diff --git a/AdvancedCore/src/main/java/com/bencodez/advancedcore/api/time/TimeChecker.java b/AdvancedCore/src/main/java/com/bencodez/advancedcore/api/time/TimeChecker.java
index 90ea353242..135acfe8a4 100644
--- a/AdvancedCore/src/main/java/com/bencodez/advancedcore/api/time/TimeChecker.java
+++ b/AdvancedCore/src/main/java/com/bencodez/advancedcore/api/time/TimeChecker.java
@@ -242,13 +242,15 @@ public boolean hasDayChanged(boolean set) {
 
 	public boolean hasMonthChanged(boolean set) {
 		String prevMonth = plugin.getServerDataFile().getPrevMonth();
-		String month = getTime().getMonth().toString();
+		LocalDateTime current = getTime();
+		String month = current.getMonth().toString();
 		if (prevMonth.equals(month)) return false;
 		if (set) plugin.getServerDataFile().setPrevMonth(month);
-		if (!plugin.getOptions().isTimeChangeFailSafeBypass() && getTime().getDayOfMonth() > 3) {
+		LocalDateTime graceEnd = current.withDayOfMonth(1).toLocalDate().atStartOfDay().plusHours(12);
+		if (!plugin.getOptions().isTimeChangeFailSafeBypass() && current.isAfter(graceEnd)) {
 			plugin.getLogger().warning(
-					"Detected a month change, but current day is not near end of a month, ignoring month change, "
-							+ getTime().getDayOfMonth());
+					"Detected a month change outside the first 12 hours of the month, ignoring month change: "
+							+ current);
 			plugin.getServerDataFile().setPrevMonth(month);
 			return false;
 		}
diff --git a/AdvancedCore/src/main/java/com/bencodez/advancedcore/bungeeapi/time/BungeeTimeChecker.java b/AdvancedCore/src/main/java/com/bencodez/advancedcore/bungeeapi/time/BungeeTimeChecker.java
index 892c1d5166..ee47c85be6 100644
--- a/AdvancedCore/src/main/java/com/bencodez/advancedcore/bungeeapi/time/BungeeTimeChecker.java
+++ b/AdvancedCore/src/main/java/com/bencodez/advancedcore/bungeeapi/time/BungeeTimeChecker.java
@@ -102,16 +102,18 @@ public boolean hasDayChanged(boolean set) {
 
 	public boolean hasMonthChanged(boolean set) {
 		String prevMonth = getPrevMonth();
-		String month = getTime().getMonth().toString();
+		LocalDateTime current = getTime();
+		String month = current.getMonth().toString();
 		if (prevMonth.equals(month)) {
 			return false;
 		}
 		if (set) {
 			setPrevMonth(month);
 		}
-		if (!timeChangeFailSafeBypass && getTime().getDayOfMonth() > 3) {
-			warning("Detected a month change, but current day is not near end of a month, ignoring month change, "
-					+ getTime().getDayOfMonth());
+		LocalDateTime graceEnd = current.withDayOfMonth(1).toLocalDate().atStartOfDay().plusHours(12);
+		if (!timeChangeFailSafeBypass && current.isAfter(graceEnd)) {
+			warning("Detected a month change outside the first 12 hours of the month, ignoring month change: "
+					+ current);
 			setPrevMonth(month);
 			return false;
 		}
diff --git a/AdvancedCore/src/test/java/com/bencodez/advancedcore/tests/time/BungeeTimeCheckerTest.java b/AdvancedCore/src/test/java/com/bencodez/advancedcore/tests/time/BungeeTimeCheckerTest.java
index 55561f0262..47e6d27a33 100644
--- a/AdvancedCore/src/test/java/com/bencodez/advancedcore/tests/time/BungeeTimeCheckerTest.java
+++ b/AdvancedCore/src/test/java/com/bencodez/advancedcore/tests/time/BungeeTimeCheckerTest.java
@@ -367,6 +367,10 @@ public void warning(String text) {
 
 		assertTrue(result);
 		verify(timeChecker).setPrevMonth("NOVEMBER");
+
+		Mockito.doReturn(LocalDateTime.of(2023, 11, 1, 12, 0, 1)).when(timeChecker).getTime();
+		assertFalse(timeChecker.hasMonthChanged(false));
+		verify(timeChecker, Mockito.times(2)).setPrevMonth("NOVEMBER");
 	}
 
 	@Test
diff --git a/AdvancedCore/src/test/java/com/bencodez/advancedcore/tests/time/TimeCheckerTest.java b/AdvancedCore/src/test/java/com/bencodez/advancedcore/tests/time/TimeCheckerTest.java
index c6ccc1b6b1..90570c4fbe 100644
--- a/AdvancedCore/src/test/java/com/bencodez/advancedcore/tests/time/TimeCheckerTest.java
+++ b/AdvancedCore/src/test/java/com/bencodez/advancedcore/tests/time/TimeCheckerTest.java
@@ -149,6 +149,22 @@ public void testDayWeekMonthChanges() {
 		}
 	}
 
+	@Test
+	public void monthChangeFailSafeRejectsStaleChangeAfterTwelveHours() {
+		when(serverDataFile.getPrevMonth()).thenReturn("DECEMBER");
+		when(options.isTimeChangeFailSafeBypass()).thenReturn(false);
+		when(plugin.getLogger()).thenReturn(Logger.getLogger("TimeCheckerTest"));
+
+		TimeChecker timeChecker = Mockito.spy(new TimeChecker(plugin));
+
+		Mockito.doReturn(LocalDateTime.of(2025, 1, 1, 12, 0)).when(timeChecker).getTime();
+		assertTrue(timeChecker.hasMonthChanged(false));
+
+		Mockito.doReturn(LocalDateTime.of(2025, 1, 1, 12, 0, 1)).when(timeChecker).getTime();
+		assertFalse(timeChecker.hasMonthChanged(false));
+		verify(serverDataFile).setPrevMonth("JANUARY");
+	}
+
 	@Test
 	public void detectedTransitionAdvancesMarkerOnlyAfterSuccessfulDispatch() {
 		TimeChangeTransitionState transition = transitionState();