diff --git a/vmware_nsx/plugins/nsx_p/plugin.py b/vmware_nsx/plugins/nsx_p/plugin.py
index b1abf9db59..0ff0c60ed7 100644
--- a/vmware_nsx/plugins/nsx_p/plugin.py
+++ b/vmware_nsx/plugins/nsx_p/plugin.py
@@ -1698,7 +1698,11 @@ class NsxPolicyPlugin(nsx_plugin_common.NsxPluginV3Base):
                 cidr1 = netaddr.IPNetwork(binding1.ip_address)
                 cidr2 = netaddr.IPNetwork(binding2.ip_address)
                 if cidr1 != cidr2 and cidr1 in cidr2:
-                    address_bindings.remove(binding1)
+                    try:
+                        address_bindings.remove(binding1)
+                    except ValueError:
+                        # Item was already removed
+                        pass
         return address_bindings
 
     def _get_network_nsx_id(self, context, network_id):
diff --git a/vmware_nsx/plugins/nsx_v3/plugin.py b/vmware_nsx/plugins/nsx_v3/plugin.py
index 57e4f5cc00..2b6f5a25aa 100644
--- a/vmware_nsx/plugins/nsx_v3/plugin.py
+++ b/vmware_nsx/plugins/nsx_v3/plugin.py
@@ -1205,7 +1205,11 @@ class NsxV3Plugin(nsx_plugin_common.NsxPluginV3Base,
                 cidr1 = netaddr.IPNetwork(binding1.ip_address)
                 cidr2 = netaddr.IPNetwork(binding2.ip_address)
                 if cidr1 != cidr2 and cidr1 in cidr2:
-                    address_bindings.remove(binding1)
+                    try:
+                        address_bindings.remove(binding1)
+                    except ValueError:
+                        # item already removed
+                        pass
 
         return address_bindings
 
diff --git a/vmware_nsx/tests/unit/nsx_p/test_plugin.py b/vmware_nsx/tests/unit/nsx_p/test_plugin.py
index 8a403655ea..b4e60033fa 100644
--- a/vmware_nsx/tests/unit/nsx_p/test_plugin.py
+++ b/vmware_nsx/tests/unit/nsx_p/test_plugin.py
@@ -1334,6 +1334,48 @@ class NsxPTestPorts(common_v3.NsxV3TestPorts,
                     set([fixed_ip, '1.2.3.0/24']),
                     addresses)
 
+    def test_update_port_allowed_pair_cidr(self):
+        with self.subnet() as subnet:
+            post_data = {
+                'port': {
+                    'network_id': subnet['subnet']['network_id'],
+                    'tenant_id': subnet['subnet']['tenant_id'],
+                    'allowed_address_pairs': [
+                        {'ip_address': '10.4.0.32',
+                         'mac_address': '00:00:5e:00:01:fa'},
+                        {'ip_address': '10.40.1.125',
+                         'mac_address': 'fa:16:3e:ef:b1:be'}],
+                    'device_owner': 'compute:meh',
+                    'fixed_ips': [{'subnet_id':
+                                    subnet['subnet']['id']}]}}
+            post_req = self.new_create_request('ports', post_data)
+            res = post_req.get_response(self.api)
+            self.assertEqual(201, res.status_int)
+            port = self.deserialize('json', res)
+            fixed_ip = (
+                port['port']['fixed_ips'][0]['ip_address'])
+            with mock.patch.object(
+                self.plugin.nsxpolicy.segment_port,
+                'create_or_overwrite') as mock_port:
+                put_data = {
+                    'port': {
+                        'allowed_address_pairs': [
+                            {'ip_address': '10.4.0.0/24'}
+                        ]
+                    }
+                }
+                put_req = self.new_update_request(
+                    'ports', put_data, port['port']['id'])
+                put_res = put_req.get_response(self.api)
+                self.assertEqual(200, put_res.status_int)
+                self.assertEqual(1, len(mock_port.mock_calls))
+                _n, _a, kwargs = mock_port.mock_calls[0]
+                actual_bindings = kwargs['address_bindings']
+                addresses = set([b.ip_address for b in actual_bindings])
+                self.assertEqual(
+                    set([fixed_ip, '10.4.0.0/24']),
+                    addresses)
+
 
 class NsxPTestSubnets(common_v3.NsxV3TestSubnets,
                       NsxPPluginTestCaseMixin):