test(auth): cover minted delegation through workspace and knowledge u…

…se cases Workspace admission requires the same chat id on the invocation and the grant, so the GitLab fixture and the new cases use the principals Copilot actually mints. Co-authored-by: Cursor <cursoragent@cursor.com>
mzxchandra · Oct 17, 2026 · Oct 17, 2026 · Oct 17, 2026 · Oct 17, 2026 · Oct 17, 2026
commit 0374a900dd22c0b0a1470ed89d4e4eb3a6a4e9f4
diff --git a/apps/sim/lib/knowledge/__integration__/gitlab-workspace.integration.ts b/apps/sim/lib/knowledge/__integration__/gitlab-workspace.integration.ts
@@ -17,6 +17,7 @@ import {
 } from '@sim/db/schema'
 import { deleteWorkspaceFixture } from '@sim/db/testing/workspace-fixtures'
 import { generateId } from '@sim/utils/id'
+import { compareStrings } from '@sim/utils/string'
 import { and, eq, inArray, isNull } from 'drizzle-orm'
 import { afterAll, beforeAll, expect, it, vi } from 'vitest'
 
@@ -42,7 +43,10 @@ vi.mock('@/lib/embeddings', async () => ({
   }),
 }))
 
+import { hasResourceOperationGrant } from '@sim/auth/principal'
+import { copilotRequestPrincipal } from '@/lib/api/server/routes/copilot-request'
 import { decryptApiKey } from '@/lib/api-key/crypto'
+import { withWorkspaceInvocationScope } from '@/lib/core/application/workspace-invocation-scope'
 import { encryptSecret } from '@/lib/core/security/encryption'
 import {
   createKnowledgeAclFixtureIds,
@@ -54,6 +58,10 @@ import {
 } from '@/lib/knowledge/application/connectors'
 import { readKnowledgeDocument } from '@/lib/knowledge/application/documents'
 import { searchKnowledge } from '@/lib/knowledge/application/search'
+import { executeCopilotKnowledgeUseCase } from '@/lib/mothership/application/execute-knowledge-use-case'
+import { markCopilotProjectFileRequest } from '@/lib/mothership/application/execute-project-file-use-case'
+import { createCopilotResourceAdmission } from '@/lib/mothership/auth/application-delegation'
+import { getProjectFileMetadata, projectFileOperations } from '@/lib/projects/files/application'
 
 const ids = createKnowledgeAclFixtureIds()
 const sourceConfig = {
@@ -71,6 +79,34 @@ const input = {
   syncIntervalMinutes: 1440,
 }
 
+function admittedProjectFileGrant(userId: string) {
+  const chatId = generateId()
+  const request = new Request('http://localhost:3000/api/v2/projects/project/files/file/metadata')
+  markCopilotProjectFileRequest(
+    request,
+    {
+      userId,
+      chatId,
+      toolCallId: generateId(),
+      copilotToolExecution: true,
+      copilotResourceAdmission: createCopilotResourceAdmission({
+        userId,
+        invocation: { kind: 'chat', chatId },
+      }),
+    },
+    { projectId: generateId(), fileId: generateId() }
+  )
+  const principal = copilotRequestPrincipal(
+    request,
+    projectFileOperations.readMetadata,
+    getProjectFileMetadata
+  )
+  if (!principal || !hasResourceOperationGrant(principal)) {
+    throw new Error('Project file request did not mint a resource grant')
+  }
+  return principal
+}
+
 beforeAll(async () => {
   fixture.root = mkdtempSync(path.join(tmpdir(), 'sim-gitlab-workspace-'))
   await seedKnowledgeAclFixture(ids)
@@ -128,6 +164,7 @@ it.each([
 ])(
   'creates, syncs, edits, and searches a workspace GitLab source through $surface using $apiKey',
   async ({ surface, apiKey }) => {
+    const chatId = generateId()
     const caller =
       surface === 'application'
         ? principal
@@ -139,12 +176,12 @@ it.each([
             audience: 'sim:knowledge',
             issuedAt: new Date(),
             expiresAt: new Date(Date.now() + 60000),
-            invocation: { kind: 'chat', chatId: generateId() } as const,
+            invocation: { kind: 'chat' as const, chatId },
             grant: {
-              kind: 'entity',
-              owner: { entityType: 'workspace', entityId: ids.workspaceId },
-              restrictions: { chatId: generateId() },
-            } as const,
+              kind: 'entity' as const,
+              owner: { entityType: 'workspace' as const, entityId: ids.workspaceId },
+              restrictions: { chatId },
+            },
           }
     const { connector } = await createKnowledgeConnector.execute({
       principal: caller,
@@ -265,3 +302,74 @@ it('still refuses workspace access on a Search index before contacting GitLab',
   ).rejects.toThrow('Search sources must support per-person access or source permissions')
   expect(fixture.fetch.mock.calls).toHaveLength(requestCount)
 })
+
+it('creates a GitLab connector for a writer through the minted Copilot knowledge principal', async () => {
+  const chatId = generateId()
+  const { connector } = await withWorkspaceInvocationScope(
+    { workspaceId: ids.workspaceId, organizationId: ids.organizationId },
+    () =>
+      executeCopilotKnowledgeUseCase(
+        {
+          userId: ids.aliceId,
+          workspaceId: ids.workspaceId,
+          chatId,
+          toolCallId: generateId(),
+          copilotToolExecution: true,
+        },
+        createKnowledgeConnector,
+        input
+      )
+  )
+
+  expect(JSON.stringify(connector)).not.toContain(input.apiKey)
+  const [stored] = await db
+    .select()
+    .from(knowledgeConnector)
+    .where(eq(knowledgeConnector.id, connector.id))
+  if (!stored) throw new Error('Connector was not stored')
+  const encryptedApiKey = stored.encryptedApiKey
+  if (!encryptedApiKey) throw new Error('Connector was stored without an API key')
+  expect(stored.accessMode).toBe('workspace')
+  expect(encryptedApiKey).not.toBe(input.apiKey)
+  expect((await decryptApiKey(encryptedApiKey)).decrypted).toBe(input.apiKey)
+  await expect
+    .poll(
+      async () => {
+        const [row] = await db
+          .select({ status: knowledgeConnector.status, error: knowledgeConnector.lastSyncError })
+          .from(knowledgeConnector)
+          .where(eq(knowledgeConnector.id, connector.id))
+        return row
+      },
+      { timeout: 15000 }
+    )
+    .toEqual({ status: 'active', error: null })
+}, 30000)
+
+it('refuses knowledge connector create for a project file grant', async () => {
+  const connectorIds = async () => {
+    const rows = await db
+      .select({ id: knowledgeConnector.id })
+      .from(knowledgeConnector)
+      .where(eq(knowledgeConnector.knowledgeBaseId, ids.knowledgeBaseId))
+    return rows.map((row) => row.id).sort(compareStrings)
+  }
+  const before = await connectorIds()
+  const requestCount = fixture.fetch.mock.calls.length
+
+  await expect(
+    withWorkspaceInvocationScope(
+      { workspaceId: ids.workspaceId, organizationId: ids.organizationId },
+      () =>
+        createKnowledgeConnector.execute({
+          principal: admittedProjectFileGrant(ids.aliceId),
+          input,
+        })
+    )
+  ).rejects.toMatchObject({
+    detailCode: 'PRINCIPAL_KIND_NOT_PERMITTED',
+    message: 'Principal kind delegated cannot perform operation knowledge.connectors.create',
+  })
+  expect(fixture.fetch.mock.calls).toHaveLength(requestCount)
+  expect(await connectorIds()).toEqual(before)
+})
diff --git a/apps/sim/lib/workspace-files/__integration__/copilot-file-versions.integration.ts b/apps/sim/lib/workspace-files/__integration__/copilot-file-versions.integration.ts
@@ -3,6 +3,7 @@ import { mkdtempSync } from 'node:fs'
 import { rm } from 'node:fs/promises'
 import { tmpdir } from 'node:os'
 import path from 'node:path'
+import { hasResourceOperationGrant, parsePrincipal, serializePrincipal } from '@sim/auth/principal'
 import { db } from '@sim/db'
 import {
   auditLog,
@@ -30,6 +31,7 @@ vi.mock('@/lib/uploads/core/setup.server', () => ({
   },
 }))
 
+import { copilotRequestPrincipal } from '@/lib/api/server/routes/copilot-request'
 import { ContentDeliveryUnobservedError } from '@/lib/core/application'
 import { withWorkspaceInvocationScope } from '@/lib/core/application/workspace-invocation-scope'
 import { encryptSecret } from '@/lib/core/security/encryption'
@@ -41,7 +43,14 @@ import { runCli } from '@/lib/mothership/agent-cli/run-cli'
 import { createScopedCliTransport } from '@/lib/mothership/agent-cli/scoped-transport'
 import { createAgentCliTransport } from '@/lib/mothership/agent-cli/transport'
 import { createWorkbenchFileProvenance } from '@/lib/mothership/agent-cli/workbench-file-provenance'
-import { createCopilotChatPrincipal } from '@/lib/mothership/auth/application-delegation'
+import { markCopilotProjectFileRequest } from '@/lib/mothership/application/execute-project-file-use-case'
+import {
+  COPILOT_APPLICATION_DELEGATION_TTL_MS,
+  createCopilotChatPrincipal,
+  createCopilotResourceAdmission,
+  createTrustedCopilotPrincipal,
+} from '@/lib/mothership/auth/application-delegation'
+import { getProjectFileMetadata, projectFileOperations } from '@/lib/projects/files/application'
 import {
   updateWorkspaceFileContent,
   uploadWorkspaceFile,
@@ -52,6 +61,7 @@ import {
 } from '@/lib/uploads/contexts/workspace/file-secret-provenance'
 import { WORKSPACE_FILES_DELEGATION_AUDIENCE } from '@/lib/workspace-files/application/authorization'
 import { downloadWorkspaceFileStream } from '@/lib/workspace-files/application/download-workspace-file'
+import { revertWorkspaceFileVersion } from '@/lib/workspace-files/application/file-versions'
 import { projectResolvedSecretModelContent } from '@/executor/utils/resolved-secret-content-projection'
 import { ResolvedSecretTraceRegistry } from '@/executor/utils/resolved-secret-trace-registry'
 import '@/app/api/v2/files/[fileId]/text/route'
@@ -182,6 +192,34 @@ describe('chat-delegated file version history', () => {
     return new ResolvedSecretTraceRegistry([], { userId, workspaceId: fixture.workspaceId })
   }
 
+  function admittedProjectFileGrant(userId: string) {
+    const chatId = generateId()
+    const request = new Request('http://localhost:3000/api/v2/projects/project/files/file/metadata')
+    markCopilotProjectFileRequest(
+      request,
+      {
+        userId,
+        chatId,
+        toolCallId: generateId(),
+        copilotToolExecution: true,
+        copilotResourceAdmission: createCopilotResourceAdmission({
+          userId,
+          invocation: { kind: 'chat', chatId },
+        }),
+      },
+      { projectId: generateId(), fileId: generateId() }
+    )
+    const principal = copilotRequestPrincipal(
+      request,
+      projectFileOperations.readMetadata,
+      getProjectFileMetadata
+    )
+    if (!principal || !hasResourceOperationGrant(principal)) {
+      throw new Error('Project file request did not mint a resource grant')
+    }
+    return principal
+  }
+
   function versionRows(fileId: string) {
     return db
       .select({ version: workspaceFileVersion.version, source: workspaceFileVersion.source })
@@ -285,6 +323,88 @@ describe('chat-delegated file version history', () => {
     expect((await versionRows(fixture.fileId)).map((row) => row.version)).toEqual([1, 2, 3])
   })
 
+  it('admits a file revert after the minted Copilot principal is serialized and restored', async () => {
+    const fixture = await seedVersionedFile()
+    const chatId = generateId()
+    const restored = parsePrincipal(
+      serializePrincipal(
+        createTrustedCopilotPrincipal(
+          {
+            userId: fixture.aliceId,
+            workspaceId: fixture.workspaceId,
+            chatId,
+            delegationId: `copilot-chat:${chatId}`,
+          },
+          {
+            audience: WORKSPACE_FILES_DELEGATION_AUDIENCE,
+            ttlMs: COPILOT_APPLICATION_DELEGATION_TTL_MS,
+          }
+        )
+      )
+    )
+
+    const result = await withWorkspaceInvocationScope(
+      { workspaceId: fixture.workspaceId, organizationId: fixture.organizationId },
+      () =>
+        revertWorkspaceFileVersion.execute({
+          principal: restored,
+          input: {
+            fileId: fixture.fileId,
+            assertedWorkspaceId: fixture.workspaceId,
+            version: 1,
+            expectedCurrentVersion: 3,
+          },
+        })
+    )
+
+    expect(result).toMatchObject({
+      reverted: true,
+      version: { version: 4, source: 'revert', restoredFromVersion: 1 },
+    })
+    expect((await versionRows(fixture.fileId)).map((row) => row.version)).toEqual([1, 2, 3, 4])
+    await vi.waitFor(async () => {
+      const [audit] = await db
+        .select({ actorId: auditLog.actorId, metadata: auditLog.metadata })
+        .from(auditLog)
+        .where(
+          and(
+            eq(auditLog.workspaceId, fixture.workspaceId),
+            eq(auditLog.resourceId, fixture.fileId)
+          )
+        )
+      expect(audit).toMatchObject({
+        actorId: fixture.aliceId,
+        metadata: {
+          operation: 'files.versions.revert',
+          actor: { kind: 'delegated', serviceId: 'copilot' },
+        },
+      })
+    })
+  })
+
+  it('refuses a workspace file revert for a project file grant', async () => {
+    const fixture = await seedVersionedFile()
+
+    await expect(
+      withWorkspaceInvocationScope(
+        { workspaceId: fixture.workspaceId, organizationId: fixture.organizationId },
+        () =>
+          revertWorkspaceFileVersion.execute({
+            principal: admittedProjectFileGrant(fixture.aliceId),
+            input: {
+              fileId: fixture.fileId,
+              assertedWorkspaceId: fixture.workspaceId,
+              version: 1,
+            },
+          })
+      )
+    ).rejects.toMatchObject({
+      detailCode: 'PRINCIPAL_KIND_NOT_PERMITTED',
+      message: 'Principal kind delegated cannot perform operation files.versions.revert',
+    })
+    expect((await versionRows(fixture.fileId)).map((row) => row.version)).toEqual([1, 2, 3])
+  })
+
   it('keeps version delete and download direct-only', async () => {
     const fixture = await seedVersionedFile()
     const chat = chatTransport(fixture, fixture.aliceId)