diff --git a/g2p_programs/models/cycle_membership.py b/g2p_programs/models/cycle_membership.py
index 683980bc..f4e90cc1 100644
--- a/g2p_programs/models/cycle_membership.py
+++ b/g2p_programs/models/cycle_membership.py
@@ -91,12 +91,17 @@ def unlink(self):
             )
 
         for record in draft_records:
-            beneficiary = record.cycle_id.entitlement_ids.filtered(
+            entitlement = record.cycle_id.entitlement_ids.filtered(
                 lambda x: x.partner_id.id == record.partner_id.id
             )
-            if record.cycle_id.state == "approved" or beneficiary and beneficiary.state == "approved":
-                raise ValidationError(
-                    _("Beneficiaries can only be deleted when both the cycle and entitlement are unapproved.")
-                )
+            if entitlement:
+                if entitlement.state == "approved":
+                    raise ValidationError(
+                        _(
+                            "Beneficiaries can only be deleted when both the cycle and"
+                            "entitlement are unapproved."
+                        )
+                    )
+                entitlement.unlink()
 
         return super().unlink()
diff --git a/g2p_programs/models/entitlement.py b/g2p_programs/models/entitlement.py
index 9887c18d..935bcaff 100644
--- a/g2p_programs/models/entitlement.py
+++ b/g2p_programs/models/entitlement.py
@@ -96,6 +96,14 @@ def _generate_code(self):
         ),
     ]
 
+    @api.constrains("valid_from", "valid_until")
+    def _check_valid_dates(self):
+        for record in self:
+            if record.valid_until and record.valid_from and record.valid_until < record.valid_from:
+                raise ValidationError(
+                    _('The "Valid Until" date cannot be earlier than the "Valid From" date.')
+                )
+
     def fields_view_get(self, view_id=None, view_type="list", toolbar=False, submenu=False):
         res = super(G2PEntitlement, self).fields_view_get(
             view_id=view_id, view_type=view_type, toolbar=toolbar, submenu=submenu