[Outlook] Feature: Office365 multi-user support

Introduced BaseOffice365User abstract base class to standardize Office 365 user handling.
Added MultiOffice365Users to manage multiple emails from config.
Added client_emails (comma-separated) in OutlookDataSource config.
Resolved issue with fetching too many users causing SMTP server not found error.

connectors/sources/outlook.py

@@ -7,9 +7,11 @@
 
 import asyncio
 import os
+from abc import ABC, abstractmethod
 from copy import copy
 from datetime import date
 from functools import cached_property, partial
+from typing import List
 
 import aiofiles
 import aiohttp
@@ -348,13 +350,13 @@ async def get_user_accounts(self):
             yield user_account
 
 
-class Office365Users:
-    """Fetch users from Office365 Active Directory"""
+class BaseOffice365User(ABC):
+    """Abstract base class for Office 365 user management"""
 
     def __init__(self, client_id, client_secret, tenant_id):
-        self.tenant_id = tenant_id
         self.client_id = client_id
         self.client_secret = client_secret
+        self.tenant_id = tenant_id
 
     @cached_property
     def _get_session(self):
@@ -403,6 +405,21 @@ async def _fetch_token(self):
         except Exception as exception:
             self._check_errors(response=exception)
 
+    @abstractmethod
+    async def get_users(self):
+        pass
+
+    @abstractmethod
+    async def get_user_accounts(self):
+        pass 
+
+
+class Office365Users(BaseOffice365User):
+    """Fetch users from Office365 Active Directory"""
+
+    def __init__(self, client_id, client_secret, tenant_id):
+        super().__init__(client_id, client_secret, tenant_id)
+
     @retryable(
         retries=RETRIES,
         interval=RETRY_INTERVAL,
@@ -456,6 +473,57 @@ async def get_user_accounts(self):
                 yield user_account
 
 
+class MultiOffice365Users(BaseOffice365User):
+    """Fetch multiple Office365 users based on a list of email addresses."""
+
+    def __init__(self, client_id, client_secret, tenant_id, client_emails: List[str]):
+        super().__init__(client_id, client_secret, tenant_id)
+        self.client_emails = client_emails
+
+    async def get_users(self):
+        access_token = await self._fetch_token()
+        for email in self.client_emails:
+            url = f"https://graph.microsoft.com/v1.0/users/{email}"
+            try:
+                async with self._get_session.get(
+                    url=url,
+                    headers={
+                        "Authorization": f"Bearer {access_token}",
+                        "Content-Type": "application/json",
+                    },
+                ) as response:
+                    json_response = await response.json()
+                    yield json_response
+            except Exception:
+                raise
+
+    async def get_user_accounts(self):
+        async for user in self.get_users():
+            mail = user.get("mail")
+            if mail is None:
+                continue
+
+            credentials = OAuth2Credentials(
+                client_id=self.client_id,
+                tenant_id=self.tenant_id,
+                client_secret=self.client_secret,
+                identity=Identity(primary_smtp_address=mail),
+            )
+            configuration = Configuration(
+                credentials=credentials,
+                auth_type=OAUTH2,
+                service_endpoint=EWS_ENDPOINT,
+                retry_policy=FaultTolerance(max_wait=120),
+            )
+            user_account = Account(
+                primary_smtp_address=mail,
+                config=configuration,
+                autodiscover=False,
+                access_type=IMPERSONATION,
+            )
+            yield user_account
+
+
 class OutlookDocFormatter:
     """Format Outlook object documents to Elasticsearch document"""
 
@@ -583,6 +651,27 @@ def attachment_doc_formatter(self, attachment, attachment_type, timezone):
         }
 
 
+class UserFactory:
+    """Factory class for creating Office365 user instances"""
+
+    @staticmethod
+    def create_user(configuration: dict) -> BaseOffice365User:
+        if configuration.get("client_emails"):
+            client_emails = [email.strip() for email in configuration["client_emails"].split(",")]
+            return MultiOffice365Users(
+                client_id=configuration["client_id"],
+                client_secret=configuration["client_secret"],
+                tenant_id=configuration["tenant_id"],
+                client_emails=client_emails
+            )
+        else:
+            return Office365Users(
+                client_id=configuration["client_id"],
+                client_secret=configuration["client_secret"],
+                tenant_id=configuration["tenant_id"]
+            )
+
+
 class OutlookClient:
     """Outlook client to handle API calls made to Outlook"""
 
@@ -605,11 +694,7 @@ def set_logger(self, logger_):
     @cached_property
     def _get_user_instance(self):
         if self.is_cloud:
-            return Office365Users(
-                client_id=self.configuration["client_id"],
-                client_secret=self.configuration["client_secret"],
-                tenant_id=self.configuration["tenant_id"],
-            )
+            return UserFactory.create_user(self.configuration)
 
         return ExchangeUsers(
             ad_server=self.configuration["active_directory_server"],
@@ -666,9 +751,12 @@ async def get_tasks(self, account):
             yield task
 
     async def get_contacts(self, account):
-        folder = account.root / "Top of Information Store" / "Contacts"
-        for contact in await asyncio.to_thread(folder.all().only, *CONTACT_FIELDS):
-            yield contact
+        try:
+            folder = account.root / "Top of Information Store" / "Contacts"
+            for contact in await asyncio.to_thread(folder.all().only, *CONTACT_FIELDS):
+                yield contact
+        except Exception:
+            raise
 
 
 class OutlookDataSource(BaseDataSource):
@@ -735,6 +823,13 @@ def get_default_configuration(cls):
                 "sensitive": True,
                 "type": "str",
             },
+            "client_emails": {
+                "depends_on": [{"field": "data_source", "value": OUTLOOK_CLOUD}],
+                "label": "Client Email Addresses (comma-separated)",
+                "order": 5,
+                "required": False,
+                "type": "str",
+            },
             "exchange_server": {
                 "depends_on": [{"field": "data_source", "value": OUTLOOK_SERVER}],
                 "label": "Exchange Server",
@@ -1072,9 +1167,11 @@ async def get_docs(self, filtering=None):
             dictionary: dictionary containing meta-data of the files.
         """
         async for account in self.client._get_user_instance.get_user_accounts():
+            self._logger.debug(f"Processing account: {account}")
             timezone = account.default_timezone or DEFAULT_TIMEZONE
 
             async for mail in self._fetch_mails(account=account, timezone=timezone):
+                self._logger.debug(f"Fetched mail: {mail}")
                 yield mail
 
             async for contact in self._fetch_contacts(

tests/sources/test_outlook.py

@@ -374,6 +374,7 @@ async def create_outlook_source(
     tenant_id="foo",
     client_id="bar",
     client_secret="faa",
+    client_emails=None,
     exchange_server="127.0.0.1",
     active_directory_server="127.0.0.1",
     username="fee",
@@ -383,12 +384,16 @@ async def create_outlook_source(
     ssl_ca="",
     use_text_extraction_service=False,
 ):
+    if client_emails is None:
+        client_emails = ""
+
     async with create_source(
         OutlookDataSource,
         data_source=data_source,
         tenant_id=tenant_id,
         client_id=client_id,
         client_secret=client_secret,
+        client_emails=client_emails,
         exchange_server=exchange_server,
         active_directory_server=active_directory_server,
         username=username,
@@ -415,26 +420,36 @@ def get_stream_reader():
     return async_mock
 
 
-def side_effect_function(url, headers):
+def side_effect_function(client_emails=None):
     """Dynamically changing return values for API calls
     Args:
         url, ssl: Params required for get call
+        client_emails: Optional string of comma-separated email addresses
     """
-    if url == "https://graph.microsoft.com/v1.0/users?$top=999":
-        return get_json_mock(
-            mock_response={
-                "@odata.nextLink": "https://graph.microsoft.com/v1.0/users?$top=999&$skipToken=fake-skip-token",
-                "value": [{"mail": "[email protected]"}],
-            },
-            status=200,
-        )
-    elif (
-        url
-        == "https://graph.microsoft.com/v1.0/users?$top=999&$skipToken=fake-skip-token"
-    ):
-        return get_json_mock(
-            mock_response={"value": [{"mail": "[email protected]"}]}, status=200
-        )
+    def inner(url, headers):
+        if client_emails:
+            emails = [email.strip() for email in client_emails.split(",")]
+            for email in emails:
+                if url == f"https://graph.microsoft.com/v1.0/users/{email}":
+                    users_response = {"value": [{"mail": email}]}
+                    return get_json_mock(mock_response=users_response, status=200)
+        elif url == "https://graph.microsoft.com/v1.0/users?$top=999":
+            return get_json_mock(
+                mock_response={
+                    "@odata.nextLink": "https://graph.microsoft.com/v1.0/users?$top=999&$skipToken=fake-skip-token",
+                    "value": [{"mail": "[email protected]"}],
+                },
+                status=200,
+            )
+        elif (
+            url
+            == "https://graph.microsoft.com/v1.0/users?$top=999&$skipToken=fake-skip-token"
+        ):
+            return get_json_mock(
+                mock_response={"value": [{"mail": "[email protected]"}]}, status=200
+            )
+
+    return inner
 
 
 @pytest.mark.asyncio
@@ -459,6 +474,7 @@ def side_effect_function(url, headers):
                 "tenant_id": "foo",
                 "client_id": "bar",
                 "client_secret": "",
+                "client_emails": None,
             }
         ),
     ],
@@ -497,6 +513,17 @@ async def test_validate_configuration_with_invalid_dependency_fields_raises_erro
                 "tenant_id": "foo",
                 "client_id": "bar",
                 "client_secret": "foo.bar",
+                "client_emails": None
+            }
+        ),
+        (
+            # Outlook Cloud with non-blank dependent fields & client_emails provided
+            {
+                "data_source": OUTLOOK_CLOUD,
+                "tenant_id": "foo",
+                "client_id": "bar",
+                "client_secret": "foo.bar",
+                "client_emails": "[email protected]"
             }
         ),
     ],
@@ -552,7 +579,7 @@ async def test_ping_for_cloud():
         ):
             with mock.patch(
                 "aiohttp.ClientSession.get",
-                side_effect=side_effect_function,
+                side_effect=side_effect_function(),
             ):
                 await source.ping()
 
@@ -597,13 +624,49 @@ async def test_get_users_for_cloud():
         ):
             with mock.patch(
                 "aiohttp.ClientSession.get",
-                side_effect=side_effect_function,
+                side_effect=side_effect_function(),
             ):
                 async for response in source.client._get_user_instance.get_users():
                     user_mails = [user["mail"] for user in response["value"]]
                     users.extend(user_mails)
                 assert users == ["[email protected]", "[email protected]"]
 
+    client_emails = "[email protected]"
+    async with create_outlook_source(client_emails=client_emails) as source:
+        users = []
+        with mock.patch(
+            "aiohttp.ClientSession.post",
+            return_value=get_json_mock(
+                mock_response={"access_token": "fake-token"}, status=200
+            ),
+        ):
+            with mock.patch(
+                "aiohttp.ClientSession.get",
+                side_effect=side_effect_function(client_emails),
+            ):
+                async for response in source.client._get_user_instance.get_users():
+                    user_mails = [user["mail"] for user in response["value"]]
+                    users.extend(user_mails)
+                assert users == ["[email protected]"]
+
+    client_emails = "[email protected], [email protected]"
+    async with create_outlook_source(client_emails=client_emails) as source:
+        users = []
+        with mock.patch(
+            "aiohttp.ClientSession.post",
+            return_value=get_json_mock(
+                mock_response={"access_token": "fake-token"}, status=200
+            ),
+        ):
+            with mock.patch(
+                "aiohttp.ClientSession.get",
+                side_effect=side_effect_function(client_emails),
+            ):
+                async for response in source.client._get_user_instance.get_users():
+                    user_mails = [user["mail"] for user in response["value"]]
+                    users.extend(user_mails)
+                assert set(users) == {"[email protected]", "[email protected]"}
+
 
 @pytest.mark.asyncio
 @patch("connectors.sources.outlook.Connection")