diff --git a/config/maintenance/maintenance.go b/config/maintenance/maintenance.go
index 967443db..72ab5f56 100644
--- a/config/maintenance/maintenance.go
+++ b/config/maintenance/maintenance.go
@@ -110,12 +110,13 @@ func (c *Config) IsUnderMaintenance() bool {
 	if c.TimezoneLocation != nil {
 		now = now.In(c.TimezoneLocation)
 	}
-	var dayWhereMaintenancePeriodWouldStart time.Time
-	if now.Hour() >= int(c.durationToStartFromMidnight.Hours()) {
-		dayWhereMaintenancePeriodWouldStart = now.Truncate(24 * time.Hour)
-	} else {
-		dayWhereMaintenancePeriodWouldStart = now.Add(-c.Duration).Truncate(24 * time.Hour)
+	adjustedDate := now.Day()
+	if now.Hour() < int(c.durationToStartFromMidnight.Hours()) {
+		// if time in maintenance window is later than now, treat it as yesterday
+		adjustedDate--
 	}
+	// Set to midnight prior to adding duration
+	dayWhereMaintenancePeriodWouldStart := time.Date(now.Year(), now.Month(), adjustedDate, 0, 0, 0, 0, now.Location())
 	hasMaintenanceEveryDay := len(c.Every) == 0
 	hasMaintenancePeriodScheduledToStartOnThatWeekday := c.hasDay(dayWhereMaintenancePeriodWouldStart.Weekday().String())
 	if !hasMaintenanceEveryDay && !hasMaintenancePeriodScheduledToStartOnThatWeekday {
diff --git a/config/maintenance/maintenance_test.go b/config/maintenance/maintenance_test.go
index edbdad37..f8ba5cab 100644
--- a/config/maintenance/maintenance_test.go
+++ b/config/maintenance/maintenance_test.go
@@ -264,6 +264,15 @@ func TestConfig_IsUnderMaintenance(t *testing.T) {
 			},
 			expected: true,
 		},
+		{
+			name: "under-maintenance-perth-timezone-starting-now-for-2h",
+			cfg: &Config{
+				Start:    fmt.Sprintf("%02d:00", inTimezone(now, "Australia/Perth", t).Hour()),
+				Duration: 2 * time.Hour,
+				Timezone: "Australia/Perth",
+			},
+			expected: true,
+		},
 		{
 			name: "under-maintenance-utc-timezone-starting-now-for-2h",
 			cfg: &Config{
@@ -340,3 +349,12 @@ func normalizeHour(hour int) int {
 	}
 	return hour
 }
+
+func inTimezone(passedTime time.Time, timezone string, t *testing.T) time.Time {
+	timezoneLocation, err := time.LoadLocation(timezone)
+
+	if err != nil {
+		t.Fatalf("timezone %s did not load", timezone)
+	}
+	return passedTime.In(timezoneLocation)
+}