From c03ce8cdb2e7849361ea50db888b7e3080eaafcd Mon Sep 17 00:00:00 2001
From: "copilot-swe-agent[bot]" <198982749+Copilot@users.noreply.github.com>
Date: Mon, 23 Mar 2026 21:32:44 +0000
Subject: [PATCH] test(main,imap): fix failing IMAP tests and add coverage for
 shutdown exception paths

Co-authored-by: christianlouis <361235+christianlouis@users.noreply.github.com>
Agent-Logs-Url: https://github.com/christianlouis/DocuElevate/sessions/05be730d-fcbd-43a5-98be-26d853cf57d0
---
 tests/test_api_imap_accounts.py | 15 ++++++++--
 tests/test_main.py              | 52 +++++++++++++++++++++++++++++++++
 2 files changed, 64 insertions(+), 3 deletions(-)

diff --git a/tests/test_api_imap_accounts.py b/tests/test_api_imap_accounts.py
index d872547b..90381cdc 100644
--- a/tests/test_api_imap_accounts.py
+++ b/tests/test_api_imap_accounts.py
@@ -524,7 +524,10 @@ class TestTestImapConnection:
         from app.api.imap_accounts import _test_imap_connection
 
         mock_mail = MagicMock()
-        with patch("imaplib.IMAP4_SSL", return_value=mock_mail):
+        with (
+            patch("app.api.imap_accounts.is_private_ip", return_value=False),
+            patch("imaplib.IMAP4_SSL", return_value=mock_mail),
+        ):
             result = _test_imap_connection(
                 "imap.example.com",
                 993,
@@ -541,7 +544,10 @@ class TestTestImapConnection:
         """An exception raised by IMAP4_SSL returns success=False."""
         from app.api.imap_accounts import _test_imap_connection
 
-        with patch("imaplib.IMAP4_SSL", side_effect=Exception("auth failed")):
+        with (
+            patch("app.api.imap_accounts.is_private_ip", return_value=False),
+            patch("imaplib.IMAP4_SSL", side_effect=Exception("auth failed")),
+        ):
             result = _test_imap_connection(
                 "imap.example.com",
                 993,
@@ -557,7 +563,10 @@ class TestTestImapConnection:
         """An OSError returns success=False with a network error message."""
         from app.api.imap_accounts import _test_imap_connection
 
-        with patch("imaplib.IMAP4", side_effect=OSError("connection refused")):
+        with (
+            patch("app.api.imap_accounts.is_private_ip", return_value=False),
+            patch("imaplib.IMAP4", side_effect=OSError("connection refused")),
+        ):
             result = _test_imap_connection(
                 "bad-host",
                 143,
diff --git a/tests/test_main.py b/tests/test_main.py
index b59c2c93..015c499f 100644
--- a/tests/test_main.py
+++ b/tests/test_main.py
@@ -145,6 +145,58 @@ class TestLifespanEvents:
             # load_settings_from_db must also have been called
             mock_load_settings.assert_called_once()
 
+    @pytest.mark.asyncio
+    async def test_lifespan_shutdown_logging_exception_is_silenced(self):
+        """Exceptions raised by logging.info during shutdown are silently ignored."""
+
+        def _raise_on_shutdown(msg, *args, **kwargs):
+            if "shutting down" in str(msg):
+                raise OSError("stream closed")
+
+        with (
+            patch("app.database.init_db"),
+            patch("app.database.SessionLocal") as mock_session_cls,
+            patch("app.utils.config_loader.load_settings_from_db"),
+            patch("app.utils.config_validator.dump_all_settings"),
+            patch("app.utils.config_validator.check_all_configs", return_value={"email": [], "storage": {}}),
+            patch("app.utils.notification.init_apprise"),
+            patch("app.utils.notification.notify_startup"),
+            patch("app.utils.notification.notify_shutdown"),
+            patch("app.main.init_sentry"),
+            patch("app.main.logging.info", side_effect=_raise_on_shutdown),
+        ):
+            mock_db = MagicMock()
+            mock_session_cls.return_value = mock_db
+
+            from app.main import app, lifespan
+
+            # Should complete without raising despite the logging error
+            async with lifespan(app):
+                pass
+
+    @pytest.mark.asyncio
+    async def test_lifespan_shutdown_notify_exception_is_silenced(self):
+        """Exceptions raised by notify_shutdown during shutdown are silently ignored."""
+        with (
+            patch("app.database.init_db"),
+            patch("app.database.SessionLocal") as mock_session_cls,
+            patch("app.utils.config_loader.load_settings_from_db"),
+            patch("app.utils.config_validator.dump_all_settings"),
+            patch("app.utils.config_validator.check_all_configs", return_value={"email": [], "storage": {}}),
+            patch("app.utils.notification.init_apprise"),
+            patch("app.utils.notification.notify_startup"),
+            patch("app.main.notify_shutdown", side_effect=OSError("stream closed")),
+            patch("app.main.init_sentry"),
+        ):
+            mock_db = MagicMock()
+            mock_session_cls.return_value = mock_db
+
+            from app.main import app, lifespan
+
+            # Should complete without raising despite the notify_shutdown error
+            async with lifespan(app):
+                pass
+
 
 @pytest.mark.unit
 class TestExceptionHandlers: