diff --git a/internal/controller/assets/create_ltpa_config.sh b/internal/controller/assets/create_ltpa_config.sh
index b80b7d41..c32e868f 100644
--- a/internal/controller/assets/create_ltpa_config.sh
+++ b/internal/controller/assets/create_ltpa_config.sh
@@ -63,10 +63,10 @@ LAST_ROTATION=$(curl --cacert ${CACERT} --header "Content-Type: application/json
 PASSWORD=$(curl --cacert ${CACERT} --header "Content-Type: application/json" --header "Authorization: Bearer ${TOKEN}" -X GET ${APISERVER}/api/v1/namespaces/${NAMESPACE}/secrets/${LTPA_SECRET_NAME} | grep -o '"password": "[^"]*' | grep -o '[^"]*$' | base64 -d);
 
 if [ "$ENCRYPTION_KEY_SHARING_ENABLED" == "true" ] && [ $NOT_FOUND_COUNT -eq 0 ]; then
-    PASSWORD_KEY_LAST_ROTATION=$(curl --cacert ${CACERT} --header "Content-Type: application/json" --header "Authorization: Bearer ${TOKEN}" -X GET ${APISERVER}/api/v1/namespaces/${NAMESPACE}/secrets/${PASSWORD_KEY_SECRET_NAME} | grep -o '"lastRotation": "[^"]*' | grep -o '[^"]*$' | base64 -d);
-    PASSWORD_KEY=$(curl --cacert ${CACERT} --header "Content-Type: application/json" --header "Authorization: Bearer ${TOKEN}" -X GET ${APISERVER}/api/v1/namespaces/${NAMESPACE}/secrets/${PASSWORD_KEY_SECRET_NAME} | grep -o '"passwordEncryptionKey": "[^"]*' | grep -o '[^"]*$' | base64 -d);
-    ENCODED_PASSWORD=$(securityUtility encode --encoding=${ENCODING_TYPE} --key=${PASSWORD_KEY} ${PASSWORD});
-    LTPA_ENCODED_PASSWORD="{\"apiVersion\": \"v1\", \"stringData\": {\"lastRotation\": \"$LAST_ROTATION\", \"password\": \"$ENCODED_PASSWORD\"}, \"kind\": \"Secret\",\"metadata\": {\"name\": \"$LTPA_CONFIG_SECRET_NAME\", \"passwordKeyLastRotation\": \"$PASSWORD_KEY_LAST_ROTATION\", \"namespace\": \"$NAMESPACE\",\"labels\": {\"app.kubernetes.io/name\": \"${LTPA_CONFIG_BASE_NAME}\", \"app.kubernetes.io/instance\": \"${LTPA_CONFIG_SECRET_NAME}\", \"$LTPA_LABEL_KEY\": \"$LTPA_LABEL_VALUE\"}},\"type\": \"Opaque\"}";
+    ENCRYPTION_KEY_LAST_ROTATION=$(curl --cacert ${CACERT} --header "Content-Type: application/json" --header "Authorization: Bearer ${TOKEN}" -X GET ${APISERVER}/api/v1/namespaces/${NAMESPACE}/secrets/${PASSWORD_KEY_SECRET_NAME} | grep -o '"lastRotation": "[^"]*' | grep -o '[^"]*$' | base64 -d);
+    ENCRYPTION_KEY=$(curl --cacert ${CACERT} --header "Content-Type: application/json" --header "Authorization: Bearer ${TOKEN}" -X GET ${APISERVER}/api/v1/namespaces/${NAMESPACE}/secrets/${PASSWORD_KEY_SECRET_NAME} | grep -o '"passwordEncryptionKey": "[^"]*' | grep -o '[^"]*$' | base64 -d);
+    ENCODED_PASSWORD=$(securityUtility encode --encoding=${ENCODING_TYPE} --key=${ENCRYPTION_KEY} ${PASSWORD});
+    LTPA_ENCODED_PASSWORD="{\"apiVersion\": \"v1\", \"stringData\": {\"encryptionKeyLastRotation\": \"$ENCRYPTION_KEY_LAST_ROTATION\", \"lastRotation\": \"$LAST_ROTATION\", \"password\": \"$ENCODED_PASSWORD\"}, \"kind\": \"Secret\",\"metadata\": {\"name\": \"$LTPA_CONFIG_SECRET_NAME\", \"passwordKeyLastRotation\": \"$PASSWORD_KEY_LAST_ROTATION\", \"namespace\": \"$NAMESPACE\",\"labels\": {\"app.kubernetes.io/name\": \"${LTPA_CONFIG_BASE_NAME}\", \"app.kubernetes.io/instance\": \"${LTPA_CONFIG_SECRET_NAME}\", \"$LTPA_LABEL_KEY\": \"$LTPA_LABEL_VALUE\"}},\"type\": \"Opaque\"}";
 else
     SECRET_NAME="${LTPA_SECRET_NAME}-password"
     ENCODED_PASSWORD=$(securityUtility encode --encoding=${ENCODING_TYPE} ${PASSWORD});
diff --git a/internal/controller/ltpa_keys_sharing.go b/internal/controller/ltpa_keys_sharing.go
index 7524bb05..baf37d42 100644
--- a/internal/controller/ltpa_keys_sharing.go
+++ b/internal/controller/ltpa_keys_sharing.go
@@ -609,7 +609,8 @@ func (r *ReconcileOpenLiberty) generateLTPAConfig(instance *olv1.OpenLibertyAppl
 
 	ltpaConfigSecret := &corev1.Secret{}
 	ltpaConfigSecretRootName := OperatorShortName + "-managed-ltpa"
-	if r.isUsingPasswordEncryptionKeySharing(instance, passwordEncryptionMetadata) {
+	isPasswordEncryptionKeySharing := r.isUsingPasswordEncryptionKeySharing(instance, passwordEncryptionMetadata)
+	if isPasswordEncryptionKeySharing {
 		ltpaConfigSecretRootName += "-keyed-password"
 		ltpaConfigSecret.Name = ltpaConfigSecretRootName + ltpaConfigMetadata.Name
 	} else {
@@ -801,6 +802,33 @@ func (r *ReconcileOpenLiberty) generateLTPAConfig(instance *olv1.OpenLibertyAppl
 		return err
 	}
 
+	// if using encryption key, check if the key has been rotated and requires a regeneration of the LTPA keyed password
+	if isPasswordEncryptionKeySharing {
+		internalEncryptionKeySecret, err := r.hasInternalEncryptionKeySecret(instance, passwordEncryptionMetadata)
+		if err != nil {
+			return err
+		}
+		lastRotation, found := internalEncryptionKeySecret.Data["lastRotation"]
+		if !found {
+			// lastRotation field is not present so the Secret was not initialized correctly
+			err := r.DeleteResource(internalEncryptionKeySecret)
+			if err != nil {
+				return err
+			}
+			return fmt.Errorf("the internal encryption key secret does not contain field 'lastRotation'")
+		}
+
+		if encryptionKeyLastRotation, found := ltpaConfigSecret.Data["encryptionKeyLastRotation"]; found {
+			if string(encryptionKeyLastRotation) != string(lastRotation) {
+				err := r.DeleteResource(ltpaConfigSecret)
+				if err != nil {
+					return err
+				}
+				return fmt.Errorf("the encryption key has been modified; waiting for a new LTPA password to be generated")
+			}
+		}
+	}
+
 	// Create/update the Secret to hold the server.xml that will import the LTPA keys into the Liberty server
 	// This server.xml will be mounted in /config/configDropins/overrides/ltpaKeysMount.xml
 	serverXMLMountSecretErr := r.GetClient().Get(context.TODO(), types.NamespacedName{Name: ltpaXMLMountSecret.Name, Namespace: ltpaXMLMountSecret.Namespace}, ltpaXMLMountSecret)