Create google drive e2e test (#3635)

* Create e2e google drive test

* Drive sync issue

* Add endpoints for group syncing

* google e2e fixes/improvements and add xfail to zendesk tests

* mypy errors

* Key change

* Small changes

* Merged main to fix group sync issue

* Update test_permission_sync.py

* Update google_drive_api_utils.py

* Update test_zendesk_connector.py

---------

Co-authored-by: hagen-danswer <hagen@danswer.ai>

backend/onyx/server/documents/cc_pair.py

@@ -15,6 +15,9 @@ from onyx.background.celery.celery_utils import get_deletion_attempt_snapshot
 from onyx.background.celery.tasks.doc_permission_syncing.tasks import (
     try_creating_permissions_sync_task,
 )
+from onyx.background.celery.tasks.external_group_syncing.tasks import (
+    try_creating_external_group_sync_task,
+)
 from onyx.background.celery.tasks.pruning.tasks import (
     try_creating_prune_generator_task,
 )
@@ -443,6 +446,78 @@ def sync_cc_pair(
     )
 
 
+@router.get("/admin/cc-pair/{cc_pair_id}/sync-groups")
+def get_cc_pair_latest_group_sync(
+    cc_pair_id: int,
+    user: User = Depends(current_curator_or_admin_user),
+    db_session: Session = Depends(get_session),
+) -> datetime | None:
+    cc_pair = get_connector_credential_pair_from_id_for_user(
+        cc_pair_id=cc_pair_id,
+        db_session=db_session,
+        user=user,
+        get_editable=False,
+    )
+    if not cc_pair:
+        raise HTTPException(
+            status_code=400,
+            detail="cc_pair not found for current user's permissions",
+        )
+
+    return cc_pair.last_time_external_group_sync
+
+
+@router.post("/admin/cc-pair/{cc_pair_id}/sync-groups")
+def sync_cc_pair_groups(
+    cc_pair_id: int,
+    user: User = Depends(current_curator_or_admin_user),
+    db_session: Session = Depends(get_session),
+    tenant_id: str | None = Depends(get_current_tenant_id),
+) -> StatusResponse[list[int]]:
+    """Triggers group sync on a particular cc_pair immediately"""
+
+    cc_pair = get_connector_credential_pair_from_id_for_user(
+        cc_pair_id=cc_pair_id,
+        db_session=db_session,
+        user=user,
+        get_editable=False,
+    )
+    if not cc_pair:
+        raise HTTPException(
+            status_code=400,
+            detail="Connection not found for current user's permissions",
+        )
+
+    r = get_redis_client(tenant_id=tenant_id)
+
+    redis_connector = RedisConnector(tenant_id, cc_pair_id)
+    if redis_connector.external_group_sync.fenced:
+        raise HTTPException(
+            status_code=HTTPStatus.CONFLICT,
+            detail="External group sync task already in progress.",
+        )
+
+    logger.info(
+        f"External group sync cc_pair={cc_pair_id} "
+        f"connector_id={cc_pair.connector_id} "
+        f"credential_id={cc_pair.credential_id} "
+        f"{cc_pair.connector.name} connector."
+    )
+    tasks_created = try_creating_external_group_sync_task(
+        primary_app, cc_pair_id, r, CURRENT_TENANT_ID_CONTEXTVAR.get()
+    )
+    if not tasks_created:
+        raise HTTPException(
+            status_code=HTTPStatus.INTERNAL_SERVER_ERROR,
+            detail="External group sync task creation failed.",
+        )
+
+    return StatusResponse(
+        success=True,
+        message="Successfully created the external group sync task.",
+    )
+
+
 @router.get("/admin/cc-pair/{cc_pair_id}/get-docs-sync-status")
 def get_docs_sync_status(
     cc_pair_id: int,

backend/tests/integration/common_utils/managers/cc_pair.py

@@ -432,30 +432,61 @@ class CCPairManager:
             if user_performing_action
             else GENERAL_HEADERS,
         )
-        #
         if result.status_code != 409:
             result.raise_for_status()
 
+        group_sync_result = requests.post(
+            url=f"{API_SERVER_URL}/manage/admin/cc-pair/{cc_pair.id}/sync-groups",
+            headers=user_performing_action.headers
+            if user_performing_action
+            else GENERAL_HEADERS,
+        )
+        if group_sync_result.status_code != 409:
+            group_sync_result.raise_for_status()
+
     @staticmethod
-    def get_sync_task(
+    def get_doc_sync_task(
         cc_pair: DATestCCPair,
         user_performing_action: DATestUser | None = None,
     ) -> datetime | None:
-        response = requests.get(
+        doc_sync_response = requests.get(
             url=f"{API_SERVER_URL}/manage/admin/cc-pair/{cc_pair.id}/sync-permissions",
             headers=user_performing_action.headers
             if user_performing_action
             else GENERAL_HEADERS,
         )
-        response.raise_for_status()
-        response_str = response.json()
+        doc_sync_response.raise_for_status()
+        doc_sync_response_str = doc_sync_response.json()
 
         # If the response itself is a datetime string, parse it
-        if not isinstance(response_str, str):
+        if not isinstance(doc_sync_response_str, str):
             return None
 
         try:
-            return datetime.fromisoformat(response_str)
+            return datetime.fromisoformat(doc_sync_response_str)
+        except ValueError:
+            return None
+
+    @staticmethod
+    def get_group_sync_task(
+        cc_pair: DATestCCPair,
+        user_performing_action: DATestUser | None = None,
+    ) -> datetime | None:
+        group_sync_response = requests.get(
+            url=f"{API_SERVER_URL}/manage/admin/cc-pair/{cc_pair.id}/sync-groups",
+            headers=user_performing_action.headers
+            if user_performing_action
+            else GENERAL_HEADERS,
+        )
+        group_sync_response.raise_for_status()
+        group_sync_response_str = group_sync_response.json()
+
+        # If the response itself is a datetime string, parse it
+        if not isinstance(group_sync_response_str, str):
+            return None
+
+        try:
+            return datetime.fromisoformat(group_sync_response_str)
         except ValueError:
             return None
 
@@ -498,15 +529,37 @@ class CCPairManager:
         timeout: float = MAX_DELAY,
         number_of_updated_docs: int = 0,
         user_performing_action: DATestUser | None = None,
+        # Sometimes waiting for a group sync is not necessary
+        should_wait_for_group_sync: bool = True,
+        # Sometimes waiting for a vespa sync is not necessary
+        should_wait_for_vespa_sync: bool = True,
     ) -> None:
         """after: The task register time must be after this time."""
+        doc_synced = False
+        group_synced = False
         start = time.monotonic()
         while True:
-            last_synced = CCPairManager.get_sync_task(cc_pair, user_performing_action)
-            if last_synced and last_synced > after:
-                print(f"last_synced: {last_synced}")
+            # We are treating both syncs as part of one larger permission sync job
+            doc_last_synced = CCPairManager.get_doc_sync_task(
+                cc_pair, user_performing_action
+            )
+            group_last_synced = CCPairManager.get_group_sync_task(
+                cc_pair, user_performing_action
+            )
+
+            if not doc_synced and doc_last_synced and doc_last_synced > after:
+                print(f"doc_last_synced: {doc_last_synced}")
                 print(f"sync command start time: {after}")
                 print(f"permission sync complete: cc_pair={cc_pair.id}")
+                doc_synced = True
+
+            if not group_synced and group_last_synced and group_last_synced > after:
+                print(f"group_last_synced: {group_last_synced}")
+                print(f"sync command start time: {after}")
+                print(f"group sync complete: cc_pair={cc_pair.id}")
+                group_synced = True
+
+            if doc_synced and (group_synced or not should_wait_for_group_sync):
                 break
 
             elapsed = time.monotonic() - start
@@ -524,6 +577,9 @@ class CCPairManager:
         # this shouldnt be necessary but something is off with the timing for the sync jobs
         time.sleep(5)
 
+        if not should_wait_for_vespa_sync:
+            return
+
         print("waiting for vespa sync")
         # wait for the vespa sync to complete once the permission sync is complete
         start = time.monotonic()

backend/tests/integration/connector_job_tests/google/google_drive_api_utils.py

@@ -0,0 +1,186 @@
+from typing import Any
+from uuid import uuid4
+
+from google.oauth2.service_account import Credentials
+
+from onyx.connectors.google_utils.resources import get_drive_service
+from onyx.connectors.google_utils.resources import get_google_docs_service
+from onyx.connectors.google_utils.resources import GoogleDocsService
+from onyx.connectors.google_utils.resources import GoogleDriveService
+
+
+GOOGLE_SCOPES = {
+    "google_drive": [
+        "https://www.googleapis.com/auth/drive",
+        "https://www.googleapis.com/auth/admin.directory.group",
+        "https://www.googleapis.com/auth/admin.directory.user",
+    ],
+}
+
+
+def _create_doc_service(drive_service: GoogleDriveService) -> GoogleDocsService:
+    docs_service = get_google_docs_service(
+        creds=drive_service._http.credentials,
+        user_email=drive_service._http.credentials._subject,
+    )
+    return docs_service
+
+
+class GoogleDriveManager:
+    @staticmethod
+    def create_impersonated_drive_service(
+        service_account_key: dict, impersonated_user_email: str
+    ) -> GoogleDriveService:
+        """Gets a drive service that impersonates a specific user"""
+        credentials = Credentials.from_service_account_info(
+            service_account_key,
+            scopes=GOOGLE_SCOPES["google_drive"],
+            subject=impersonated_user_email,
+        )
+
+        service = get_drive_service(credentials, impersonated_user_email)
+
+        # Verify impersonation
+        about = service.about().get(fields="user").execute()
+        if about.get("user", {}).get("emailAddress") != impersonated_user_email:
+            raise ValueError(
+                f"Failed to impersonate {impersonated_user_email}. "
+                f"Instead got {about.get('user', {}).get('emailAddress')}"
+            )
+        return service
+
+    @staticmethod
+    def create_shared_drive(
+        drive_service: GoogleDriveService, admin_email: str, test_id: str
+    ) -> str:
+        """
+        Creates a shared drive and returns the drive's ID
+        """
+        try:
+            about = drive_service.about().get(fields="user").execute()
+            creating_user = about["user"]["emailAddress"]
+
+            # Verify we're still impersonating the admin
+            if creating_user != admin_email:
+                raise ValueError(
+                    f"Expected to create drive as {admin_email}, but instead created drive as {creating_user}"
+                )
+
+            drive_metadata = {"name": f"perm_sync_drive_{test_id}"}
+
+            request_id = str(uuid4())
+            drive = (
+                drive_service.drives()
+                .create(
+                    body=drive_metadata,
+                    requestId=request_id,
+                    fields="id,name,capabilities",
+                )
+                .execute()
+            )
+
+            return drive["id"]
+        except Exception as e:
+            print(f"Error creating shared drive: {str(e)}")
+            raise
+
+    @staticmethod
+    def create_empty_doc(
+        drive_service: Any,
+        drive_id: str,
+    ) -> str:
+        """
+        Creates an empty document in the given drive and returns the document's ID
+        """
+        file_metadata = {
+            "name": f"perm_sync_doc_{drive_id}_{str(uuid4())}",
+            "mimeType": "application/vnd.google-apps.document",
+            "parents": [drive_id],
+        }
+        file = (
+            drive_service.files()
+            .create(body=file_metadata, supportsAllDrives=True)
+            .execute()
+        )
+
+        return file["id"]
+
+    @staticmethod
+    def append_text_to_doc(
+        drive_service: GoogleDriveService, doc_id: str, text: str
+    ) -> None:
+        docs_service = _create_doc_service(drive_service)
+
+        docs_service.documents().batchUpdate(
+            documentId=doc_id,
+            body={
+                "requests": [{"insertText": {"location": {"index": 1}, "text": text}}]
+            },
+        ).execute()
+
+    @staticmethod
+    def update_file_permissions(
+        drive_service: Any, file_id: str, email: str, role: str = "reader"
+    ) -> None:
+        permission = {"type": "user", "role": role, "emailAddress": email}
+        drive_service.permissions().create(
+            fileId=file_id,
+            body=permission,
+            supportsAllDrives=True,
+            sendNotificationEmail=False,
+        ).execute()
+
+    @staticmethod
+    def remove_file_permissions(drive_service: Any, file_id: str, email: str) -> None:
+        permissions = (
+            drive_service.permissions()
+            .list(fileId=file_id, supportsAllDrives=True)
+            .execute()
+        )
+        # TODO: This is a hacky way to remove permissions. Removes anyone with reader role.
+        # Need to find a way to map a user's email to a permission id.
+        # The permissions.get returns a permissionID but email field is None,
+        # something to do with it being a group or domain wide delegation.
+        for permission in permissions.get("permissions", []):
+            if permission.get("role") == "reader":
+                drive_service.permissions().delete(
+                    fileId=file_id,
+                    permissionId=permission["id"],
+                    supportsAllDrives=True,
+                ).execute()
+                break
+
+    @staticmethod
+    def make_file_public(drive_service: Any, file_id: str) -> None:
+        permission = {"type": "anyone", "role": "reader"}
+        drive_service.permissions().create(
+            fileId=file_id, body=permission, supportsAllDrives=True
+        ).execute()
+
+    @staticmethod
+    def cleanup_drive(drive_service: Any, drive_id: str) -> None:
+        try:
+            # Delete up to 2 files that match our pattern
+            file_name_prefix = f"perm_sync_doc_{drive_id}"
+            files = (
+                drive_service.files()
+                .list(
+                    q=f"name contains '{file_name_prefix}'",
+                    driveId=drive_id,
+                    includeItemsFromAllDrives=True,
+                    supportsAllDrives=True,
+                    corpora="drive",
+                    fields="files(id)",
+                )
+                .execute()
+            )
+
+            for file in files.get("files", []):
+                drive_service.files().delete(
+                    fileId=file["id"], supportsAllDrives=True
+                ).execute()
+
+            # Then delete the drive
+            drive_service.drives().delete(driveId=drive_id).execute()
+        except Exception as e:
+            print(f"Error cleaning up drive {drive_id}: {e}")

backend/tests/integration/connector_job_tests/google/test_permission_sync.py

@@ -0,0 +1,332 @@
+import json
+import os
+from collections.abc import Generator
+from datetime import datetime
+from datetime import timezone
+from uuid import uuid4
+
+import pytest
+
+from onyx.configs.constants import DocumentSource
+from onyx.connectors.google_utils.resources import GoogleDriveService
+from onyx.connectors.google_utils.shared_constants import (
+    DB_CREDENTIALS_DICT_SERVICE_ACCOUNT_KEY,
+)
+from onyx.connectors.google_utils.shared_constants import (
+    DB_CREDENTIALS_PRIMARY_ADMIN_KEY,
+)
+from onyx.connectors.models import InputType
+from onyx.db.enums import AccessType
+from tests.integration.common_utils.managers.cc_pair import CCPairManager
+from tests.integration.common_utils.managers.connector import ConnectorManager
+from tests.integration.common_utils.managers.credential import CredentialManager
+from tests.integration.common_utils.managers.document_search import (
+    DocumentSearchManager,
+)
+from tests.integration.common_utils.managers.llm_provider import LLMProviderManager
+from tests.integration.common_utils.managers.user import UserManager
+from tests.integration.common_utils.test_models import DATestCCPair
+from tests.integration.common_utils.test_models import DATestConnector
+from tests.integration.common_utils.test_models import DATestCredential
+from tests.integration.common_utils.test_models import DATestUser
+from tests.integration.common_utils.vespa import vespa_fixture
+from tests.integration.connector_job_tests.google.google_drive_api_utils import (
+    GoogleDriveManager,
+)
+
+
+@pytest.fixture()
+def google_drive_test_env_setup() -> (
+    Generator[
+        tuple[
+            GoogleDriveService, str, DATestCCPair, DATestUser, DATestUser, DATestUser
+        ],
+        None,
+        None,
+    ]
+):
+    # Creating an admin user (first user created is automatically an admin)
+    admin_user: DATestUser = UserManager.create(email="admin@onyx-test.com")
+    # Creating a non-admin user
+    test_user_1: DATestUser = UserManager.create(email="test_user_1@onyx-test.com")
+    # Creating a non-admin user
+    test_user_2: DATestUser = UserManager.create(email="test_user_2@onyx-test.com")
+
+    service_account_key = os.environ["FULL_CONTROL_DRIVE_SERVICE_ACCOUNT"]
+    drive_id: str | None = None
+
+    try:
+        credentials = {
+            DB_CREDENTIALS_PRIMARY_ADMIN_KEY: admin_user.email,
+            DB_CREDENTIALS_DICT_SERVICE_ACCOUNT_KEY: service_account_key,
+        }
+
+        # Setup Google Drive
+        drive_service = GoogleDriveManager.create_impersonated_drive_service(
+            json.loads(service_account_key), admin_user.email
+        )
+        test_id = str(uuid4())
+        drive_id = GoogleDriveManager.create_shared_drive(
+            drive_service, admin_user.email, test_id
+        )
+
+        # Setup Onyx infrastructure
+        LLMProviderManager.create(user_performing_action=admin_user)
+
+        before = datetime.now(timezone.utc)
+        credential: DATestCredential = CredentialManager.create(
+            source=DocumentSource.GOOGLE_DRIVE,
+            credential_json=credentials,
+            user_performing_action=admin_user,
+        )
+        connector: DATestConnector = ConnectorManager.create(
+            name="Google Drive Test",
+            input_type=InputType.POLL,
+            source=DocumentSource.GOOGLE_DRIVE,
+            connector_specific_config={
+                "shared_drive_urls": f"https://drive.google.com/drive/folders/{drive_id}"
+            },
+            access_type=AccessType.SYNC,
+            user_performing_action=admin_user,
+        )
+        cc_pair: DATestCCPair = CCPairManager.create(
+            credential_id=credential.id,
+            connector_id=connector.id,
+            access_type=AccessType.SYNC,
+            user_performing_action=admin_user,
+        )
+        CCPairManager.wait_for_indexing_completion(
+            cc_pair=cc_pair, after=before, user_performing_action=admin_user
+        )
+
+        yield drive_service, drive_id, cc_pair, admin_user, test_user_1, test_user_2
+
+    except json.JSONDecodeError:
+        pytest.skip("FULL_CONTROL_DRIVE_SERVICE_ACCOUNT is not valid JSON")
+    finally:
+        # Cleanup drive and file
+        if drive_id is not None:
+            GoogleDriveManager.cleanup_drive(drive_service, drive_id)
+
+
+@pytest.mark.xfail(reason="Needs to be tested for flakiness")
+def test_google_permission_sync(
+    reset: None,
+    vespa_client: vespa_fixture,
+    google_drive_test_env_setup: tuple[
+        GoogleDriveService, str, DATestCCPair, DATestUser, DATestUser, DATestUser
+    ],
+) -> None:
+    (
+        drive_service,
+        drive_id,
+        cc_pair,
+        admin_user,
+        test_user_1,
+        test_user_2,
+    ) = google_drive_test_env_setup
+
+    # ----------------------BASELINE TEST----------------------
+    before = datetime.now(timezone.utc)
+
+    # Create empty test doc in drive
+    doc_id_1 = GoogleDriveManager.create_empty_doc(drive_service, drive_id)
+
+    # Append text to doc
+    doc_text_1 = "The secret number is 12345"
+    GoogleDriveManager.append_text_to_doc(drive_service, doc_id_1, doc_text_1)
+
+    # run indexing
+    CCPairManager.run_once(cc_pair, admin_user)
+    CCPairManager.wait_for_indexing_completion(
+        cc_pair=cc_pair, after=before, user_performing_action=admin_user
+    )
+
+    # run permission sync
+    CCPairManager.sync(
+        cc_pair=cc_pair,
+        user_performing_action=admin_user,
+    )
+    CCPairManager.wait_for_sync(
+        cc_pair=cc_pair,
+        after=before,
+        number_of_updated_docs=1,
+        user_performing_action=admin_user,
+    )
+
+    # Verify admin has access to document
+    admin_results = DocumentSearchManager.search_documents(
+        query="secret number", user_performing_action=admin_user
+    )
+    assert doc_text_1 in [result.strip("\ufeff") for result in admin_results]
+
+    # Verify test_user_1 cannot access document
+    user1_results = DocumentSearchManager.search_documents(
+        query="secret number", user_performing_action=test_user_1
+    )
+    assert doc_text_1 not in [result.strip("\ufeff") for result in user1_results]
+
+    # ----------------------GRANT USER 1 DOC PERMISSIONS TEST--------------------------
+    before = datetime.now(timezone.utc)
+
+    # Grant user 1 access to document 1
+    GoogleDriveManager.update_file_permissions(
+        drive_service=drive_service,
+        file_id=doc_id_1,
+        email=test_user_1.email,
+        role="reader",
+    )
+
+    # Create a second doc in the drive which user 1 should not have access to
+    doc_id_2 = GoogleDriveManager.create_empty_doc(drive_service, drive_id)
+    doc_text_2 = "The secret number is 67890"
+    GoogleDriveManager.append_text_to_doc(drive_service, doc_id_2, doc_text_2)
+
+    # Run indexing
+    CCPairManager.run_once(cc_pair, admin_user)
+    CCPairManager.wait_for_indexing_completion(
+        cc_pair=cc_pair,
+        after=before,
+        user_performing_action=admin_user,
+    )
+
+    # Run permission sync
+    CCPairManager.sync(
+        cc_pair=cc_pair,
+        user_performing_action=admin_user,
+    )
+    CCPairManager.wait_for_sync(
+        cc_pair=cc_pair,
+        after=before,
+        number_of_updated_docs=1,
+        user_performing_action=admin_user,
+    )
+
+    # Verify admin can access both documents
+    admin_results = DocumentSearchManager.search_documents(
+        query="secret number", user_performing_action=admin_user
+    )
+    assert {doc_text_1, doc_text_2} == {
+        result.strip("\ufeff") for result in admin_results
+    }
+
+    # Verify user 1 can access document 1
+    user1_results = DocumentSearchManager.search_documents(
+        query="secret number", user_performing_action=test_user_1
+    )
+    assert doc_text_1 in [result.strip("\ufeff") for result in user1_results]
+
+    # Verify user 1 cannot access document 2
+    user1_results_2 = DocumentSearchManager.search_documents(
+        query="secret number", user_performing_action=test_user_1
+    )
+    assert doc_text_2 not in [result.strip("\ufeff") for result in user1_results_2]
+
+    # ----------------------REMOVE USER 1 DOC PERMISSIONS TEST--------------------------
+    before = datetime.now(timezone.utc)
+
+    # Remove user 1 access to document 1
+    GoogleDriveManager.remove_file_permissions(
+        drive_service=drive_service, file_id=doc_id_1, email=test_user_1.email
+    )
+    # Run permission sync
+    CCPairManager.sync(
+        cc_pair=cc_pair,
+        user_performing_action=admin_user,
+    )
+    CCPairManager.wait_for_sync(
+        cc_pair=cc_pair,
+        after=before,
+        number_of_updated_docs=1,
+        user_performing_action=admin_user,
+    )
+
+    # Verify admin can access both documents
+    admin_results = DocumentSearchManager.search_documents(
+        query="secret number", user_performing_action=admin_user
+    )
+    assert {doc_text_1, doc_text_2} == {
+        result.strip("\ufeff") for result in admin_results
+    }
+
+    # Verify user 1 cannot access either document
+    user1_results = DocumentSearchManager.search_documents(
+        query="secret numbers", user_performing_action=test_user_1
+    )
+    assert {result.strip("\ufeff") for result in user1_results} == set()
+
+    # ----------------------GRANT USER 1 DRIVE PERMISSIONS TEST--------------------------
+    before = datetime.now(timezone.utc)
+
+    # Grant user 1 access to drive
+    GoogleDriveManager.update_file_permissions(
+        drive_service=drive_service,
+        file_id=drive_id,
+        email=test_user_1.email,
+        role="reader",
+    )
+
+    # Run permission sync
+    CCPairManager.sync(
+        cc_pair=cc_pair,
+        user_performing_action=admin_user,
+    )
+
+    CCPairManager.wait_for_sync(
+        cc_pair=cc_pair,
+        after=before,
+        number_of_updated_docs=2,
+        user_performing_action=admin_user,
+        # if we are only updating the group definition for this test we use this varaiable,
+        # since it doesn't result in a vespa sync so we don't want to wait for it
+        should_wait_for_vespa_sync=False,
+    )
+
+    # Verify user 1 can access both documents
+    user1_results = DocumentSearchManager.search_documents(
+        query="secret numbers", user_performing_action=test_user_1
+    )
+    assert {doc_text_1, doc_text_2} == {
+        result.strip("\ufeff") for result in user1_results
+    }
+
+    # ----------------------MAKE DRIVE PUBLIC TEST--------------------------
+    before = datetime.now(timezone.utc)
+
+    # Unable to make drive itself public as Google's security policies prevent this, so we make the documents public instead
+    GoogleDriveManager.make_file_public(drive_service, doc_id_1)
+    GoogleDriveManager.make_file_public(drive_service, doc_id_2)
+
+    # Run permission sync
+    CCPairManager.sync(
+        cc_pair=cc_pair,
+        user_performing_action=admin_user,
+    )
+    CCPairManager.wait_for_sync(
+        cc_pair=cc_pair,
+        after=before,
+        number_of_updated_docs=2,
+        user_performing_action=admin_user,
+    )
+
+    # Verify all users can access both documents
+    admin_results = DocumentSearchManager.search_documents(
+        query="secret number", user_performing_action=admin_user
+    )
+    assert {doc_text_1, doc_text_2} == {
+        result.strip("\ufeff") for result in admin_results
+    }
+
+    user1_results = DocumentSearchManager.search_documents(
+        query="secret number", user_performing_action=test_user_1
+    )
+    assert {doc_text_1, doc_text_2} == {
+        result.strip("\ufeff") for result in user1_results
+    }
+
+    user2_results = DocumentSearchManager.search_documents(
+        query="secret number", user_performing_action=test_user_2
+    )
+    assert {doc_text_1, doc_text_2} == {
+        result.strip("\ufeff") for result in user2_results
+    }