diff --git a/pkg/timewindow/timewindow.go b/pkg/timewindow/timewindow.go
index 6ac1a0e..13e24d8 100644
--- a/pkg/timewindow/timewindow.go
+++ b/pkg/timewindow/timewindow.go
@@ -47,6 +47,19 @@ func (tw *TimeWindow) Contains(t time.Time) bool {
 	start := time.Date(loctime.Year(), loctime.Month(), loctime.Day(), tw.startTime.Hour(), tw.startTime.Minute(), tw.startTime.Second(), 0, tw.location)
 	end := time.Date(loctime.Year(), loctime.Month(), loctime.Day(), tw.endTime.Hour(), tw.endTime.Minute(), tw.endTime.Second(), 1e9-1, tw.location)
 
+	// Time Wrap validation
+	// First we check for start and end time, if start is after end time
+	// Next we need to validate if we want to wrap to the day before or to the day after
+	// For that we check the loctime value to see if it is before end time, we wrap with the day before
+	// Otherwise we wrap to the next day.
+	if tw.startTime.After(tw.endTime) {
+		if loctime.Before(end) {
+			start = start.Add(-24 * time.Hour)
+		} else {
+			end = end.Add(24 * time.Hour)
+		}
+	}
+
 	return (loctime.After(start) || loctime.Equal(start)) && (loctime.Before(end) || loctime.Equal(end))
 }
 
diff --git a/pkg/timewindow/timewindow_test.go b/pkg/timewindow/timewindow_test.go
index a629a45..ba1ffe3 100644
--- a/pkg/timewindow/timewindow_test.go
+++ b/pkg/timewindow/timewindow_test.go
@@ -20,12 +20,12 @@ func TestTimeWindows(t *testing.T) {
 		cases []testcase
 	}{
 		{"mon,tue,wed,thu,fri", "9am", "5pm", "America/Los_Angeles", []testcase{
-			{"2019/04/04 00:49 PDT", false},
-			{"2019/04/05 08:59 PDT", false},
-			{"2019/04/05 9:01 PDT", true},
 			{"2019/03/31 10:00 PDT", false},
+			{"2019/04/04 00:49 PDT", false},
 			{"2019/04/04 12:00 PDT", true},
 			{"2019/04/04 11:59 UTC", false},
+			{"2019/04/05 08:59 PDT", false},
+			{"2019/04/05 9:01 PDT", true},
 		}},
 		{"mon,we,fri", "10:01", "11:30am", "America/Los_Angeles", []testcase{
 			{"2019/04/05 10:30 PDT", true},
@@ -40,6 +40,43 @@ func TestTimeWindows(t *testing.T) {
 			{"2019/04/18 00:00 UTC", true},
 			{"2019/04/18 23:59 UTC", true},
 		}},
+		{"mon,tue,wed,thu,fri", "9pm", "5am", "America/Los_Angeles", []testcase{
+			{"2019/03/30 04:00 PDT", false},
+			{"2019/03/31 10:00 PDT", false},
+			{"2019/03/31 22:00 PDT", false},
+			{"2019/04/04 00:49 PDT", true},
+			{"2019/04/04 12:00 PDT", false},
+			{"2019/04/04 22:49 PDT", true},
+			{"2019/04/05 00:49 PDT", true},
+			{"2019/04/05 08:59 PDT", false},
+			{"2019/04/05 9:01 PDT", false},
+		}},
+		{"mon,tue,wed,thu,fri", "11:59pm", "00:01am", "America/Los_Angeles", []testcase{
+			{"2019/04/04 23:58 PDT", false},
+			{"2019/04/04 23:59 PDT", true},
+			{"2019/04/05 00:00 PDT", true},
+			{"2019/04/05 00:01 PDT", true},
+			{"2019/04/05 00:02 PDT", false},
+		}},
+		{"mon,tue,wed,fri", "11:59pm", "00:01am", "America/Los_Angeles", []testcase{
+			{"2019/04/04 23:58 PDT", false},
+			{"2019/04/04 23:59 PDT", false}, // Even that this falls in the between the hours Thursday is not included so should not run
+			{"2019/04/05 00:00 PDT", true},
+			{"2019/04/05 00:02 PDT", false},
+		}},
+		{"mon,tue,wed,thu", "11:59pm", "00:01am", "America/Los_Angeles", []testcase{
+			{"2019/04/04 23:58 PDT", false},
+			{"2019/04/04 23:59 PDT", true},
+			{"2019/04/05 00:00 PDT", false}, // Even that this falls in the between the hours Friday is not included so should not run
+			{"2019/04/05 00:02 PDT", false},
+		}},
+		{"mon,tue,wed,thu,fri", "11:59pm", "00:01am", "UTC", []testcase{
+			{"2019/04/04 23:58 UTC", false},
+			{"2019/04/04 23:59 UTC", true},
+			{"2019/04/05 00:00 UTC", true},
+			{"2019/04/05 00:01 UTC", true},
+			{"2019/04/05 00:02 UTC", false},
+		}},
 	}
 
 	for i, tst := range tests {