diff --git a/core/src/main/java/de/bstly/we/businesslogic/PermissionManager.java b/core/src/main/java/de/bstly/we/businesslogic/PermissionManager.java
index bc8ec51..cd8fc92 100755
--- a/core/src/main/java/de/bstly/we/businesslogic/PermissionManager.java
+++ b/core/src/main/java/de/bstly/we/businesslogic/PermissionManager.java
@@ -416,7 +416,11 @@ public class PermissionManager implements UserDataProvider {
 				List<Permission> existingPermissions = get(target, name);
 
 				for (Permission existingPermission : existingPermissions) {
-					if (existingPermission.getExpires().isBefore(permissionsExpires)) {
+					if (existingPermission.getExpires().isBefore(permissionsExpires)
+							|| permissionMapping.isLifetimeRound() && InstantHelper
+									.truncate(existingPermission.getExpires(), permissionMapping.getLifetimeUnit())
+									.isBefore(InstantHelper.truncate(permissionsExpires,
+											permissionMapping.getLifetimeUnit()))) {
 						if (starts != null) {
 							if (existingPermission.getStarts() == null || existingPermission.getStarts().isAfter(starts)
 									|| existingPermission.getExpires().isAfter(starts)) {