From 998b2e2121480b2c9cebedc0cb9901cfe83307f6 Mon Sep 17 00:00:00 2001
From: Nate Harris <nwithan8@users.noreply.github.com>
Date: Thu, 21 Aug 2025 00:21:11 -0600
Subject: [PATCH] - Fix unit tests for hook email trigger conditional based on
 end date

---
 radicale/hook/email/__init__.py   | 11 +++++---
 radicale/tests/test_hook_email.py | 46 +++++++++++++++----------------
 2 files changed, 29 insertions(+), 28 deletions(-)

diff --git a/radicale/hook/email/__init__.py b/radicale/hook/email/__init__.py
index 62bf3195..2defaa95 100644
--- a/radicale/hook/email/__init__.py
+++ b/radicale/hook/email/__init__.py
@@ -981,10 +981,13 @@ class Hook(BaseHook):
                 return
             email_event_end_time = email_event_event.datetime_end  # type: ignore
             # Skip notification if the event end time is more than 1 minute in the past.
-            if email_event_end_time and email_event_end_time.time and email_event_end_time.time < (
-                    datetime.now() - timedelta(minutes=1)):
-                logger.warning("Event end time is in the past, skipping notification for event: %s",
-                               email_event_event.uid)
+            if email_event_end_time and email_event_end_time.time:
+                event_end = email_event_end_time.time  # type: ignore
+                now = datetime.now(
+                    event_end.tzinfo) if event_end.tzinfo else datetime.now()  # Handle timezone-aware datetime
+                if event_end < (now - timedelta(minutes=1)):
+                    logger.warning("Event end time is in the past, skipping notification for event: %s",
+                                   email_event_event.uid)
                 return
 
             if not previous_item_str:
diff --git a/radicale/tests/test_hook_email.py b/radicale/tests/test_hook_email.py
index af012a6c..b7fef935 100644
--- a/radicale/tests/test_hook_email.py
+++ b/radicale/tests/test_hook_email.py
@@ -93,16 +93,12 @@ permissions: RrWw""")
         assert "VEVENT" in answer
         assert "Event" in answer
         assert "UID:event" in answer
-        found = 0
-        for line in caplog.messages:
-            if line.find("notification_item: {'type': 'upsert'") != -1:
-                found = found | 1
-            if line.find("to_addresses=['janedoe@example.com']") != -1:
-                found = found | 2
-            if line.find("to_addresses=['johndoe@example.com']") != -1:
-                found = found | 4
-        if (found != 7):
-            raise ValueError("Logging misses expected log lines, found=%d", found)
+
+        logs = caplog.messages
+        # Should have a log saying the notification item was received
+        assert len([log for log in logs if "received notification_item: {'type': 'upsert'," in log]) == 1
+        # Should NOT have a log saying that no email is sent (email won't actually be sent due to dryrun)
+        assert len([log for log in logs if "skipping notification for event: event1" in log]) == 0
 
     def test_add_event_with_past_end_date(self, caplog) -> None:
         caplog.set_level(logging.WARNING)
@@ -119,8 +115,11 @@ permissions: RrWw""")
         assert "Event" in answer
         assert "UID:event" in answer
 
-        # Should not trigger an email
-        assert len(caplog.messages) == 0
+        logs = caplog.messages
+        # Should have a log saying the notification item was received
+        assert len([log for log in logs if "received notification_item: {'type': 'upsert'," in log]) == 1
+        # Should have a log saying that no email is sent due to past end date
+        assert len([log for log in logs if "Event end time is in the past, skipping notification for event: event1" in log]) == 1
 
     def test_delete_event_with_future_end_date(self, caplog) -> None:
         caplog.set_level(logging.WARNING)
@@ -134,16 +133,12 @@ permissions: RrWw""")
         assert responses[path] == 200
         _, answer = self.get("/calendar.ics/")
         assert "VEVENT" not in answer
-        found = 0
-        for line in caplog.messages:
-            if line.find("notification_item: {'type': 'delete'") != -1:
-                found = found | 1
-            if line.find("to_addresses=['janedoe@example.com']") != -1:
-                found = found | 2
-            if line.find("to_addresses=['johndoe@example.com']") != -1:
-                found = found | 4
-        if (found != 7):
-            raise ValueError("Logging misses expected log lines, found=%d", found)
+
+        logs = caplog.messages
+        # Should have a log saying the notification item was received
+        assert len([log for log in logs if "received notification_item: {'type': 'delete'," in log]) == 1
+        # Should NOT have a log saying that no email is sent (email won't actually be sent due to dryrun)
+        assert len([log for log in logs if "skipping notification for event: event1" in log]) == 0
 
     def test_delete_event_with_past_end_date(self, caplog) -> None:
         caplog.set_level(logging.WARNING)
@@ -158,5 +153,8 @@ permissions: RrWw""")
         _, answer = self.get("/calendar.ics/")
         assert "VEVENT" not in answer
 
-        # Should not trigger an email
-        assert len(caplog.messages) == 0
+        logs = caplog.messages
+        # Should have a log saying the notification item was received
+        assert len([log for log in logs if "received notification_item: {'type': 'delete'," in log]) == 1
+        # Should have a log saying that no email is sent due to past end date
+        assert len([log for log in logs if "Event end time is in the past, skipping notification for event: event1" in log]) == 1