diff --git a/CHANGELOG.md b/CHANGELOG.md
index 3a085d7..4ac12ea 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -11,6 +11,9 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
 - Improve add/remove admin emails
 - Added Valid From to Invitation Flow
 
+### Fixed
+- Correct calculation of membership expiration for enrollment request of an already member
+
 ## [0.21.1]
 
 ### Fixed
diff --git a/src/main/java/org/rciam/plugins/groups/jpa/repositories/UserGroupMembershipExtensionRepository.java b/src/main/java/org/rciam/plugins/groups/jpa/repositories/UserGroupMembershipExtensionRepository.java
index 28b08e5..e1e4548 100644
--- a/src/main/java/org/rciam/plugins/groups/jpa/repositories/UserGroupMembershipExtensionRepository.java
+++ b/src/main/java/org/rciam/plugins/groups/jpa/repositories/UserGroupMembershipExtensionRepository.java
@@ -430,9 +430,11 @@ public void createOrUpdate(GroupEnrollmentRequestEntity enrollmentEntity, Keyclo
         if (isNotMember) {
             entity.setValidFrom(configuration.getValidFrom() == null || !configuration.getValidFrom().isAfter(LocalDate.now()) ? LocalDate.now() : configuration.getValidFrom());
         }
-        if (configuration.getMembershipExpirationDays() != null) {
+        if (configuration.getMembershipExpirationDays() != null && entity.getValidFrom().isAfter(LocalDate.now())) {
             entity.setMembershipExpiresAt(entity.getValidFrom().plusDays(configuration.getMembershipExpirationDays()));
-        } else {
+        } else if (configuration.getMembershipExpirationDays() != null) {
+            entity.setMembershipExpiresAt(LocalDate.now().plusDays(configuration.getMembershipExpirationDays()));
+        }else {
             entity.setMembershipExpiresAt(null);
         }
         entity.setGroup(configuration.getGroup());