diff --git a/frontend/src/lib/lunchProtection.ts b/frontend/src/lib/lunchProtection.ts
index effd50d..30ca7b6 100644
--- a/frontend/src/lib/lunchProtection.ts
+++ b/frontend/src/lib/lunchProtection.ts
@@ -58,21 +58,20 @@ export function calculateMiddleWindow(
 }
 
 /**
- * Find the largest gap in the middle window after accounting for bookings
- * Returns the duration in minutes of the largest gap
+ * Find all gaps in the middle window after accounting for bookings
+ * Returns an array of gap durations in minutes, sorted descending
  */
-export function findLargestLunchGap(
+export function findAllLunchGaps(
 	middleWindowStart: number,
 	middleWindowEnd: number,
 	existingBookings: TimeSlot[],
 	proposedBooking?: TimeSlot
-): number {
+): number[] {
 	const allBookings: TimeSlot[] = [...existingBookings];
 	if (proposedBooking) {
 		allBookings.push(proposedBooking);
 	}
 
-	// Filter to only bookings that overlap with the middle window
 	const relevantBookings = allBookings
 		.filter((booking) => {
 			const bookingStart = timeToMinutes(booking.startTime);
@@ -86,30 +85,49 @@ export function findLargestLunchGap(
 		.sort((a, b) => a.startTime - b.startTime);
 
 	if (relevantBookings.length === 0) {
-		return middleWindowEnd - middleWindowStart;
+		return [middleWindowEnd - middleWindowStart];
 	}
 
-	let largestGap = 0;
+	const gaps: number[] = [];
 
 	const firstBookingStart = relevantBookings[0].startTime;
 	if (firstBookingStart > middleWindowStart) {
-		largestGap = Math.max(largestGap, firstBookingStart - middleWindowStart);
+		gaps.push(firstBookingStart - middleWindowStart);
 	}
 
 	for (let i = 0; i < relevantBookings.length - 1; i++) {
 		const gapStart = relevantBookings[i].endTime;
 		const gapEnd = relevantBookings[i + 1].startTime;
 		if (gapEnd > gapStart) {
-			largestGap = Math.max(largestGap, gapEnd - gapStart);
+			gaps.push(gapEnd - gapStart);
 		}
 	}
 
 	const lastBookingEnd = relevantBookings[relevantBookings.length - 1].endTime;
 	if (lastBookingEnd < middleWindowEnd) {
-		largestGap = Math.max(largestGap, middleWindowEnd - lastBookingEnd);
+		gaps.push(middleWindowEnd - lastBookingEnd);
 	}
 
-	return largestGap;
+	return gaps.sort((a, b) => b - a);
+}
+
+/**
+ * Find the largest gap in the middle window after accounting for bookings
+ * Returns the duration in minutes of the largest gap
+ */
+export function findLargestLunchGap(
+	middleWindowStart: number,
+	middleWindowEnd: number,
+	existingBookings: TimeSlot[],
+	proposedBooking?: TimeSlot
+): number {
+	const gaps = findAllLunchGaps(
+		middleWindowStart,
+		middleWindowEnd,
+		existingBookings,
+		proposedBooking
+	);
+	return gaps.length > 0 ? gaps[0] : 0;
 }
 
 export const LUNCH_MINIMUM_USER = 60;
@@ -141,10 +159,12 @@ export function checkLunchProtection(
 		endTime: proposedSlotEnd
 	};
 
-	const largestGap = findLargestLunchGap(windowStart, windowEnd, existingBookings, proposedBooking);
+	const gapWithout = findLargestLunchGap(windowStart, windowEnd, existingBookings);
+	const gapsWith = findAllLunchGaps(windowStart, windowEnd, existingBookings, proposedBooking);
+	const gapWith = gapsWith[0] ?? 0;
 
 	if (isAdmin) {
-		if (largestGap < LUNCH_MINIMUM_ADMIN) {
+		if (gapWith < LUNCH_MINIMUM_ADMIN && gapWith < gapWithout) {
 			return {
 				isBlocked: true,
 				showWarning: false,
@@ -152,18 +172,43 @@ export function checkLunchProtection(
 			};
 		}
 
-		if (largestGap < LUNCH_WARNING_THRESHOLD) {
-			const gapMinutes = Math.round(largestGap);
+		if (gapWith < LUNCH_WARNING_THRESHOLD && gapWith < gapWithout) {
+			const startH = parseInt(proposedSlotStart.split(':')[0], 10);
+			const startM = parseInt(proposedSlotStart.split(':')[1], 10);
+			const endH = parseInt(proposedSlotEnd.split(':')[0], 10);
+			const endM = parseInt(proposedSlotEnd.split(':')[1], 10);
+			const fmt = (h: number, m: number) => {
+				const p = h >= 12 ? 'PM' : 'AM';
+				return `${h % 12 || 12}:${String(m).padStart(2, '0')} ${p}`;
+			};
+
+			const viableGaps = gapsWith.filter((g) => g >= LUNCH_MINIMUM_ADMIN);
+			if (viableGaps.length >= 2 && gapsWith.every((g) => g >= LUNCH_MINIMUM_ADMIN)) {
+				const sorted = [...viableGaps].sort((a, b) => b - a);
+				if (sorted[0] === sorted[1]) {
+					return {
+						isBlocked: false,
+						showWarning: true,
+						warningMessage: `This booking (${fmt(startH, startM)}–${fmt(endH, endM)}) would split your suggested lunch break into two ${sorted[0]} minute blocks.`
+					};
+				}
+				return {
+					isBlocked: false,
+					showWarning: true,
+					warningMessage: `This booking (${fmt(startH, startM)}–${fmt(endH, endM)}) would split your suggested lunch break into ${sorted[0]} and ${sorted[1]} minute blocks.`
+				};
+			}
+
 			return {
 				isBlocked: false,
 				showWarning: true,
-				warningMessage: `Warning: This booking would reduce lunch break to ${gapMinutes} minutes.`
+				warningMessage: `This booking (${fmt(startH, startM)}–${fmt(endH, endM)}) would reduce lunch break to ${gapWith} minutes.`
 			};
 		}
 
 		return { isBlocked: false, showWarning: false };
 	} else {
-		if (largestGap < LUNCH_MINIMUM_USER) {
+		if (gapWith < LUNCH_MINIMUM_USER && gapWith < gapWithout) {
 			return {
 				isBlocked: true,
 				showWarning: false,