diff --git a/config/maintenance/maintenance.go b/config/maintenance/maintenance.go
index d34f6a99..c5c12660 100644
--- a/config/maintenance/maintenance.go
+++ b/config/maintenance/maintenance.go
@@ -95,10 +95,15 @@ func (c Config) IsUnderMaintenance() bool {
 		return false
 	}
 	now := time.Now().UTC()
-	dayWhereMaintenancePeriodWouldStart := now.Add(-c.Duration).Truncate(24 * time.Hour)
+	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)
+	}
 	hasMaintenanceEveryDay := len(c.Every) == 0
-	hasMaintenancePeriodScheduledForThatWeekday := c.hasDay(dayWhereMaintenancePeriodWouldStart.Weekday().String())
-	if !hasMaintenanceEveryDay && !hasMaintenancePeriodScheduledForThatWeekday {
+	hasMaintenancePeriodScheduledToStartOnThatWeekday := c.hasDay(dayWhereMaintenancePeriodWouldStart.Weekday().String())
+	if !hasMaintenanceEveryDay && !hasMaintenancePeriodScheduledToStartOnThatWeekday {
 		// The day when the maintenance period would start is not scheduled
 		// to have any maintenance, so we can just return false.
 		return false
diff --git a/config/maintenance/maintenance_test.go b/config/maintenance/maintenance_test.go
index d90aabc9..b8cabfd1 100644
--- a/config/maintenance/maintenance_test.go
+++ b/config/maintenance/maintenance_test.go
@@ -153,7 +153,7 @@ func TestConfig_IsUnderMaintenance(t *testing.T) {
 			expected: true,
 		},
 		{
-			name: "under-maintenance",
+			name: "under-maintenance-starting-now-for-2h",
 			cfg: &Config{
 				Start:    fmt.Sprintf("%02d:00", now.Hour()),
 				Duration: 2 * time.Hour,
@@ -161,9 +161,33 @@ func TestConfig_IsUnderMaintenance(t *testing.T) {
 			expected: true,
 		},
 		{
-			name: "not-under-maintenance",
+			name: "under-maintenance-starting-now-for-8h",
 			cfg: &Config{
-				Start:    fmt.Sprintf("%02d:00", now.Add(-5*time.Hour).Hour()),
+				Start:    fmt.Sprintf("%02d:00", now.Hour()),
+				Duration: 8 * time.Hour,
+			},
+			expected: true,
+		},
+		{
+			name: "under-maintenance-starting-4h-ago-for-8h",
+			cfg: &Config{
+				Start:    fmt.Sprintf("%02d:00", now.Hour()-4),
+				Duration: 8 * time.Hour,
+			},
+			expected: true,
+		},
+		{
+			name: "under-maintenance-starting-4h-ago-for-3h",
+			cfg: &Config{
+				Start:    fmt.Sprintf("%02d:00", now.Hour()-4),
+				Duration: 3 * time.Hour,
+			},
+			expected: false,
+		},
+		{
+			name: "under-maintenance-starting-5h-ago-for-1h",
+			cfg: &Config{
+				Start:    fmt.Sprintf("%02d:00", now.Hour()-5),
 				Duration: time.Hour,
 			},
 			expected: false,