From 311f226d448f7444629b8fcbe4c9e21620adbe06 Mon Sep 17 00:00:00 2001
From: Afonso Coutinho <afonso@omelhorsite.pt>
Date: Tue, 2 Jun 2026 17:03:58 +0100
Subject: [PATCH] fix: calendar check-in digest drops events 7-8 days out
 (#1249)

* fix: close 1-day gap in calendar digest windows (events ~7-8 days out)

* test: calendar digest windows are contiguous and cover 7-8 day events
---
 src/task_scheduler.py        | 20 +++++++++++++++-----
 tests/test_digest_windows.py | 22 ++++++++++++++++++++++
 2 files changed, 37 insertions(+), 5 deletions(-)
 create mode 100644 tests/test_digest_windows.py

diff --git a/src/task_scheduler.py b/src/task_scheduler.py
index d5b7a87..dbf389b 100644
--- a/src/task_scheduler.py
+++ b/src/task_scheduler.py
@@ -203,6 +203,20 @@ RETIRED_HOUSEKEEPING_ACTIONS = frozenset({
 })
 
 
+def _digest_windows(now):
+    """(label, start, end) buckets for the calendar check-in digest.
+
+    The windows are contiguous so no event is dropped between buckets — an
+    earlier version started the 30-day window at now+8d while the week window
+    ended at now+7d, so events ~7-8 days out fell into no bucket.
+    """
+    return [
+        ("today_tomorrow", now, now + timedelta(days=2)),
+        ("this_week", now + timedelta(days=2), now + timedelta(days=7)),
+        ("next_30_days", now + timedelta(days=7), now + timedelta(days=30)),
+    ]
+
+
 class TaskScheduler:
     def __init__(self, session_manager):
         self._session_manager = session_manager
@@ -1082,11 +1096,7 @@ class TaskScheduler:
             from core.database import SessionLocal as _SL, CalendarEvent as _CE
             _db = _SL()
             try:
-                for label, start, end in [
-                    ("today_tomorrow", now, now + timedelta(days=2)),
-                    ("this_week",      now + timedelta(days=2), now + timedelta(days=7)),
-                    ("next_30_days",   now + timedelta(days=8), now + timedelta(days=30)),
-                ]:
+                for label, start, end in _digest_windows(now):
                     # Strip timezone for naive DB comparison
                     _s = start.replace(tzinfo=None) if start.tzinfo else start
                     _e = end.replace(tzinfo=None) if end.tzinfo else end
diff --git a/tests/test_digest_windows.py b/tests/test_digest_windows.py
new file mode 100644
index 0000000..143306b
--- /dev/null
+++ b/tests/test_digest_windows.py
@@ -0,0 +1,22 @@
+"""Tests for the calendar check-in digest windows (src/task_scheduler.py)."""
+from datetime import datetime, timedelta
+
+from src.task_scheduler import _digest_windows
+
+
+def test_windows_are_contiguous_with_no_gap():
+    now = datetime(2026, 6, 2, 9, 0, 0)
+    windows = _digest_windows(now)
+    # Each window starts exactly where the previous ended — no gap between
+    # buckets (the old code jumped from now+7d to now+8d, dropping events).
+    for (prev, cur) in zip(windows, windows[1:]):
+        assert cur[1] == prev[2]
+    assert windows[0][1] == now
+    assert windows[-1][2] == now + timedelta(days=30)
+
+
+def test_event_seven_and_a_half_days_out_is_covered():
+    now = datetime(2026, 6, 2, 9, 0, 0)
+    event = now + timedelta(days=7, hours=12)  # fell in the old 7-8 day gap
+    buckets = [label for label, start, end in _digest_windows(now) if start <= event <= end]
+    assert buckets, "event ~7.5 days out should land in a digest window"