await processDocumentsWithQueue(
+          stuckDocs.map((doc) => ({
+            documentId: doc.id,
             filename: doc.filename ?? 'document.txt',
             fileUrl: doc.fileUrl ?? '',
             fileSize: doc.fileSize ?? 0,
             mimeType: doc.mimeType ?? 'text/plain',
-          },
-          {}
-        ).catch((error) => {
-          logger.warn('Failed to retry stuck document', {
-            documentId: doc.id,
-            error: error instanceof Error ? error.message : String(error),
-          })
+          })),
+          connector.knowledgeBaseId,
+          {},
+          crypto.randomUUID()
+        )
+      } catch (error) {
+        logger.warn('Failed to enqueue stuck documents for reprocessing', {
+          connectorId,
+          count: stuckDocs.length,
+          error: error instanceof Error ? error.message : String(error),
         })
       }
     }
 
     await completeSyncLog(syncLogId, 'completed', result)
 
+    const [{ count: actualDocCount }] = await db
+      .select({ count: sql<number>`count(*)::int` })
+      .from(document)
+      .where(
+        and(
+          eq(document.connectorId, connectorId),
+          eq(document.userExcluded, false),
+          isNull(document.archivedAt),
+          isNull(document.deletedAt)
+        )
+      )
+
     const now = new Date()
     await db
       .update(knowledgeConnector)
@@ -591,7 +648,7 @@ export async function executeSync(
         status: 'active',
         lastSyncAt: now,
         lastSyncError: null,
-        lastSyncDocCount: externalDocs.length,
+        lastSyncDocCount: actualDocCount,
         nextSyncAt: calculateNextSyncTime(connector.syncIntervalMinutes),
         consecutiveFailures: 0,
         updatedAt: now,
@@ -711,7 +768,7 @@ async function addDocument(
   connectorType: string,
   extDoc: ExternalDocument,
   sourceConfig?: Record<string, unknown>
-): Promise<void> {
+): Promise<DocumentData> {
   if (await isKnowledgeBaseDeleted(knowledgeBaseId)) {
     throw new Error(`Knowledge base ${knowledgeBaseId} is deleted`)
   }
@@ -773,23 +830,13 @@ async function addDocument(
     throw error
   }
 
-  processDocumentAsync(
-    knowledgeBaseId,
+  return {
     documentId,
-    {
-      filename: processingFilename,
-      fileUrl,
-      fileSize: contentBuffer.length,
-      mimeType: 'text/plain',
-    },
-    {}
-  ).catch((error) => {
-    logger.error('Failed to process connector document', {
-      documentId,
-      connectorId,
-      error: error instanceof Error ? error.message : String(error),
-    })
-  })
+    filename: processingFilename,
+    fileUrl,
+    fileSize: contentBuffer.length,
+    mimeType: 'text/plain',
+  }
 }
 
 /**
@@ -803,7 +850,7 @@ async function updateDocument(
   connectorType: string,
   extDoc: ExternalDocument,
   sourceConfig?: Record<string, unknown>
-): Promise<void> {
+): Promise<DocumentData> {
   if (await isKnowledgeBaseDeleted(knowledgeBaseId)) {
     throw new Error(`Knowledge base ${knowledgeBaseId} is deleted`)
   }
@@ -894,21 +941,11 @@ async function updateDocument(
     }
   }
 
-  processDocumentAsync(
-    knowledgeBaseId,
-    existingDocId,
-    {
-      filename: processingFilename,
-      fileUrl,
-      fileSize: contentBuffer.length,
-      mimeType: 'text/plain',
-    },
-    {}
-  ).catch((error) => {
-    logger.error('Failed to re-process updated connector document', {
-      documentId: existingDocId,
-      connectorId,
-      error: error instanceof Error ? error.message : String(error),
-    })
-  })
+  return {
+    documentId: existingDocId,
+    filename: processingFilename,
+    fileUrl,
+    fileSize: contentBuffer.length,
+    mimeType: 'text/plain',
+  }
 }

apps/sim/lib/knowledge/documents/service.ts

@@ -114,11 +114,11 @@ export interface DocumentData {
 }
 
 export interface ProcessingOptions {
-  chunkSize: number
-  minCharactersPerChunk: number
-  recipe: string
-  lang: string
-  chunkOverlap: number
+  chunkSize?: number
+  minCharactersPerChunk?: number
+  recipe?: string
+  lang?: string
+  chunkOverlap?: number
 }
 
 export interface DocumentJobData {
@@ -668,7 +668,7 @@ export function isTriggerAvailable(): boolean {
 export async function processDocumentsWithTrigger(
   documents: DocumentProcessingPayload[],
   requestId: string
-): Promise<{ success: boolean; message: string; jobIds?: string[] }> {
+): Promise<{ success: boolean; message: string; batchIds?: string[] }> {
   if (!isTriggerAvailable()) {
     throw new Error('Trigger.dev is not configured - TRIGGER_SECRET_KEY missing')
   }
@@ -676,19 +676,32 @@ export async function processDocumentsWithTrigger(
   try {
     logger.info(`[${requestId}] Triggering background processing for ${documents.length} documents`)
 
-    const jobPromises = documents.map(async (document) => {
-      const job = await tasks.trigger('knowledge-process-document', document)
-      return job.id
-    })
+    const MAX_BATCH_SIZE = 1000
+    const batchIds: string[] = []
 
-    const jobIds = await Promise.all(jobPromises)
+    for (let i = 0; i < documents.length; i += MAX_BATCH_SIZE) {
+      const chunk = documents.slice(i, i + MAX_BATCH_SIZE)
+      const batchResult = await tasks.batchTrigger(
+        'knowledge-process-document',
+        chunk.map((doc) => ({
+          payload: doc,
+          options: {
+            idempotencyKey: `doc-process-${doc.documentId}-${requestId}`,
+            tags: [`kb:${doc.knowledgeBaseId}`, `doc:${doc.documentId}`],
+          },
+        }))
+      )
+      batchIds.push(batchResult.batchId)
+    }
 
-    logger.info(`[${requestId}] Triggered ${jobIds.length} document processing jobs`)
+    logger.info(
+      `[${requestId}] Triggered ${documents.length} document processing jobs in ${batchIds.length} batch(es)`
+    )
 
     return {
       success: true,
       message: `${documents.length} document processing jobs triggered`,
-      jobIds,
+      batchIds,
     }
   } catch (error) {
     logger.error(`[${requestId}] Failed to trigger document processing jobs:`, error)
@@ -1590,10 +1603,19 @@ export async function retryDocumentProcessing(
     chunkOverlap: kbConfig.overlap,
   }
 
-  processDocumentAsync(knowledgeBaseId, documentId, docData, processingOptions).catch(
-    (error: unknown) => {
-      logger.error(`[${requestId}] Background retry processing error:`, error)
-    }
+  await processDocumentsWithQueue(
+    [
+      {
+        documentId,
+        filename: docData.filename,
+        fileUrl: docData.fileUrl,
+        fileSize: docData.fileSize,
+        mimeType: docData.mimeType,
+      },
+    ],
+    knowledgeBaseId,
+    processingOptions,
+    requestId
   )
 
   logger.info(`[${requestId}] Document retry initiated: ${documentId}`)