diff --git a/admin/api/password.go b/admin/api/password.go
index 2c26cd9d..a626ee22 100644
--- a/admin/api/password.go
+++ b/admin/api/password.go
@@ -215,6 +215,12 @@ func genDexConfig() ([]byte, error) {
 		} else {
 			// Also generate team associations
 			for _, team := range teams {
+				if _, err := os.Stat(path.Join(TeamsDir, fmt.Sprintf("team%02d", team.Id))); err == nil {
+					if err = os.Remove(path.Join(TeamsDir, fmt.Sprintf("team%02d", team.Id))); err != nil {
+						log.Println("Unable to remove existing association symlink:", err.Error())
+						return nil, fmt.Errorf("Unable to remove existing association symlink: %s", err.Error())
+					}
+				}
 				if err := os.Symlink(fmt.Sprintf("%d", team.Id), path.Join(TeamsDir, fmt.Sprintf("team%02d", team.Id))); err != nil {
 					log.Println("Unable to create association symlink:", err.Error())
 					return nil, fmt.Errorf("Unable to create association symlink: %s", err.Error())