killbill-aplcache

diff --git a/entitlement/src/main/java/org/killbill/billing/entitlement/api/DefaultEntitlement.java b/entitlement/src/main/java/org/killbill/billing/entitlement/api/DefaultEntitlement.java
index 72fb0c2..f1ec38c 100644
--- a/entitlement/src/main/java/org/killbill/billing/entitlement/api/DefaultEntitlement.java
+++ b/entitlement/src/main/java/org/killbill/billing/entitlement/api/DefaultEntitlement.java
@@ -298,6 +298,10 @@ public class DefaultEntitlement extends EntityBase implements Entitlement {
         // Get the latest state from disk
         refresh(callContext);
 
+        if (entitlementEffectiveDate != null && entitlementEffectiveDate.compareTo(getEffectiveStartDate()) < 0) {
+            throw new EntitlementApiException(ErrorCode.SUB_INVALID_REQUESTED_DATE, entitlementEffectiveDate, getEffectiveStartDate());
+        }
+
         final LocalDate billingEffectiveDate = overrideBillingEffectiveDate ? entitlementEffectiveDate : null;
         final EntitlementContext pluginContext = new DefaultEntitlementContext(OperationType.CANCEL_SUBSCRIPTION,
                                                                                getAccountId(),