diff --git a/apps/sim/lib/copilot/tools/handlers/materialize-file.test.ts b/apps/sim/lib/copilot/tools/handlers/materialize-file.test.ts
index bdad3967c45..d3e2751c277 100644
--- a/apps/sim/lib/copilot/tools/handlers/materialize-file.test.ts
+++ b/apps/sim/lib/copilot/tools/handlers/materialize-file.test.ts
@@ -5,22 +5,26 @@ import { dbChainMock, dbChainMockFns, resetDbChainMock } from '@sim/testing'
 import { beforeEach, describe, expect, it, vi } from 'vitest'
 
 const {
+  mockAllocateUniqueWorkspaceFileName,
   mockCheckStorageQuotaForBillingContext,
   mockDecompress,
   mockFetchBuffer,
   mockFindFolder,
   mockFindUpload,
+  mockGetWorkspaceFile,
   mockHasCloudStorage,
   mockHeadObject,
   mockIncrementStorageUsageForBillingContextInTx,
   mockMaybeNotifyStorageLimitForBillingContext,
   mockResolveStorageBillingContext,
 } = vi.hoisted(() => ({
+  mockAllocateUniqueWorkspaceFileName: vi.fn(),
   mockCheckStorageQuotaForBillingContext: vi.fn(),
   mockDecompress: vi.fn(),
   mockFetchBuffer: vi.fn(),
   mockFindFolder: vi.fn(),
   mockFindUpload: vi.fn(),
+  mockGetWorkspaceFile: vi.fn(),
   mockHasCloudStorage: vi.fn(),
   mockHeadObject: vi.fn(),
   mockIncrementStorageUsageForBillingContextInTx: vi.fn(),
@@ -41,7 +45,9 @@ vi.mock('@/lib/uploads', () => ({
 }))
 
 vi.mock('@/lib/uploads/contexts/workspace/workspace-file-manager', () => ({
+  allocateUniqueWorkspaceFileName: mockAllocateUniqueWorkspaceFileName,
   fetchWorkspaceFileBuffer: mockFetchBuffer,
+  getWorkspaceFile: mockGetWorkspaceFile,
 }))
 
 vi.mock('@/lib/uploads/contexts/workspace/workspace-file-folder-manager', () => ({
@@ -76,7 +82,9 @@ vi.mock('@/lib/billing/storage', () => ({
 }))
 
 vi.mock('@/lib/copilot/vfs/path-utils', () => ({
-  canonicalWorkspaceFilePath: vi.fn(() => 'files/report.txt'),
+  canonicalWorkspaceFilePath: vi.fn(
+    ({ name }: { name: string }) => `files/${encodeURIComponent(name)}`
+  ),
   encodeVfsPathSegments: (segments: string[]) =>
     segments.map((s) => encodeURIComponent(s)).join('/'),
 }))
@@ -237,6 +245,8 @@ describe('executeMaterializeFile - save storage transition', () => {
     vi.clearAllMocks()
     resetDbChainMock()
     mockFindUpload.mockResolvedValue(mothershipRow)
+    mockAllocateUniqueWorkspaceFileName.mockResolvedValue('report.txt')
+    mockGetWorkspaceFile.mockResolvedValue({ id: 'file-1', name: 'report.txt' })
     mockHeadObject.mockResolvedValue({ size: 250, contentType: 'text/plain' })
     mockHasCloudStorage.mockReturnValue(true)
     mockResolveStorageBillingContext.mockResolvedValue(STORAGE_CONTEXT)
@@ -278,6 +288,11 @@ describe('executeMaterializeFile - save storage transition', () => {
     expect(result.success).toBe(true)
     expect(mockHeadObject).toHaveBeenCalledWith('mothership/file-1', 'mothership')
     expect(mockCheckStorageQuotaForBillingContext).toHaveBeenCalledWith(STORAGE_CONTEXT, 250)
+    expect(mockAllocateUniqueWorkspaceFileName).toHaveBeenCalledWith(
+      context.workspaceId,
+      'report.txt',
+      null
+    )
     expect(dbChainMockFns.set).toHaveBeenCalledWith(
       expect.objectContaining({ context: 'workspace', chatId: null, size: 250 })
     )
@@ -287,8 +302,129 @@ describe('executeMaterializeFile - save storage transition', () => {
     )
   })
 
+  it('materializes with an available root-level copy name', async () => {
+    mockFindUpload.mockResolvedValueOnce({
+      ...mothershipRow,
+      originalName: 'image.png',
+      displayName: 'image.png',
+    })
+    mockAllocateUniqueWorkspaceFileName.mockResolvedValueOnce('image (1).png')
+    dbChainMockFns.returning.mockResolvedValueOnce([
+      { id: 'file-1', originalName: 'image (1).png' },
+    ])
+
+    const result = await executeMaterializeFile(
+      { fileNames: ['image.png'], operation: 'save' },
+      context
+    )
+
+    expect(result.success).toBe(true)
+    expect(mockAllocateUniqueWorkspaceFileName).toHaveBeenCalledWith(
+      context.workspaceId,
+      'image.png',
+      null
+    )
+    expect(dbChainMockFns.set).toHaveBeenCalledWith(
+      expect.objectContaining({
+        context: 'workspace',
+        originalName: 'image (1).png',
+        displayName: 'image (1).png',
+      })
+    )
+    expect(result.output).toEqual({ succeeded: ['image (1).png'], failed: [] })
+    expect(result.resources).toEqual([{ type: 'file', id: 'file-1', title: 'image (1).png' }])
+  })
+
+  it('reallocates and retries when a concurrent root-level write claims the name', async () => {
+    const nameCollision = Object.assign(new Error('duplicate workspace file name'), {
+      code: '23505',
+      constraint_name: 'workspace_files_workspace_folder_name_active_unique',
+    })
+    mockFindUpload.mockResolvedValueOnce({
+      ...mothershipRow,
+      originalName: 'image.png',
+      displayName: 'image.png',
+    })
+    mockAllocateUniqueWorkspaceFileName
+      .mockResolvedValueOnce('image (1).png')
+      .mockResolvedValueOnce('image (2).png')
+    dbChainMockFns.returning
+      .mockRejectedValueOnce(nameCollision)
+      .mockResolvedValueOnce([{ id: 'file-1', originalName: 'image (2).png' }])
+
+    const result = await executeMaterializeFile(
+      { fileNames: ['image.png'], operation: 'save' },
+      context
+    )
+
+    expect(result.success).toBe(true)
+    expect(mockAllocateUniqueWorkspaceFileName).toHaveBeenCalledTimes(2)
+    expect(mockAllocateUniqueWorkspaceFileName).toHaveBeenNthCalledWith(
+      1,
+      context.workspaceId,
+      'image.png',
+      null
+    )
+    expect(mockAllocateUniqueWorkspaceFileName).toHaveBeenNthCalledWith(
+      2,
+      context.workspaceId,
+      'image.png',
+      null
+    )
+    expect(dbChainMockFns.transaction).toHaveBeenCalledTimes(2)
+    expect(dbChainMockFns.set).toHaveBeenNthCalledWith(
+      1,
+      expect.objectContaining({ originalName: 'image (1).png' })
+    )
+    expect(dbChainMockFns.set).toHaveBeenNthCalledWith(
+      2,
+      expect.objectContaining({ originalName: 'image (2).png' })
+    )
+    expect(mockIncrementStorageUsageForBillingContextInTx).toHaveBeenCalledTimes(1)
+    expect(result.output).toEqual({ succeeded: ['image (2).png'], failed: [] })
+    expect(result.resources).toEqual([{ type: 'file', id: 'file-1', title: 'image (2).png' }])
+  })
+
+  it('stops after the bounded number of root-level name collisions', async () => {
+    const nameCollision = Object.assign(new Error('duplicate workspace file name'), {
+      code: '23505',
+      constraint_name: 'workspace_files_workspace_folder_name_active_unique',
+    })
+    dbChainMockFns.returning.mockRejectedValue(nameCollision)
+
+    const result = await executeMaterializeFile(
+      { fileNames: ['report.txt'], operation: 'save' },
+      context
+    )
+
+    expect(result.success).toBe(false)
+    expect(mockAllocateUniqueWorkspaceFileName).toHaveBeenCalledTimes(8)
+    expect(dbChainMockFns.transaction).toHaveBeenCalledTimes(8)
+    expect(mockIncrementStorageUsageForBillingContextInTx).not.toHaveBeenCalled()
+    expect(mockMaybeNotifyStorageLimitForBillingContext).not.toHaveBeenCalled()
+  })
+
+  it('does not retry unique violations from a different constraint', async () => {
+    const keyCollision = Object.assign(new Error('duplicate workspace file key'), {
+      code: '23505',
+      constraint_name: 'workspace_files_key_active_unique',
+    })
+    dbChainMockFns.returning.mockRejectedValueOnce(keyCollision)
+
+    const result = await executeMaterializeFile(
+      { fileNames: ['report.txt'], operation: 'save' },
+      context
+    )
+
+    expect(result.success).toBe(false)
+    expect(mockAllocateUniqueWorkspaceFileName).toHaveBeenCalledTimes(1)
+    expect(dbChainMockFns.transaction).toHaveBeenCalledTimes(1)
+    expect(mockIncrementStorageUsageForBillingContextInTx).not.toHaveBeenCalled()
+  })
+
   it('treats a lost conditional transition as a replay no-op', async () => {
     dbChainMockFns.returning.mockResolvedValueOnce([])
+    mockGetWorkspaceFile.mockResolvedValueOnce({ id: 'file-1', name: 'report (1).txt' })
 
     const result = await executeMaterializeFile(
       { fileNames: ['report.txt'], operation: 'save' },
@@ -296,6 +432,37 @@ describe('executeMaterializeFile - save storage transition', () => {
     )
 
     expect(result.success).toBe(true)
+    expect(mockGetWorkspaceFile).toHaveBeenCalledWith(context.workspaceId, 'file-1', {
+      throwOnError: true,
+    })
+    expect(result.output).toEqual({ succeeded: ['report (1).txt'], failed: [] })
+    expect(result.resources).toEqual([{ type: 'file', id: 'file-1', title: 'report (1).txt' }])
+    expect(mockIncrementStorageUsageForBillingContextInTx).not.toHaveBeenCalled()
+    expect(mockMaybeNotifyStorageLimitForBillingContext).not.toHaveBeenCalled()
+  })
+
+  it('fails a replay when the materialized workspace file no longer exists', async () => {
+    dbChainMockFns.returning.mockResolvedValueOnce([])
+    mockGetWorkspaceFile.mockResolvedValueOnce(null)
+
+    const result = await executeMaterializeFile(
+      { fileNames: ['report.txt'], operation: 'save' },
+      context
+    )
+
+    expect(result.success).toBe(false)
+    expect(result.output).toEqual({
+      succeeded: [],
+      failed: [
+        {
+          fileName: 'report.txt',
+          error: 'Upload no longer available: "report.txt".',
+        },
+      ],
+    })
+    expect(mockGetWorkspaceFile).toHaveBeenCalledWith(context.workspaceId, 'file-1', {
+      throwOnError: true,
+    })
     expect(mockIncrementStorageUsageForBillingContextInTx).not.toHaveBeenCalled()
     expect(mockMaybeNotifyStorageLimitForBillingContext).not.toHaveBeenCalled()
   })
diff --git a/apps/sim/lib/copilot/tools/handlers/materialize-file.ts b/apps/sim/lib/copilot/tools/handlers/materialize-file.ts
index 3e2abda31a2..69314264ec9 100644
--- a/apps/sim/lib/copilot/tools/handlers/materialize-file.ts
+++ b/apps/sim/lib/copilot/tools/handlers/materialize-file.ts
@@ -2,7 +2,12 @@ import { AuditAction, AuditResourceType, recordAudit } from '@sim/audit'
 import { db } from '@sim/db'
 import { folder as folderTable, workflow, workspaceFiles } from '@sim/db/schema'
 import { createLogger } from '@sim/logger'
-import { getErrorMessage, toError } from '@sim/utils/errors'
+import {
+  getErrorMessage,
+  getPostgresConstraintName,
+  getPostgresErrorCode,
+  toError,
+} from '@sim/utils/errors'
 import { generateId } from '@sim/utils/id'
 import { and, eq, isNull, sql } from 'drizzle-orm'
 import {
@@ -23,7 +28,11 @@ import {
   MAX_ARCHIVE_BYTES,
 } from '@/lib/uploads/archive'
 import { findWorkspaceFileFolderIdByPath } from '@/lib/uploads/contexts/workspace/workspace-file-folder-manager'
-import { fetchWorkspaceFileBuffer } from '@/lib/uploads/contexts/workspace/workspace-file-manager'
+import {
+  allocateUniqueWorkspaceFileName,
+  fetchWorkspaceFileBuffer,
+  getWorkspaceFile,
+} from '@/lib/uploads/contexts/workspace/workspace-file-manager'
 import { hasCloudStorage, headObject } from '@/lib/uploads/core/storage-service'
 import { isArchiveFileName } from '@/lib/uploads/utils/file-utils'
 import { parseWorkflowJson } from '@/lib/workflows/operations/import-export'
@@ -32,6 +41,8 @@ import { deduplicateWorkflowName } from '@/lib/workflows/utils'
 import { extractWorkflowMetadata } from '@/app/api/v1/admin/types'
 
 const logger = createLogger('MaterializeFile')
+const MAX_MATERIALIZE_NAME_RETRIES = 8
+const WORKSPACE_FILE_NAME_UNIQUE_INDEX = 'workspace_files_workspace_folder_name_active_unique'
 
 function toFileRecord(row: typeof workspaceFiles.$inferSelect) {
   const pathPrefix = getServePathPrefix()
@@ -107,46 +118,76 @@ async function executeSave(
    * workspace lock before locking its payer. Any quota/stale-payer failure
    * rolls back the row transition.
    */
-  const transition = await db.transaction(async (tx) => {
-    await tx.execute(sql`SELECT 1 FROM workspace WHERE id = ${workspaceId} FOR UPDATE`)
-
-    const [updated] = await tx
-      .update(workspaceFiles)
-      .set({
-        context: 'workspace',
-        // A workspace file has no birth chat or message — clear both provenance
-        // fields so the row reads as workspace-owned, not stale chat-owned.
-        chatId: null,
-        messageId: null,
-        originalName: row.displayName ?? row.originalName,
-        size: verifiedSize,
-      })
-      .where(
-        and(
-          eq(workspaceFiles.id, row.id),
-          eq(workspaceFiles.workspaceId, workspaceId),
-          eq(workspaceFiles.chatId, chatId),
-          eq(workspaceFiles.context, 'mothership'),
-          isNull(workspaceFiles.deletedAt)
-        )
-      )
-      .returning({ id: workspaceFiles.id, originalName: workspaceFiles.originalName })
+  let transition: {
+    updated: { id: string; originalName: string }
+    updatedUsage: number | undefined
+  } | null = null
 
-    if (!updated) {
-      return null
-    }
+  for (let attempt = 0; attempt < MAX_MATERIALIZE_NAME_RETRIES; attempt++) {
+    const materializedName = await allocateUniqueWorkspaceFileName(workspaceId, displayName, null)
 
-    const updatedUsage = await incrementStorageUsageForBillingContextInTx(
-      tx,
-      billingContext,
-      verifiedSize
-    )
-    return { updated, updatedUsage }
-  })
+    try {
+      transition = await db.transaction(async (tx) => {
+        await tx.execute(sql`SELECT 1 FROM workspace WHERE id = ${workspaceId} FOR UPDATE`)
+
+        const [updated] = await tx
+          .update(workspaceFiles)
+          .set({
+            context: 'workspace',
+            // A workspace file has no birth chat or message — clear both provenance
+            // fields so the row reads as workspace-owned, not stale chat-owned.
+            chatId: null,
+            messageId: null,
+            originalName: materializedName,
+            displayName: materializedName,
+            size: verifiedSize,
+          })
+          .where(
+            and(
+              eq(workspaceFiles.id, row.id),
+              eq(workspaceFiles.workspaceId, workspaceId),
+              eq(workspaceFiles.chatId, chatId),
+              eq(workspaceFiles.context, 'mothership'),
+              isNull(workspaceFiles.deletedAt)
+            )
+          )
+          .returning({ id: workspaceFiles.id, originalName: workspaceFiles.originalName })
 
-  const updated = transition?.updated ?? {
-    id: row.id,
-    originalName: row.displayName ?? row.originalName,
+        if (!updated) {
+          return null
+        }
+
+        const updatedUsage = await incrementStorageUsageForBillingContextInTx(
+          tx,
+          billingContext,
+          verifiedSize
+        )
+        return { updated, updatedUsage }
+      })
+      break
+    } catch (error) {
+      const isNameCollision =
+        getPostgresErrorCode(error) === '23505' &&
+        getPostgresConstraintName(error) === WORKSPACE_FILE_NAME_UNIQUE_INDEX
+      if (!isNameCollision || attempt === MAX_MATERIALIZE_NAME_RETRIES - 1) {
+        throw error
+      }
+      logger.warn('Workspace file name was claimed during materialization; retrying', {
+        fileName,
+        materializedName,
+        attempt: attempt + 1,
+      })
+    }
+  }
+
+  const replayedFile = transition
+    ? null
+    : await getWorkspaceFile(workspaceId, row.id, { throwOnError: true })
+  const updated =
+    transition?.updated ??
+    (replayedFile ? { id: replayedFile.id, originalName: replayedFile.name } : null)
+  if (!updated) {
+    return { success: false, error: `Upload no longer available: "${fileName}".` }
   }
   if (transition?.updatedUsage !== undefined) {
     void maybeNotifyStorageLimitForBillingContext(billingContext, transition.updatedUsage)
@@ -530,7 +571,11 @@ export async function executeMaterializeFile(
       }
 
       if (result.success) {
-        succeeded.push(fileName)
+        const materializedName =
+          operation === 'save'
+            ? result.resources?.find((resource) => resource.type === 'file')?.title
+            : undefined
+        succeeded.push(materializedName ?? fileName)
         if (result.resources) resources.push(...result.resources)
       } else {
         failed.push({ fileName, error: result.error ?? 'Failed to materialize file' })
@@ -541,6 +586,8 @@ export async function executeMaterializeFile(
         operation,
         chatId: context.chatId,
         error: toError(err).message,
+        postgresCode: getPostgresErrorCode(err),
+        postgresConstraint: getPostgresConstraintName(err),
       })
       failed.push({
         fileName,