diff --git a/src/main/kotlin/com/android/trisolarisserver/controller/BookingFlow.kt b/src/main/kotlin/com/android/trisolarisserver/controller/BookingFlow.kt
index 6ff9b9e..5d5b765 100644
--- a/src/main/kotlin/com/android/trisolarisserver/controller/BookingFlow.kt
+++ b/src/main/kotlin/com/android/trisolarisserver/controller/BookingFlow.kt
@@ -80,7 +80,8 @@ class BookingFlow(
         }
 
         val now = nowForProperty(property.timezone)
-        val shouldCheckIn = !expectedCheckInAt.isAfter(now.plusMinutes(10))
+        val shouldCheckIn = expectedCheckInAt.isBefore(now) &&
+            !expectedCheckInAt.isBefore(now.minusMinutes(10))
         val phone = request.guestPhoneE164?.trim()?.takeIf { it.isNotBlank() }
         val guest = resolveGuestForBooking(propertyId, property, actor, now, phone)
         val hasGuestCounts = request.maleCount != null || request.femaleCount != null || request.childCount != null