From 24f061116f606c3262ee575d499a61a5e881c12f Mon Sep 17 00:00:00 2001
From: Waleed Latif <walif6@gmail.com>
Date: Mon, 21 Sep 2026 19:39:03 -0700
Subject: [PATCH 1/5] fix(knowledge): bound source titles and tag values so an
 oversized index row cannot fail a connector sync

---
 .../connectors/sync-persistence.test.ts       | 40 ++++++++++++++++++-
 .../knowledge/connectors/sync-persistence.ts  | 23 +++++++++--
 2 files changed, 58 insertions(+), 5 deletions(-)

diff --git a/apps/sim/lib/knowledge/connectors/sync-persistence.test.ts b/apps/sim/lib/knowledge/connectors/sync-persistence.test.ts
index 34c9e6a2423..f4593174554 100644
--- a/apps/sim/lib/knowledge/connectors/sync-persistence.test.ts
+++ b/apps/sim/lib/knowledge/connectors/sync-persistence.test.ts
@@ -27,7 +27,11 @@ vi.mock('@/lib/knowledge/documents/storage-cleanup', () => ({
   }),
   isKnowledgeBaseOwnedStorageKey: (key: string) => key.startsWith('kb/'),
 }))
-vi.mock('@/connectors/registry.server', () => ({ CONNECTOR_REGISTRY: {} }))
+vi.mock('@/connectors/registry.server', () => ({
+  CONNECTOR_REGISTRY: {
+    fixture: { mapTags: (metadata: Record<string, unknown>) => ({ label: metadata.label }) },
+  },
+}))
 
 import { MAX_ACL_TOKENS } from '@/lib/knowledge/access/tokens'
 import { getConnectorFailureDiagnostic } from '@/lib/knowledge/connectors/connector-error'
@@ -35,6 +39,7 @@ import {
   addDocument,
   persistDocumentAcls,
   persistSourceDocumentFailures,
+  resolveTagMapping,
 } from '@/lib/knowledge/connectors/sync-persistence'
 
 const CONNECTOR = 'connector-1'
@@ -350,6 +355,18 @@ describe('persistSourceDocumentFailures', () => {
     expect(JSON.stringify(dbChainMockFns.set.mock.calls)).not.toContain('private body')
     expect(dbChainMockFns.delete).not.toHaveBeenCalled()
   })
+  it('bounds a source title that would exceed the filename index row limit', async () => {
+    leaseHeld()
+    const title = 'x'.repeat(5000)
+    await persistSourceDocumentFailures({
+      ...input,
+      documents: [{ ...input.documents[0], title }],
+      priorByExternalId: new Map(),
+    })
+    const [rows] = dbChainMockFns.values.mock.calls[0] as [Array<{ filename: string }>]
+    expect(rows[0].filename.length).toBeLessThan(600)
+    expect(rows[0].filename.startsWith('xxxx')).toBe(true)
+  })
   it('refuses to commit a failure under a reclaimed lease', async () => {
     queueTableRows(schemaMock.knowledgeBase, [{ id: 'kb' }])
     await expect(
@@ -416,3 +433,24 @@ describe('organization source cache persistence', () => {
     expect(mockUploadFile).not.toHaveBeenCalled()
   })
 })
+
+describe('resolveTagMapping', () => {
+  it('bounds a mapped tag value that would exceed its index row limit', () => {
+    const tags = resolveTagMapping(
+      'fixture',
+      { label: 'y'.repeat(5000) },
+      { tagSlotMapping: { label: 'tag1' } }
+    )
+    expect(tags?.tag1?.length).toBeLessThan(600)
+    expect(tags?.tag1?.startsWith('yyyy')).toBe(true)
+  })
+
+  it('keeps a short mapped tag value intact', () => {
+    const tags = resolveTagMapping(
+      'fixture',
+      { label: 'Purchasing' },
+      { tagSlotMapping: { label: 'tag1' } }
+    )
+    expect(tags?.tag1).toBe('Purchasing')
+  })
+})
diff --git a/apps/sim/lib/knowledge/connectors/sync-persistence.ts b/apps/sim/lib/knowledge/connectors/sync-persistence.ts
index 33b53184ac2..526861107bd 100644
--- a/apps/sim/lib/knowledge/connectors/sync-persistence.ts
+++ b/apps/sim/lib/knowledge/connectors/sync-persistence.ts
@@ -3,6 +3,7 @@ import { document, embedding, knowledgeBase, knowledgeConnector } from '@sim/db/
 import { createLogger } from '@sim/logger'
 import { chunkArray } from '@sim/utils/helpers'
 import { generateId } from '@sim/utils/id'
+import { truncate } from '@sim/utils/string'
 import { and, eq, exists, inArray, isNull, lt, or, sql } from 'drizzle-orm'
 import { getInternalApiBaseUrl } from '@/lib/core/utils/urls'
 import type { DbOrTx } from '@/lib/db/types'
@@ -173,6 +174,19 @@ export async function persistDocumentAcls(
 
 const MAX_SAFE_TITLE_LENGTH = 200
 
+/**
+ * A document's filename and text tags sit under btree indexes, and Postgres refuses an index
+ * row past about 2.7 KB. A source title or tag value beyond that fails the row and, with it,
+ * every sync that lists the document again. 512 characters keeps a four-byte-per-character
+ * value inside the ceiling.
+ */
+const MAX_INDEXED_TEXT_LENGTH = 512
+
+/** Bounds a source-supplied value that lands in an indexed text column. */
+function boundIndexedText(value: string): string {
+  return truncate(value, MAX_INDEXED_TEXT_LENGTH)
+}
+
 function sanitizeStorageTitle(title: string): string {
   return title.replace(/[^a-zA-Z0-9.-]/g, '_').slice(0, MAX_SAFE_TITLE_LENGTH)
 }
@@ -250,7 +264,8 @@ export function resolveTagMapping(
   const result: Partial<DocumentTags> = {}
   for (const [semanticKey, slot] of Object.entries(mapping)) {
     const value = semanticTags[semanticKey]
-    ;(result as Record<string, unknown>)[slot] = value != null ? value : null
+    ;(result as Record<string, unknown>)[slot] =
+      typeof value === 'string' ? boundIndexedText(value) : value != null ? value : null
   }
   return result
 }
@@ -278,7 +293,7 @@ function buildSkippedDocumentRow(
   return {
     id: generateId(),
     knowledgeBaseId,
-    filename: extDoc.title,
+    filename: boundIndexedText(extDoc.title),
     fileUrl: '',
     storageKey: null,
     /** No artifact was stored; a provider's reported source size is not local storage usage. */
@@ -630,7 +645,7 @@ export async function addDocument(
     await tx.insert(document).values({
       id: documentId,
       knowledgeBaseId,
-      filename: extDoc.title,
+      filename: boundIndexedText(extDoc.title),
       fileUrl,
       storageKey: fileInfo.key,
       fileSize: artifact.bytes.length,
@@ -745,7 +760,7 @@ export async function updateDocument(
     await tx
       .update(document)
       .set({
-        filename: extDoc.title,
+        filename: boundIndexedText(extDoc.title),
         fileUrl,
         storageKey: fileInfo.key,
         fileSize: artifact.bytes.length,

From 720797482d2d5098a4c115b420fdd37a14ff895d Mon Sep 17 00:00:00 2001
From: Waleed Latif <walif6@gmail.com>
Date: Mon, 21 Sep 2026 19:44:48 -0700
Subject: [PATCH 2/5] test(knowledge): pin the exact indexed-text boundary

---
 apps/sim/lib/knowledge/connectors/sync-persistence.test.ts | 6 ++----
 1 file changed, 2 insertions(+), 4 deletions(-)

diff --git a/apps/sim/lib/knowledge/connectors/sync-persistence.test.ts b/apps/sim/lib/knowledge/connectors/sync-persistence.test.ts
index f4593174554..23a98dd5482 100644
--- a/apps/sim/lib/knowledge/connectors/sync-persistence.test.ts
+++ b/apps/sim/lib/knowledge/connectors/sync-persistence.test.ts
@@ -364,8 +364,7 @@ describe('persistSourceDocumentFailures', () => {
       priorByExternalId: new Map(),
     })
     const [rows] = dbChainMockFns.values.mock.calls[0] as [Array<{ filename: string }>]
-    expect(rows[0].filename.length).toBeLessThan(600)
-    expect(rows[0].filename.startsWith('xxxx')).toBe(true)
+    expect(rows[0].filename).toBe(`${'x'.repeat(512)}...`)
   })
   it('refuses to commit a failure under a reclaimed lease', async () => {
     queueTableRows(schemaMock.knowledgeBase, [{ id: 'kb' }])
@@ -441,8 +440,7 @@ describe('resolveTagMapping', () => {
       { label: 'y'.repeat(5000) },
       { tagSlotMapping: { label: 'tag1' } }
     )
-    expect(tags?.tag1?.length).toBeLessThan(600)
-    expect(tags?.tag1?.startsWith('yyyy')).toBe(true)
+    expect(tags?.tag1).toBe(`${'y'.repeat(512)}...`)
   })
 
   it('keeps a short mapped tag value intact', () => {

From 20f9277171f3058338bb6551aea6f1e9ba4ec3fc Mon Sep 17 00:00:00 2001
From: Waleed Latif <walif6@gmail.com>
Date: Mon, 21 Sep 2026 20:18:16 -0700
Subject: [PATCH 3/5] fix(knowledge): share the indexed-text bound, cut by code
 point, and reject oversized filenames and tags at the document APIs

---
 .../api/contracts/knowledge/documents.test.ts | 35 ++++++++++++
 .../lib/api/contracts/knowledge/documents.ts  | 54 ++++++++++++-------
 .../connectors/sync-persistence.test.ts       | 17 +++---
 .../knowledge/connectors/sync-persistence.ts  | 19 ++++---
 apps/sim/lib/knowledge/constants.ts           |  8 +++
 .../sim/lib/knowledge/upload-metadata.test.ts | 11 ++++
 apps/sim/lib/knowledge/upload-metadata.ts     |  6 ++-
 7 files changed, 114 insertions(+), 36 deletions(-)

diff --git a/apps/sim/lib/api/contracts/knowledge/documents.test.ts b/apps/sim/lib/api/contracts/knowledge/documents.test.ts
index 9a12967d460..e6a3a52fc5b 100644
--- a/apps/sim/lib/api/contracts/knowledge/documents.test.ts
+++ b/apps/sim/lib/api/contracts/knowledge/documents.test.ts
@@ -5,11 +5,14 @@ import { describe, expect, it } from 'vitest'
 import { z } from 'zod'
 import {
   bulkCreateDocumentsBodySchema,
+  createDocumentBodySchema,
   documentDataSchema,
   listKnowledgeDocumentsQuerySchema,
   parseDocumentTagFiltersParam,
+  updateDocumentBodySchema,
   upsertDocumentBodySchema,
 } from '@/lib/api/contracts/knowledge/documents'
+import { MAX_DOCUMENT_INDEXED_TEXT_LENGTH } from '@/lib/knowledge/constants'
 import { getDocumentIndexingStatus } from '@/lib/knowledge/documents/types'
 
 describe('document processing response compatibility', () => {
@@ -255,3 +258,35 @@ describe('internal document processingOptions', () => {
     })
   })
 })
+
+describe('document filename and tag bounds', () => {
+  const base = { fileUrl: 'https://example.com/a.txt', fileSize: 1, mimeType: 'text/plain' }
+  const atLimit = 'a'.repeat(MAX_DOCUMENT_INDEXED_TEXT_LENGTH)
+  const overLimit = `${atLimit}a`
+
+  it('accepts a filename and tag exactly at the indexed-text limit', () => {
+    expect(
+      createDocumentBodySchema.safeParse({ ...base, filename: atLimit, tag1: atLimit }).success
+    ).toBe(true)
+  })
+
+  it('rejects a filename over the limit on create, upsert, and update with a descriptive message', () => {
+    for (const schema of [createDocumentBodySchema, upsertDocumentBodySchema, updateDocumentBodySchema]) {
+      const result = schema.safeParse({ ...base, filename: overLimit })
+      expect(result.success).toBe(false)
+      expect(result.error?.issues[0]?.message).toBe(
+        `Filename cannot exceed ${MAX_DOCUMENT_INDEXED_TEXT_LENGTH} characters`
+      )
+    }
+  })
+
+  it('rejects a tag value over the limit on create and update', () => {
+    for (const schema of [createDocumentBodySchema, updateDocumentBodySchema]) {
+      const result = schema.safeParse({ ...base, filename: 'a.txt', tag3: overLimit })
+      expect(result.success).toBe(false)
+      expect(result.error?.issues[0]?.message).toBe(
+        `Tag values cannot exceed ${MAX_DOCUMENT_INDEXED_TEXT_LENGTH} characters`
+      )
+    }
+  })
+})
diff --git a/apps/sim/lib/api/contracts/knowledge/documents.ts b/apps/sim/lib/api/contracts/knowledge/documents.ts
index 4b586ff6765..3d8de902eeb 100644
--- a/apps/sim/lib/api/contracts/knowledge/documents.ts
+++ b/apps/sim/lib/api/contracts/knowledge/documents.ts
@@ -15,7 +15,11 @@ import {
 import { privateSecretProvenanceBundleSchema } from '@/lib/api/contracts/primitives'
 import { defineRouteContract } from '@/lib/api/contracts/types'
 import { PRIVATE_SECRET_PROVENANCE_FIELD } from '@/lib/execution/private-tool-metadata'
-import { getFieldTypeForSlot, MAX_KNOWLEDGE_DOCUMENTS_PER_CREATE } from '@/lib/knowledge/constants'
+import {
+  getFieldTypeForSlot,
+  MAX_DOCUMENT_INDEXED_TEXT_LENGTH,
+  MAX_KNOWLEDGE_DOCUMENTS_PER_CREATE,
+} from '@/lib/knowledge/constants'
 import { DOCUMENT_PROCESSING_STATUSES } from '@/lib/knowledge/documents/types'
 import { getOperatorsForFieldType, isValidFilterValue } from '@/lib/knowledge/filters/types'
 import { knowledgeDocumentUploadMetadataSchema } from '@/lib/knowledge/upload-metadata'
@@ -115,18 +119,26 @@ export function parseDocumentTagFiltersParam(
   return z.array(documentTagFilterSchema).parse(JSON.parse(value))
 }
 
+/** A text tag value that fits its index row; see {@link MAX_DOCUMENT_INDEXED_TEXT_LENGTH}. */
+const documentTagValueSchema = z
+  .string()
+  .max(MAX_DOCUMENT_INDEXED_TEXT_LENGTH, `Tag values cannot exceed ${MAX_DOCUMENT_INDEXED_TEXT_LENGTH} characters`)
+
 export const createDocumentBodySchema = z.object({
-  filename: z.string().min(1, 'Filename is required'),
+  filename: z
+    .string()
+    .min(1, 'Filename is required')
+    .max(MAX_DOCUMENT_INDEXED_TEXT_LENGTH, `Filename cannot exceed ${MAX_DOCUMENT_INDEXED_TEXT_LENGTH} characters`),
   fileUrl: knowledgeDocumentFileUrlSchema,
   fileSize: z.number().min(1, 'File size must be greater than 0'),
   mimeType: z.string().min(1, 'MIME type is required'),
-  tag1: z.string().optional(),
-  tag2: z.string().optional(),
-  tag3: z.string().optional(),
-  tag4: z.string().optional(),
-  tag5: z.string().optional(),
-  tag6: z.string().optional(),
-  tag7: z.string().optional(),
+  tag1: documentTagValueSchema.optional(),
+  tag2: documentTagValueSchema.optional(),
+  tag3: documentTagValueSchema.optional(),
+  tag4: documentTagValueSchema.optional(),
+  tag5: documentTagValueSchema.optional(),
+  tag6: documentTagValueSchema.optional(),
+  tag7: documentTagValueSchema.optional(),
   documentTagsData: z.string().optional(),
 })
 
@@ -165,7 +177,10 @@ export type SingleCreateDocumentBody = z.input<typeof singleCreateDocumentBodySc
 
 export const upsertDocumentBodySchema = z.object({
   documentId: z.string().optional(),
-  filename: z.string().min(1, 'Filename is required'),
+  filename: z
+    .string()
+    .min(1, 'Filename is required')
+    .max(MAX_DOCUMENT_INDEXED_TEXT_LENGTH, `Filename cannot exceed ${MAX_DOCUMENT_INDEXED_TEXT_LENGTH} characters`),
   fileUrl: knowledgeDocumentFileUrlSchema,
   fileSize: z.number().min(1, 'File size must be greater than 0'),
   mimeType: z.string().min(1, 'MIME type is required'),
@@ -196,7 +211,10 @@ export const bulkCreateDocumentsResponseSchema = z.object({
 })
 
 export const updateDocumentBodySchema = z.object({
-  filename: z.string().min(1, 'Filename is required').optional(),
+  filename: z
+    .string()
+    .min(1, 'Filename is required')
+    .max(MAX_DOCUMENT_INDEXED_TEXT_LENGTH, `Filename cannot exceed ${MAX_DOCUMENT_INDEXED_TEXT_LENGTH} characters`).optional(),
   enabled: z.boolean().optional(),
   chunkCount: z.number().min(0).optional(),
   tokenCount: z.number().min(0).optional(),
@@ -205,13 +223,13 @@ export const updateDocumentBodySchema = z.object({
   processingError: z.string().optional(),
   markFailedDueToTimeout: z.boolean().optional(),
   retryProcessing: z.boolean().optional(),
-  tag1: z.string().optional(),
-  tag2: z.string().optional(),
-  tag3: z.string().optional(),
-  tag4: z.string().optional(),
-  tag5: z.string().optional(),
-  tag6: z.string().optional(),
-  tag7: z.string().optional(),
+  tag1: documentTagValueSchema.optional(),
+  tag2: documentTagValueSchema.optional(),
+  tag3: documentTagValueSchema.optional(),
+  tag4: documentTagValueSchema.optional(),
+  tag5: documentTagValueSchema.optional(),
+  tag6: documentTagValueSchema.optional(),
+  tag7: documentTagValueSchema.optional(),
   number1: z.string().optional(),
   number2: z.string().optional(),
   number3: z.string().optional(),
diff --git a/apps/sim/lib/knowledge/connectors/sync-persistence.test.ts b/apps/sim/lib/knowledge/connectors/sync-persistence.test.ts
index 23a98dd5482..2089bb3ea9c 100644
--- a/apps/sim/lib/knowledge/connectors/sync-persistence.test.ts
+++ b/apps/sim/lib/knowledge/connectors/sync-persistence.test.ts
@@ -29,7 +29,9 @@ vi.mock('@/lib/knowledge/documents/storage-cleanup', () => ({
 }))
 vi.mock('@/connectors/registry.server', () => ({
   CONNECTOR_REGISTRY: {
-    fixture: { mapTags: (metadata: Record<string, unknown>) => ({ label: metadata.label }) },
+    fixture: {
+      mapTags: (metadata: Record<string, unknown>) => ({ label: metadata.label, owner: metadata.owner }),
+    },
   },
 }))
 
@@ -434,21 +436,22 @@ describe('organization source cache persistence', () => {
 })
 
 describe('resolveTagMapping', () => {
-  it('bounds a mapped tag value that would exceed its index row limit', () => {
+  it('bounds a mapped tag value that would exceed its index row limit and keeps a short one intact', () => {
     const tags = resolveTagMapping(
       'fixture',
-      { label: 'y'.repeat(5000) },
-      { tagSlotMapping: { label: 'tag1' } }
+      { label: 'y'.repeat(5000), owner: 'Purchasing' },
+      { tagSlotMapping: { label: 'tag1', owner: 'tag2' } }
     )
     expect(tags?.tag1).toBe(`${'y'.repeat(512)}...`)
+    expect(tags?.tag2).toBe('Purchasing')
   })
 
-  it('keeps a short mapped tag value intact', () => {
+  it('cuts by code point so a bounded value never ends in half a surrogate pair', () => {
     const tags = resolveTagMapping(
       'fixture',
-      { label: 'Purchasing' },
+      { label: '\u{1F600}'.repeat(600) },
       { tagSlotMapping: { label: 'tag1' } }
     )
-    expect(tags?.tag1).toBe('Purchasing')
+    expect(tags?.tag1).toBe(`${'\u{1F600}'.repeat(512)}...`)
   })
 })
diff --git a/apps/sim/lib/knowledge/connectors/sync-persistence.ts b/apps/sim/lib/knowledge/connectors/sync-persistence.ts
index 526861107bd..ef769c06e78 100644
--- a/apps/sim/lib/knowledge/connectors/sync-persistence.ts
+++ b/apps/sim/lib/knowledge/connectors/sync-persistence.ts
@@ -3,7 +3,6 @@ import { document, embedding, knowledgeBase, knowledgeConnector } from '@sim/db/
 import { createLogger } from '@sim/logger'
 import { chunkArray } from '@sim/utils/helpers'
 import { generateId } from '@sim/utils/id'
-import { truncate } from '@sim/utils/string'
 import { and, eq, exists, inArray, isNull, lt, or, sql } from 'drizzle-orm'
 import { getInternalApiBaseUrl } from '@/lib/core/utils/urls'
 import type { DbOrTx } from '@/lib/db/types'
@@ -27,6 +26,7 @@ import {
 } from '@/lib/knowledge/documents/storage-upload'
 import { buildStorageKeySegment } from '@/lib/uploads/core/storage-key'
 import { getFileMetadataByKeys } from '@/lib/uploads/server/metadata'
+import { MAX_DOCUMENT_INDEXED_TEXT_LENGTH } from '@/lib/knowledge/constants'
 import { CONNECTOR_REGISTRY } from '@/connectors/registry.server'
 import type { DocumentTags, ExternalDocument } from '@/connectors/types'
 
@@ -175,16 +175,15 @@ export async function persistDocumentAcls(
 const MAX_SAFE_TITLE_LENGTH = 200
 
 /**
- * A document's filename and text tags sit under btree indexes, and Postgres refuses an index
- * row past about 2.7 KB. A source title or tag value beyond that fails the row and, with it,
- * every sync that lists the document again. 512 characters keeps a four-byte-per-character
- * value inside the ceiling.
+ * Source titles and mapped tag values are untrusted machine input with no caller to refuse them,
+ * so they are cut to {@link MAX_DOCUMENT_INDEXED_TEXT_LENGTH} by code point, never inside a
+ * surrogate pair.
  */
-const MAX_INDEXED_TEXT_LENGTH = 512
-
-/** Bounds a source-supplied value that lands in an indexed text column. */
 function boundIndexedText(value: string): string {
-  return truncate(value, MAX_INDEXED_TEXT_LENGTH)
+  if (value.length <= MAX_DOCUMENT_INDEXED_TEXT_LENGTH) return value
+  const points = Array.from(value)
+  if (points.length <= MAX_DOCUMENT_INDEXED_TEXT_LENGTH) return value
+  return `${points.slice(0, MAX_DOCUMENT_INDEXED_TEXT_LENGTH).join('')}...`
 }
 
 function sanitizeStorageTitle(title: string): string {
@@ -265,7 +264,7 @@ export function resolveTagMapping(
   for (const [semanticKey, slot] of Object.entries(mapping)) {
     const value = semanticTags[semanticKey]
     ;(result as Record<string, unknown>)[slot] =
-      typeof value === 'string' ? boundIndexedText(value) : value != null ? value : null
+      typeof value === 'string' ? boundIndexedText(value) : (value ?? null)
   }
   return result
 }
diff --git a/apps/sim/lib/knowledge/constants.ts b/apps/sim/lib/knowledge/constants.ts
index b65aa6bd77f..f6de98cf0a0 100644
--- a/apps/sim/lib/knowledge/constants.ts
+++ b/apps/sim/lib/knowledge/constants.ts
@@ -3,6 +3,14 @@ import { MAX_FOLDERS_PER_WORKSPACE } from '@/lib/folders/constants'
 /** Max character length for a knowledge base description, enforced at every layer (UI, internal API, v1 API). */
 export const KNOWLEDGE_BASE_DESCRIPTION_MAX_LENGTH = 10_000
 
+/**
+ * Max character length for a document's filename and text tag values. Both sit under btree
+ * indexes, and Postgres refuses an index row past about 2.7 KB (SQLSTATE 54000); 512 characters
+ * keeps a four-byte-per-character value inside that ceiling. Connectors truncate source titles to
+ * it; the document APIs reject longer input.
+ */
+export const MAX_DOCUMENT_INDEXED_TEXT_LENGTH = 512
+
 /** Hard bound for path-indexed knowledge folder trees and recursive cascades. */
 export const MAX_KNOWLEDGE_FOLDERS_PER_WORKSPACE = MAX_FOLDERS_PER_WORKSPACE
 
diff --git a/apps/sim/lib/knowledge/upload-metadata.test.ts b/apps/sim/lib/knowledge/upload-metadata.test.ts
index 42cf71ed58c..c17dd77b3fe 100644
--- a/apps/sim/lib/knowledge/upload-metadata.test.ts
+++ b/apps/sim/lib/knowledge/upload-metadata.test.ts
@@ -7,8 +7,19 @@ import {
   knowledgeDocumentUploadMetadataSchema,
   persistedKnowledgeDocumentUploadMetadataSchema,
 } from '@/lib/knowledge/upload-metadata'
+import { MAX_DOCUMENT_INDEXED_TEXT_LENGTH } from '@/lib/knowledge/constants'
 
 describe('knowledgeDocumentUploadMetadataSchema', () => {
+  it('rejects a tag value that would not fit its index row', () => {
+    const result = knowledgeDocumentUploadMetadataSchema.safeParse({
+      tag1: 'a'.repeat(MAX_DOCUMENT_INDEXED_TEXT_LENGTH + 1),
+    })
+    expect(result.success).toBe(false)
+    expect(result.error?.issues[0]?.message).toBe(
+      `Knowledge document tag values cannot exceed ${MAX_DOCUMENT_INDEXED_TEXT_LENGTH} characters`
+    )
+  })
+
   it('rejects a recipe outside the accepted set', () => {
     const result = knowledgeDocumentUploadMetadataSchema.safeParse({
       processingOptions: { recipe: 'totally-bogus-recipe' },
diff --git a/apps/sim/lib/knowledge/upload-metadata.ts b/apps/sim/lib/knowledge/upload-metadata.ts
index 8b5c96c4ad9..6139e5464f1 100644
--- a/apps/sim/lib/knowledge/upload-metadata.ts
+++ b/apps/sim/lib/knowledge/upload-metadata.ts
@@ -1,5 +1,6 @@
 import { z } from 'zod'
 import type { RecursiveRecipe } from '@/lib/chunkers/types'
+import { MAX_DOCUMENT_INDEXED_TEXT_LENGTH } from '@/lib/knowledge/constants'
 
 /**
  * Recipes the recursive chunker implements. Mirrors `RecursiveRecipe`; the
@@ -35,7 +36,10 @@ const LANGUAGE_TAG_SHAPE = /^[A-Za-z]{2,8}(?:-[A-Za-z0-9]{1,8})*$/
 
 const knowledgeDocumentUploadTagSchema = z
   .string()
-  .max(1000, 'Knowledge document tag values cannot exceed 1000 characters')
+  .max(
+    MAX_DOCUMENT_INDEXED_TEXT_LENGTH,
+    `Knowledge document tag values cannot exceed ${MAX_DOCUMENT_INDEXED_TEXT_LENGTH} characters`
+  )
   .optional()
 
 const knowledgeDocumentUploadTagShape = {

From d187644c5af5cbb6d88356b8e75270de2d7e92e8 Mon Sep 17 00:00:00 2001
From: Waleed Latif <walif6@gmail.com>
Date: Mon, 21 Sep 2026 20:25:51 -0700
Subject: [PATCH 4/5] fix(knowledge): cut bounded text with a shared
 surrogate-safe helper inside the limit and leave stored upload metadata
 untouched

---
 .../api/contracts/knowledge/documents.test.ts |  6 +++++-
 .../lib/api/contracts/knowledge/documents.ts  | 21 +++++++++++++++----
 .../connectors/sync-persistence.test.ts       | 13 ++++++++----
 .../knowledge/connectors/sync-persistence.ts  | 19 ++++++++++-------
 .../sim/lib/knowledge/upload-metadata.test.ts | 11 ----------
 apps/sim/lib/knowledge/upload-metadata.ts     |  6 +-----
 packages/utils/src/string.test.ts             | 17 +++++++++++++++
 packages/utils/src/string.ts                  | 15 +++++++++++++
 8 files changed, 76 insertions(+), 32 deletions(-)

diff --git a/apps/sim/lib/api/contracts/knowledge/documents.test.ts b/apps/sim/lib/api/contracts/knowledge/documents.test.ts
index e6a3a52fc5b..3bbc3bc7c09 100644
--- a/apps/sim/lib/api/contracts/knowledge/documents.test.ts
+++ b/apps/sim/lib/api/contracts/knowledge/documents.test.ts
@@ -271,7 +271,11 @@ describe('document filename and tag bounds', () => {
   })
 
   it('rejects a filename over the limit on create, upsert, and update with a descriptive message', () => {
-    for (const schema of [createDocumentBodySchema, upsertDocumentBodySchema, updateDocumentBodySchema]) {
+    for (const schema of [
+      createDocumentBodySchema,
+      upsertDocumentBodySchema,
+      updateDocumentBodySchema,
+    ]) {
       const result = schema.safeParse({ ...base, filename: overLimit })
       expect(result.success).toBe(false)
       expect(result.error?.issues[0]?.message).toBe(
diff --git a/apps/sim/lib/api/contracts/knowledge/documents.ts b/apps/sim/lib/api/contracts/knowledge/documents.ts
index 3d8de902eeb..cf61931c859 100644
--- a/apps/sim/lib/api/contracts/knowledge/documents.ts
+++ b/apps/sim/lib/api/contracts/knowledge/documents.ts
@@ -122,13 +122,19 @@ export function parseDocumentTagFiltersParam(
 /** A text tag value that fits its index row; see {@link MAX_DOCUMENT_INDEXED_TEXT_LENGTH}. */
 const documentTagValueSchema = z
   .string()
-  .max(MAX_DOCUMENT_INDEXED_TEXT_LENGTH, `Tag values cannot exceed ${MAX_DOCUMENT_INDEXED_TEXT_LENGTH} characters`)
+  .max(
+    MAX_DOCUMENT_INDEXED_TEXT_LENGTH,
+    `Tag values cannot exceed ${MAX_DOCUMENT_INDEXED_TEXT_LENGTH} characters`
+  )
 
 export const createDocumentBodySchema = z.object({
   filename: z
     .string()
     .min(1, 'Filename is required')
-    .max(MAX_DOCUMENT_INDEXED_TEXT_LENGTH, `Filename cannot exceed ${MAX_DOCUMENT_INDEXED_TEXT_LENGTH} characters`),
+    .max(
+      MAX_DOCUMENT_INDEXED_TEXT_LENGTH,
+      `Filename cannot exceed ${MAX_DOCUMENT_INDEXED_TEXT_LENGTH} characters`
+    ),
   fileUrl: knowledgeDocumentFileUrlSchema,
   fileSize: z.number().min(1, 'File size must be greater than 0'),
   mimeType: z.string().min(1, 'MIME type is required'),
@@ -180,7 +186,10 @@ export const upsertDocumentBodySchema = z.object({
   filename: z
     .string()
     .min(1, 'Filename is required')
-    .max(MAX_DOCUMENT_INDEXED_TEXT_LENGTH, `Filename cannot exceed ${MAX_DOCUMENT_INDEXED_TEXT_LENGTH} characters`),
+    .max(
+      MAX_DOCUMENT_INDEXED_TEXT_LENGTH,
+      `Filename cannot exceed ${MAX_DOCUMENT_INDEXED_TEXT_LENGTH} characters`
+    ),
   fileUrl: knowledgeDocumentFileUrlSchema,
   fileSize: z.number().min(1, 'File size must be greater than 0'),
   mimeType: z.string().min(1, 'MIME type is required'),
@@ -214,7 +223,11 @@ export const updateDocumentBodySchema = z.object({
   filename: z
     .string()
     .min(1, 'Filename is required')
-    .max(MAX_DOCUMENT_INDEXED_TEXT_LENGTH, `Filename cannot exceed ${MAX_DOCUMENT_INDEXED_TEXT_LENGTH} characters`).optional(),
+    .max(
+      MAX_DOCUMENT_INDEXED_TEXT_LENGTH,
+      `Filename cannot exceed ${MAX_DOCUMENT_INDEXED_TEXT_LENGTH} characters`
+    )
+    .optional(),
   enabled: z.boolean().optional(),
   chunkCount: z.number().min(0).optional(),
   tokenCount: z.number().min(0).optional(),
diff --git a/apps/sim/lib/knowledge/connectors/sync-persistence.test.ts b/apps/sim/lib/knowledge/connectors/sync-persistence.test.ts
index 2089bb3ea9c..ae29b4aabc7 100644
--- a/apps/sim/lib/knowledge/connectors/sync-persistence.test.ts
+++ b/apps/sim/lib/knowledge/connectors/sync-persistence.test.ts
@@ -30,7 +30,10 @@ vi.mock('@/lib/knowledge/documents/storage-cleanup', () => ({
 vi.mock('@/connectors/registry.server', () => ({
   CONNECTOR_REGISTRY: {
     fixture: {
-      mapTags: (metadata: Record<string, unknown>) => ({ label: metadata.label, owner: metadata.owner }),
+      mapTags: (metadata: Record<string, unknown>) => ({
+        label: metadata.label,
+        owner: metadata.owner,
+      }),
     },
   },
 }))
@@ -366,7 +369,8 @@ describe('persistSourceDocumentFailures', () => {
       priorByExternalId: new Map(),
     })
     const [rows] = dbChainMockFns.values.mock.calls[0] as [Array<{ filename: string }>]
-    expect(rows[0].filename).toBe(`${'x'.repeat(512)}...`)
+    expect(rows[0].filename).toBe(`${'x'.repeat(509)}...`)
+    expect(rows[0].filename.length).toBe(512)
   })
   it('refuses to commit a failure under a reclaimed lease', async () => {
     queueTableRows(schemaMock.knowledgeBase, [{ id: 'kb' }])
@@ -442,7 +446,7 @@ describe('resolveTagMapping', () => {
       { label: 'y'.repeat(5000), owner: 'Purchasing' },
       { tagSlotMapping: { label: 'tag1', owner: 'tag2' } }
     )
-    expect(tags?.tag1).toBe(`${'y'.repeat(512)}...`)
+    expect(tags?.tag1).toBe(`${'y'.repeat(509)}...`)
     expect(tags?.tag2).toBe('Purchasing')
   })
 
@@ -452,6 +456,7 @@ describe('resolveTagMapping', () => {
       { label: '\u{1F600}'.repeat(600) },
       { tagSlotMapping: { label: 'tag1' } }
     )
-    expect(tags?.tag1).toBe(`${'\u{1F600}'.repeat(512)}...`)
+    expect(tags?.tag1).toBe(`${'\u{1F600}'.repeat(254)}...`)
+    expect(tags?.tag1?.length).toBeLessThanOrEqual(512)
   })
 })
diff --git a/apps/sim/lib/knowledge/connectors/sync-persistence.ts b/apps/sim/lib/knowledge/connectors/sync-persistence.ts
index ef769c06e78..b5d2e8a221f 100644
--- a/apps/sim/lib/knowledge/connectors/sync-persistence.ts
+++ b/apps/sim/lib/knowledge/connectors/sync-persistence.ts
@@ -3,6 +3,7 @@ import { document, embedding, knowledgeBase, knowledgeConnector } from '@sim/db/
 import { createLogger } from '@sim/logger'
 import { chunkArray } from '@sim/utils/helpers'
 import { generateId } from '@sim/utils/id'
+import { truncateAtCodePoint } from '@sim/utils/string'
 import { and, eq, exists, inArray, isNull, lt, or, sql } from 'drizzle-orm'
 import { getInternalApiBaseUrl } from '@/lib/core/utils/urls'
 import type { DbOrTx } from '@/lib/db/types'
@@ -18,6 +19,7 @@ import type { ConnectorFailureDiagnostic } from '@/lib/knowledge/connectors/conn
 import { resolveSourceModifiedAt } from '@/lib/knowledge/connectors/source-modified-at'
 import { SOURCE_CONTENT_ERROR } from '@/lib/knowledge/connectors/sync-limits'
 import { assertSyncLeaseHeldInTx, type SyncWriteLease } from '@/lib/knowledge/connectors/sync-lock'
+import { MAX_DOCUMENT_INDEXED_TEXT_LENGTH } from '@/lib/knowledge/constants'
 import type { DocumentData } from '@/lib/knowledge/documents/service'
 import { enqueueKnowledgeStorageCleanup } from '@/lib/knowledge/documents/storage-cleanup'
 import {
@@ -26,7 +28,6 @@ import {
 } from '@/lib/knowledge/documents/storage-upload'
 import { buildStorageKeySegment } from '@/lib/uploads/core/storage-key'
 import { getFileMetadataByKeys } from '@/lib/uploads/server/metadata'
-import { MAX_DOCUMENT_INDEXED_TEXT_LENGTH } from '@/lib/knowledge/constants'
 import { CONNECTOR_REGISTRY } from '@/connectors/registry.server'
 import type { DocumentTags, ExternalDocument } from '@/connectors/types'
 
@@ -174,16 +175,20 @@ export async function persistDocumentAcls(
 
 const MAX_SAFE_TITLE_LENGTH = 200
 
+/** The suffix a cut value carries, counted inside {@link MAX_DOCUMENT_INDEXED_TEXT_LENGTH}. */
+const INDEXED_TEXT_CUT_SUFFIX = '...'
+
 /**
  * Source titles and mapped tag values are untrusted machine input with no caller to refuse them,
- * so they are cut to {@link MAX_DOCUMENT_INDEXED_TEXT_LENGTH} by code point, never inside a
- * surrogate pair.
+ * so they are cut to {@link MAX_DOCUMENT_INDEXED_TEXT_LENGTH} code units, suffix included, and
+ * never inside a surrogate pair. The result always passes the document APIs' own bound.
  */
 function boundIndexedText(value: string): string {
-  if (value.length <= MAX_DOCUMENT_INDEXED_TEXT_LENGTH) return value
-  const points = Array.from(value)
-  if (points.length <= MAX_DOCUMENT_INDEXED_TEXT_LENGTH) return value
-  return `${points.slice(0, MAX_DOCUMENT_INDEXED_TEXT_LENGTH).join('')}...`
+  return truncateAtCodePoint(
+    value,
+    MAX_DOCUMENT_INDEXED_TEXT_LENGTH - INDEXED_TEXT_CUT_SUFFIX.length,
+    INDEXED_TEXT_CUT_SUFFIX
+  )
 }
 
 function sanitizeStorageTitle(title: string): string {
diff --git a/apps/sim/lib/knowledge/upload-metadata.test.ts b/apps/sim/lib/knowledge/upload-metadata.test.ts
index c17dd77b3fe..42cf71ed58c 100644
--- a/apps/sim/lib/knowledge/upload-metadata.test.ts
+++ b/apps/sim/lib/knowledge/upload-metadata.test.ts
@@ -7,19 +7,8 @@ import {
   knowledgeDocumentUploadMetadataSchema,
   persistedKnowledgeDocumentUploadMetadataSchema,
 } from '@/lib/knowledge/upload-metadata'
-import { MAX_DOCUMENT_INDEXED_TEXT_LENGTH } from '@/lib/knowledge/constants'
 
 describe('knowledgeDocumentUploadMetadataSchema', () => {
-  it('rejects a tag value that would not fit its index row', () => {
-    const result = knowledgeDocumentUploadMetadataSchema.safeParse({
-      tag1: 'a'.repeat(MAX_DOCUMENT_INDEXED_TEXT_LENGTH + 1),
-    })
-    expect(result.success).toBe(false)
-    expect(result.error?.issues[0]?.message).toBe(
-      `Knowledge document tag values cannot exceed ${MAX_DOCUMENT_INDEXED_TEXT_LENGTH} characters`
-    )
-  })
-
   it('rejects a recipe outside the accepted set', () => {
     const result = knowledgeDocumentUploadMetadataSchema.safeParse({
       processingOptions: { recipe: 'totally-bogus-recipe' },
diff --git a/apps/sim/lib/knowledge/upload-metadata.ts b/apps/sim/lib/knowledge/upload-metadata.ts
index 6139e5464f1..8b5c96c4ad9 100644
--- a/apps/sim/lib/knowledge/upload-metadata.ts
+++ b/apps/sim/lib/knowledge/upload-metadata.ts
@@ -1,6 +1,5 @@
 import { z } from 'zod'
 import type { RecursiveRecipe } from '@/lib/chunkers/types'
-import { MAX_DOCUMENT_INDEXED_TEXT_LENGTH } from '@/lib/knowledge/constants'
 
 /**
  * Recipes the recursive chunker implements. Mirrors `RecursiveRecipe`; the
@@ -36,10 +35,7 @@ const LANGUAGE_TAG_SHAPE = /^[A-Za-z]{2,8}(?:-[A-Za-z0-9]{1,8})*$/
 
 const knowledgeDocumentUploadTagSchema = z
   .string()
-  .max(
-    MAX_DOCUMENT_INDEXED_TEXT_LENGTH,
-    `Knowledge document tag values cannot exceed ${MAX_DOCUMENT_INDEXED_TEXT_LENGTH} characters`
-  )
+  .max(1000, 'Knowledge document tag values cannot exceed 1000 characters')
   .optional()
 
 const knowledgeDocumentUploadTagShape = {
diff --git a/packages/utils/src/string.test.ts b/packages/utils/src/string.test.ts
index 1a33db3ce04..b817c2fff8b 100644
--- a/packages/utils/src/string.test.ts
+++ b/packages/utils/src/string.test.ts
@@ -16,6 +16,7 @@ import {
   slugify,
   stripVersionSuffix,
   truncate,
+  truncateAtCodePoint,
 } from './string.js'
 
 describe('slugify', () => {
@@ -304,3 +305,19 @@ describe('hasRegexMetacharacter', () => {
     }
   })
 })
+
+describe('truncateAtCodePoint', () => {
+  it('returns the input untouched when it fits', () => {
+    expect(truncateAtCodePoint('ab😀cd', 10)).toBe('ab😀cd')
+  })
+
+  it('cuts like truncate when the cut lands between code points', () => {
+    expect(truncateAtCodePoint('ab😀cd', 4)).toBe('ab😀...')
+    expect(truncateAtCodePoint('hello world', 8, ' …')).toBe('hello wo …')
+  })
+
+  it('moves the cut back one unit rather than splitting a surrogate pair', () => {
+    expect(truncateAtCodePoint('ab😀cd', 3)).toBe('ab...')
+    expect(truncateAtCodePoint('😀'.repeat(3), 3)).toBe('😀...')
+  })
+})
diff --git a/packages/utils/src/string.ts b/packages/utils/src/string.ts
index 5518821940f..8cf8dbb5c33 100644
--- a/packages/utils/src/string.ts
+++ b/packages/utils/src/string.ts
@@ -33,6 +33,21 @@ export function truncate(str: string, sliceLength: number, suffix = '...'): stri
   return str.length > sliceLength ? str.slice(0, sliceLength) + suffix : str
 }
 
+/**
+ * Like {@link truncate}, but never cuts inside a surrogate pair: when the code unit at the cut
+ * would split an astral character, the cut moves one unit earlier. Lengths are still counted in
+ * UTF-16 code units, so the result of a cut is at most `sliceLength + suffix.length` units.
+ *
+ * @example
+ * truncateAtCodePoint('ab😀cd', 3)   // 'ab...' (the cut at 3 would split the emoji)
+ * truncateAtCodePoint('ab😀cd', 4)   // 'ab😀...'
+ */
+export function truncateAtCodePoint(str: string, sliceLength: number, suffix = '...'): string {
+  if (str.length <= sliceLength) return str
+  const splitsPair = sliceLength > 0 && (str.charCodeAt(sliceLength - 1) & 0xfc00) === 0xd800
+  return str.slice(0, splitsPair ? sliceLength - 1 : sliceLength) + suffix
+}
+
 /**
  * Lowercases `value` into the `[a-z0-9-]` charset: every run of other characters
  * becomes one hyphen, and leading and trailing hyphens are dropped.

From 95960d552ab04261f48325ddd0d31a17519944e5 Mon Sep 17 00:00:00 2001
From: Waleed Latif <walif6@gmail.com>
Date: Mon, 21 Sep 2026 20:35:14 -0700
Subject: [PATCH 5/5] fix(knowledge): leave values at the limit untouched and
 refuse over-long tag values on the tag-data and tag-update paths

---
 apps/sim/lib/knowledge/application/documents.ts   |  6 ++++--
 .../knowledge/connectors/sync-persistence.test.ts | 10 ++++++++++
 .../lib/knowledge/connectors/sync-persistence.ts  |  1 +
 apps/sim/lib/knowledge/documents/service.ts       |  5 ++++-
 apps/sim/lib/knowledge/tags/utils.test.ts         | 15 ++++++++++++++-
 apps/sim/lib/knowledge/tags/utils.ts              | 12 ++++++++++++
 6 files changed, 45 insertions(+), 4 deletions(-)

diff --git a/apps/sim/lib/knowledge/application/documents.ts b/apps/sim/lib/knowledge/application/documents.ts
index dc584acb7ac..036aa97aea2 100644
--- a/apps/sim/lib/knowledge/application/documents.ts
+++ b/apps/sim/lib/knowledge/application/documents.ts
@@ -68,7 +68,7 @@ import {
   toKnowledgeTagFilterConditions,
 } from '@/lib/knowledge/tags/filter-resolution'
 import { getDocumentTagDefinitions } from '@/lib/knowledge/tags/service'
-import { validateTagValue } from '@/lib/knowledge/tags/utils'
+import { validateTagValue, validateTagValueLength } from '@/lib/knowledge/tags/utils'
 import { StorageService } from '@/lib/uploads'
 import { generateKnowledgeBaseFileKey } from '@/lib/uploads/contexts/knowledge-base/knowledge-base-file-manager'
 import { recordKnowledgeBaseFileOwnership } from '@/lib/uploads/server/metadata'
@@ -252,7 +252,9 @@ async function resolveKnowledgeDocumentTagValueUpdates(
         `Tag "${definition.displayName}" requires a value; use null to clear it`
       )
     }
-    const validationError = validateTagValue(definition.displayName, value, definition.fieldType)
+    const validationError =
+      validateTagValueLength(definition.displayName, value) ??
+      validateTagValue(definition.displayName, value, definition.fieldType)
     if (validationError) {
       throw new OrchestrationError('validation', validationError)
     }
diff --git a/apps/sim/lib/knowledge/connectors/sync-persistence.test.ts b/apps/sim/lib/knowledge/connectors/sync-persistence.test.ts
index ae29b4aabc7..fd90b59c1d4 100644
--- a/apps/sim/lib/knowledge/connectors/sync-persistence.test.ts
+++ b/apps/sim/lib/knowledge/connectors/sync-persistence.test.ts
@@ -450,6 +450,16 @@ describe('resolveTagMapping', () => {
     expect(tags?.tag2).toBe('Purchasing')
   })
 
+  it('keeps a value exactly at the limit untouched', () => {
+    const atLimit = 'z'.repeat(512)
+    const tags = resolveTagMapping(
+      'fixture',
+      { label: atLimit },
+      { tagSlotMapping: { label: 'tag1' } }
+    )
+    expect(tags?.tag1).toBe(atLimit)
+  })
+
   it('cuts by code point so a bounded value never ends in half a surrogate pair', () => {
     const tags = resolveTagMapping(
       'fixture',
diff --git a/apps/sim/lib/knowledge/connectors/sync-persistence.ts b/apps/sim/lib/knowledge/connectors/sync-persistence.ts
index b5d2e8a221f..48946ea7067 100644
--- a/apps/sim/lib/knowledge/connectors/sync-persistence.ts
+++ b/apps/sim/lib/knowledge/connectors/sync-persistence.ts
@@ -184,6 +184,7 @@ const INDEXED_TEXT_CUT_SUFFIX = '...'
  * never inside a surrogate pair. The result always passes the document APIs' own bound.
  */
 function boundIndexedText(value: string): string {
+  if (value.length <= MAX_DOCUMENT_INDEXED_TEXT_LENGTH) return value
   return truncateAtCodePoint(
     value,
     MAX_DOCUMENT_INDEXED_TEXT_LENGTH - INDEXED_TEXT_CUT_SUFFIX.length,
diff --git a/apps/sim/lib/knowledge/documents/service.ts b/apps/sim/lib/knowledge/documents/service.ts
index 3d6820369cf..36732b8e036 100644
--- a/apps/sim/lib/knowledge/documents/service.ts
+++ b/apps/sim/lib/knowledge/documents/service.ts
@@ -179,6 +179,7 @@ import {
   parseNumberValue,
   uncompilableTagFilterError,
   validateTagValue,
+  validateTagValueLength,
 } from '@/lib/knowledge/tags/utils'
 import type { ProcessedDocumentTags } from '@/lib/knowledge/types'
 import { embeddingVectorValues } from '@/lib/knowledge/vector-columns'
@@ -552,7 +553,9 @@ function resolveDocumentTags(
 
     const rawValue = typeof tag.value === 'string' ? tag.value.trim() : tag.value
     const actualFieldType = existingDef.fieldType || fieldType
-    const validationError = validateTagValue(tagName, String(rawValue), actualFieldType)
+    const validationError =
+      validateTagValueLength(tagName, String(rawValue)) ??
+      validateTagValue(tagName, String(rawValue), actualFieldType)
     if (validationError) {
       typeErrors.push(validationError)
     }
diff --git a/apps/sim/lib/knowledge/tags/utils.test.ts b/apps/sim/lib/knowledge/tags/utils.test.ts
index d99b080eecc..078e7c563d6 100644
--- a/apps/sim/lib/knowledge/tags/utils.test.ts
+++ b/apps/sim/lib/knowledge/tags/utils.test.ts
@@ -2,7 +2,11 @@
  * @vitest-environment node
  */
 import { describe, expect, it } from 'vitest'
-import { coerceTagFilterValue, validateTagValue } from '@/lib/knowledge/tags/utils'
+import {
+  coerceTagFilterValue,
+  validateTagValue,
+  validateTagValueLength,
+} from '@/lib/knowledge/tags/utils'
 
 describe('coerceTagFilterValue', () => {
   it('accepts exactly what validateTagValue accepts', () => {
@@ -68,3 +72,12 @@ describe('validateTagValue', () => {
     expect(validateTagValue('name', 'anything', 'json')).toBeNull()
   })
 })
+
+describe('validateTagValueLength', () => {
+  it('accepts a value at the indexed-text limit and names the tag past it', () => {
+    expect(validateTagValueLength('Labels', 'a'.repeat(512))).toBeNull()
+    expect(validateTagValueLength('Labels', 'a'.repeat(513))).toBe(
+      'Tag "Labels" cannot exceed 512 characters'
+    )
+  })
+})
diff --git a/apps/sim/lib/knowledge/tags/utils.ts b/apps/sim/lib/knowledge/tags/utils.ts
index 1d00da28889..4cd7ec4b869 100644
--- a/apps/sim/lib/knowledge/tags/utils.ts
+++ b/apps/sim/lib/knowledge/tags/utils.ts
@@ -1,4 +1,5 @@
 import { OrchestrationError } from '@/lib/core/orchestration/types'
+import { MAX_DOCUMENT_INDEXED_TEXT_LENGTH } from '@/lib/knowledge/constants'
 
 const DATE_ONLY_PATTERN = /^\d{4}-\d{2}-\d{2}$/
 
@@ -94,6 +95,17 @@ export function uncompilableTagFilterError(filter: {
  * Validate a tag value against its expected field type
  * Returns an error message if invalid, or null if valid
  */
+/**
+ * Text tag values sit under an index whose rows Postgres caps in size; a value past
+ * {@link MAX_DOCUMENT_INDEXED_TEXT_LENGTH} would fail the document write itself, so it is
+ * refused with a message naming the tag instead.
+ */
+export function validateTagValueLength(tagName: string, value: string): string | null {
+  return value.length > MAX_DOCUMENT_INDEXED_TEXT_LENGTH
+    ? `Tag "${tagName}" cannot exceed ${MAX_DOCUMENT_INDEXED_TEXT_LENGTH} characters`
+    : null
+}
+
 export function validateTagValue(tagName: string, value: string, fieldType: string): string | null {
   if (fieldType !== 'boolean' && fieldType !== 'number' && fieldType !== 'date') return null