diff --git a/internal/time_range.go b/internal/time_range.go
index e52bf55bb..683a42f62 100644
--- a/internal/time_range.go
+++ b/internal/time_range.go
@@ -78,15 +78,12 @@ func NewWeekRangeInLocation(startTime, endTime TimeOfDay, startDay, endDay time.
 	return r, nil
 }
 
-func (r *TimeRange) isInTimeRange(t time.Time) bool {
-	t = t.In(r.loc)
-	ts := NewTimeOfDay(t.Clock()).d
-
+func (r *TimeRange) isInWeekdays(day time.Weekday) bool {
 	if len(r.weekdays) > 0 {
 		found := false
 
 		for _, weekday := range r.weekdays {
-			if t.Weekday() == weekday {
+			if day == weekday {
 				found = true
 				break
 			}
@@ -97,11 +94,34 @@ func (r *TimeRange) isInTimeRange(t time.Time) bool {
 		}
 	}
 
+	return true
+}
+
+func (r *TimeRange) addWeekdayOffset(day time.Weekday, offset int) time.Weekday {
+	return (day + time.Weekday(offset)) % 7
+}
+
+func (r *TimeRange) isInTimeRange(t time.Time) bool {
+	t = t.In(r.loc)
+	ts := NewTimeOfDay(t.Clock()).d
+
 	if r.startTime.d < r.endTime.d {
-		return r.startTime.d <= ts && ts <= r.endTime.d
+		if r.isInWeekdays(t.Weekday()) {
+			return r.startTime.d <= ts && ts <= r.endTime.d
+		}
+
+		return false
+	}
+
+	if ts <= r.endTime.d {
+		return r.isInWeekdays(r.addWeekdayOffset(t.Weekday(), -1))
+	}
+
+	if ts >= r.startTime.d {
+		return r.isInWeekdays(t.Weekday())
 	}
 
-	return !(r.endTime.d < ts && ts < r.startTime.d)
+	return false
 }
 
 func (r *TimeRange) isInWeekRange(t time.Time) bool {
diff --git a/internal/time_range_test.go b/internal/time_range_test.go
index 55740b113..c9d6a494f 100644
--- a/internal/time_range_test.go
+++ b/internal/time_range_test.go
@@ -245,6 +245,33 @@ func TestTimeRangeIsInRange(t *testing.T) {
 			now:             time.Date(2016, time.August, 10, 2, 0, 0, 0, time.UTC),
 			expectedInRange: false,
 		},
+		{
+			label:           "18:59:00 Sunday, crossing midnight",
+			start:           NewTimeOfDay(19, 0, 0),
+			end:             NewTimeOfDay(6, 0, 0),
+			weekdays:        []time.Weekday{time.Sunday},
+			location:        time.UTC,
+			now:             time.Date(2006, time.December, 3, 18, 59, 0, 0, time.UTC),
+			expectedInRange: false,
+		},
+		{
+			label:           "5:59AM Monday, crossing midnight",
+			start:           NewTimeOfDay(19, 0, 0),
+			end:             NewTimeOfDay(6, 0, 0),
+			weekdays:        []time.Weekday{time.Sunday},
+			location:        time.UTC,
+			now:             time.Date(2006, time.December, 4, 5, 59, 0, 0, time.UTC),
+			expectedInRange: true,
+		},
+		{
+			label:           "6:01AM Monday, crossing midnight",
+			start:           NewTimeOfDay(19, 0, 0),
+			end:             NewTimeOfDay(6, 0, 0),
+			weekdays:        []time.Weekday{time.Sunday},
+			location:        time.UTC,
+			now:             time.Date(2006, time.December, 4, 6, 1, 0, 0, time.UTC),
+			expectedInRange: false,
+		},
 	}
 
 	for _, tc := range testcases {