diff --git a/CHANGELOG-EE b/CHANGELOG-EE
index d5fabbb0cb9877b3d256c0760bfbdac59d089a9b..645119369c89fe37b5bb66d593e2a13ce5b5d1f5 100644
--- a/CHANGELOG-EE
+++ b/CHANGELOG-EE
@@ -3,6 +3,9 @@ Please view this file on the master branch, on stable branches it's out of date.
 v 8.10.0 (unreleased)
   - Rename Git Hooks to Push Rules
 
+v 8.9.5
+  - Prevent stale data in LDAP group sync last owner check.
+
 v 8.9.4
   - Improve how File Lock feature works with nested items. !497
 
diff --git a/lib/gitlab/ldap/group_sync.rb b/lib/gitlab/ldap/group_sync.rb
index 88886759755d53d01cb8bb300ee4ebb86d9ba455..86a445f5ebedc707e7ff951b0ed8c72025cb33b6 100644
--- a/lib/gitlab/ldap/group_sync.rb
+++ b/lib/gitlab/ldap/group_sync.rb
@@ -304,6 +304,11 @@ def update_existing_group_membership(group, access_levels)
             next
           end
 
+          # Since we're removing users in this loop, `group.reload`
+          # before checking `last_owner?` to prevent stale owner information.
+          # Without a reload, this check would return a false negative.
+          group.reload
+
           # Check and update the access level. If `desired_access` is `nil`
           # we need to delete the user from the group.
           if desired_access.present?