simstudioai · waleedlatif1 · Aug 15, 2026 · Aug 15, 2026 · Aug 15, 2026
diff --git a/.../app/workspace/[workspaceId]/knowledge/components/create-base-modal/create-base-modal.tsx b/.../app/workspace/[workspaceId]/knowledge/components/create-base-modal/create-base-modal.tsx
@@ -25,6 +25,7 @@ import { getErrorMessage } from '@sim/utils/errors'
 import { useParams } from 'next/navigation'
 import { type FieldErrors, useForm } from 'react-hook-form'
 import { z } from 'zod'
+import { MAX_CHUNKING_SEPARATOR_LENGTH, MAX_CHUNKING_SEPARATORS } from '@/lib/chunkers/constants'
 import type { StrategyOptions } from '@/lib/chunkers/types'
 import { KNOWLEDGE_BASE_DESCRIPTION_MAX_LENGTH } from '@/lib/knowledge/constants'
 import {
@@ -57,6 +58,14 @@ const STRATEGY_OPTIONS = [
   { value: 'regex', label: 'Regex (custom pattern)' },
 ] as const
 
+/** Splits the comma-separated separator field into the list the API receives. */
+function parseSeparators(value: string | undefined): string[] {
+  if (!value?.trim()) return []
+  return value
+    .split(',')
+    .map((separator) => separator.trim().replace(/\\n/g, '\n').replace(/\\t/g, '\t'))
+}
+
 const STRATEGY_COMBOBOX_OPTIONS: ComboboxOption[] = STRATEGY_OPTIONS.map((o) => ({
   label: o.label,
   value: o.value,
@@ -124,6 +133,31 @@ const FormSchema = z
       path: ['regexPattern'],
     }
   )
+  /**
+   * Gated on the strategy for the same reason the regex pattern is: the field only
+   * renders for `recursive` and only that strategy submits it, so an out-of-bound
+   * value left behind by a strategy switch must not block a submit that drops it.
+   */
+  .refine(
+    (data) =>
+      data.strategy !== 'recursive' ||
+      parseSeparators(data.customSeparators).length <= MAX_CHUNKING_SEPARATORS,
+    {
+      message: `At most ${MAX_CHUNKING_SEPARATORS} separators are allowed`,
+      path: ['customSeparators'],
+    }
+  )
+  .refine(
+    (data) =>
+      data.strategy !== 'recursive' ||
+      parseSeparators(data.customSeparators).every(
+        (separator) => separator.length <= MAX_CHUNKING_SEPARATOR_LENGTH
+      ),
+    {
+      message: `Each separator must be ${MAX_CHUNKING_SEPARATOR_LENGTH} characters or less`,
+      path: ['customSeparators'],
+    }
+  )
 
 type FormInputValues = z.input<typeof FormSchema>
 type FormValues = z.output<typeof FormSchema>
@@ -265,11 +299,7 @@ export const CreateBaseModal = memo(function CreateBaseModal({
               ...(data.regexStrictBoundaries && { strictBoundaries: true }),
             }
           : data.strategy === 'recursive' && data.customSeparators?.trim()
-            ? {
-                separators: data.customSeparators
-                  .split(',')
-                  .map((s) => s.trim().replace(/\\n/g, '\n').replace(/\\t/g, '\t')),
-              }
+            ? { separators: parseSeparators(data.customSeparators) }
             : undefined
 
       const newKnowledgeBase = await createKnowledgeBaseMutation.mutateAsync({
@@ -465,11 +495,13 @@ export const CreateBaseModal = memo(function CreateBaseModal({
             <ChipModalField
               type='custom'
               title='Custom Separators (optional)'
-              hint='Comma-separated list of delimiters in priority order. Leave empty for default separators.'
+              hint={`Comma-separated list of delimiters in priority order, up to ${MAX_CHUNKING_SEPARATORS}. Leave empty for default separators.`}
+              error={errors.customSeparators?.message}
             >
               <ChipInput
                 placeholder='e.g. \n\n, \n, . ,  '
                 {...register('customSeparators')}
+                error={Boolean(errors.customSeparators)}
                 autoComplete='off'
                 data-form-type='other'
               />

diff --git a/apps/sim/lib/api/contracts/knowledge/base.test.ts b/apps/sim/lib/api/contracts/knowledge/base.test.ts
@@ -0,0 +1,77 @@
+/**
+ * @vitest-environment node
+ */
+import { describe, expect, it } from 'vitest'
+import {
+  chunkingStrategyOptionsSchema,
+  createKnowledgeBaseBodySchema,
+  knowledgeBaseDataSchema,
+} from '@/lib/api/contracts/knowledge/base'
+import { MAX_CHUNKING_SEPARATOR_LENGTH, MAX_CHUNKING_SEPARATORS } from '@/lib/chunkers/constants'
+
+const separators = (count: number) => Array.from({ length: count }, (_, i) => `@@sep${i}@@`)
+
+describe('chunkingStrategyOptionsSchema.separators', () => {
+  it('accepts a separator list at the bound', () => {
+    const parsed = chunkingStrategyOptionsSchema.parse({
+      separators: separators(MAX_CHUNKING_SEPARATORS),
+    })
+    expect(parsed.separators).toHaveLength(MAX_CHUNKING_SEPARATORS)
+  })
+
+  it('rejects more separators than the bound', () => {
+    const result = chunkingStrategyOptionsSchema.safeParse({
+      separators: separators(MAX_CHUNKING_SEPARATORS + 1),
+    })
+    expect(result.success).toBe(false)
+  })
+
+  it('rejects a separator longer than the per-item bound', () => {
+    const result = chunkingStrategyOptionsSchema.safeParse({
+      separators: ['|'.repeat(MAX_CHUNKING_SEPARATOR_LENGTH + 1)],
+    })
+    expect(result.success).toBe(false)
+  })
+
+  it('rejects an oversized list on the knowledge base create body', () => {
+    const result = createKnowledgeBaseBodySchema.safeParse({
+      name: 'kb',
+      workspaceId: 'ws',
+      chunkingConfig: {
+        maxSize: 1024,
+        minSize: 100,
+        overlap: 200,
+        strategy: 'recursive',
+        strategyOptions: { separators: separators(5000) },
+      },
+    })
+    expect(result.success).toBe(false)
+  })
+})
+
+describe('knowledgeBaseDataSchema.chunkingConfig', () => {
+  it('still reads a stored config written before the separator bound', () => {
+    const result = knowledgeBaseDataSchema.safeParse({
+      id: 'kb-1',
+      userId: 'u-1',
+      name: 'kb',
+      description: null,
+      tokenCount: 0,
+      embeddingModel: 'text-embedding-3-small',
+      embeddingDimension: 1536,
+      chunkingConfig: {
+        maxSize: 1024,
+        minSize: 100,
+        overlap: 200,
+        strategy: 'recursive',
+        strategyOptions: { separators: separators(5000) },
+      },
+      createdAt: new Date().toISOString(),
+      updatedAt: new Date().toISOString(),
+      deletedAt: null,
+      workspaceId: 'ws',
+      folderId: null,
+    })
+    expect(result.success).toBe(true)
+  })
+})
diff --git a/apps/sim/lib/api/contracts/knowledge/base.ts b/apps/sim/lib/api/contracts/knowledge/base.ts
@@ -6,6 +6,7 @@ import {
   wireDateSchema,
 } from '@/lib/api/contracts/knowledge/shared'
 import { defineRouteContract } from '@/lib/api/contracts/types'
+import { MAX_CHUNKING_SEPARATOR_LENGTH, MAX_CHUNKING_SEPARATORS } from '@/lib/chunkers/constants'
 import type { StrategyOptions } from '@/lib/chunkers/types'
 import {
   DEFAULT_CHUNKING_CONFIG,
@@ -20,7 +21,13 @@ export const listKnowledgeBasesQuerySchema = z.object({
   scope: knowledgeScopeSchema.default('active'),
 })
 
-export const chunkingStrategyOptionsSchema = z
+/**
+ * Strategy options as they are stored. Reads stay tolerant of a `separators`
+ * list written before {@link chunkingStrategyOptionsSchema} bounded it, so an
+ * oversized legacy config lists instead of failing response validation. The
+ * chunker clamps such a list at construction, so nothing reprocesses unbounded.
+ */
+export const storedChunkingStrategyOptionsSchema = z
   .object({
     pattern: z
       .string()
@@ -42,6 +49,29 @@ export const chunkingStrategyOptionsSchema = z
   })
   .strict() satisfies z.ZodType<StrategyOptions>
 
+/**
+ * Strategy options accepted on writes. `separators` is bounded in both length
+ * and item size: the recursive chunker rescans the whole document once per
+ * separator, synchronously, so an unbounded list turns one persisted config
+ * into seconds of uninterruptible CPU on every later document upload.
+ */
+export const chunkingStrategyOptionsSchema = storedChunkingStrategyOptionsSchema
+  .extend({
+    separators: z
+      .array(
+        z
+          .string()
+          .max(
+            MAX_CHUNKING_SEPARATOR_LENGTH,
+            `Each separator must be ${MAX_CHUNKING_SEPARATOR_LENGTH} characters or less`
+          )
+      )
+      .max(MAX_CHUNKING_SEPARATORS, `At most ${MAX_CHUNKING_SEPARATORS} separators are allowed`)
+      .optional()
+      .describe('Ordered separators used to split content into chunks.'),
+  })
+  .strict() satisfies z.ZodType<StrategyOptions>
+
 export const chunkingConfigSchema = z
   .object({
     maxSize: z.number().min(100).max(4000),
@@ -110,7 +140,7 @@ const knowledgeChunkingConfigSchema = z
     minSize: z.number(),
     overlap: z.number(),
     strategy: z.enum(['auto', 'text', 'regex', 'recursive', 'sentence', 'token']).optional(),
-    strategyOptions: chunkingStrategyOptionsSchema.optional(),
+    strategyOptions: storedChunkingStrategyOptionsSchema.optional(),
   })
   .passthrough()
 

diff --git a/apps/sim/lib/chunkers/constants.ts b/apps/sim/lib/chunkers/constants.ts
@@ -0,0 +1,17 @@
+/**
+ * Bounds on the separator list a recursive chunking config may carry.
+ *
+ * `RecursiveChunker` scans the whole document once per separator and walks the
+ * list from the top for every oversized fragment, so the separator count is a
+ * direct multiplier on synchronous CPU per document. The work happens inside a
+ * split loop, which neither the processing `Promise.race` timeout nor the
+ * after-the-fact chunk-count cap can interrupt — the list has to be bounded on
+ * the way in instead.
+ *
+ * The largest built-in recipe (`markdown`) uses 16 separators, so 32 leaves room
+ * for a hand-tuned list without letting one config stall the processing tier.
+ */
+export const MAX_CHUNKING_SEPARATORS = 32
+
+/** Max characters in a single chunking separator. Real delimiters are a few characters. */
+export const MAX_CHUNKING_SEPARATOR_LENGTH = 100
diff --git a/apps/sim/lib/chunkers/recursive-chunker.test.ts b/apps/sim/lib/chunkers/recursive-chunker.test.ts
@@ -3,7 +3,8 @@
  */
 
 import { describe, expect, it } from 'vitest'
-import { RecursiveChunker } from './recursive-chunker'
+import { MAX_CHUNKING_SEPARATOR_LENGTH, MAX_CHUNKING_SEPARATORS } from '@/lib/chunkers/constants'
+import { RecursiveChunker } from '@/lib/chunkers/recursive-chunker'
 
 describe('RecursiveChunker', () => {
   describe('empty and whitespace input', () => {
@@ -101,6 +102,63 @@ describe('RecursiveChunker', () => {
     })
   })
 
+  describe('separator bounds', () => {
+    it.concurrent('ignores separators past the list bound', async () => {
+      const separators = [
+        ...Array.from({ length: MAX_CHUNKING_SEPARATORS }, (_, i) => `@@nomatch${i}@@`),
+        '---',
+      ]
+      const chunker = new RecursiveChunker({ chunkSize: 15, separators })
+      const text =
+        'Section one content here with words.---Section two content here with words.---Section three content here.'
+
+      const chunks = await chunker.chunk(text)
+
+      expect(chunks.length).toBeGreaterThan(1)
+      expect(chunks.some((chunk) => chunk.text.includes('---'))).toBe(true)
+    })
+
+    it.concurrent('splits on a separator that survives the clamp', async () => {
+      const separators = [
+        '---',
+        ...Array.from({ length: MAX_CHUNKING_SEPARATORS }, (_, i) => `@@nomatch${i}@@`),
+      ]
+      const chunker = new RecursiveChunker({ chunkSize: 15, separators })
+      const text =
+        'Section one content here with words.---Section two content here with words.---Section three content here.'
+
+      const chunks = await chunker.chunk(text)
+
+      expect(chunks.length).toBeGreaterThan(1)
+      expect(chunks.every((chunk) => !chunk.text.includes('---'))).toBe(true)
+    })
+
+    it.concurrent('drops a separator longer than the per-item bound', async () => {
+      const oversized = '|'.repeat(MAX_CHUNKING_SEPARATOR_LENGTH + 1)
+      const chunker = new RecursiveChunker({ chunkSize: 15, separators: [oversized, '---'] })
+      const text = `Section one content here.${oversized}Section two content.---Section three content.`
+
+      const chunks = await chunker.chunk(text)
+
+      expect(chunks.some((chunk) => chunk.text.includes('|'))).toBe(true)
+      expect(chunks.every((chunk) => !chunk.text.includes('---'))).toBe(true)
+    })
+
+    it.concurrent('falls back to the recipe when every separator is over the bound', async () => {
+      const oversized = '|'.repeat(MAX_CHUNKING_SEPARATOR_LENGTH + 1)
+      const text =
+        'Section one content here with words.\n\nSection two content here with words.\n\nSection three content.'
+
+      const chunks = await new RecursiveChunker({ chunkSize: 15, separators: [oversized] }).chunk(
+        text
+      )
+      const defaultChunks = await new RecursiveChunker({ chunkSize: 15 }).chunk(text)
+
+      expect(chunks.length).toBeGreaterThan(1)
+      expect(chunks).toEqual(defaultChunks)
+    })
+  })
+
   describe('recipe: plain', () => {
     it.concurrent('should use plain recipe by default', async () => {
       const chunker = new RecursiveChunker({ chunkSize: 20 })