diff --git a/test/e2e/httpproxy/001_required_field_validation_test.go b/test/e2e/httpproxy/001_required_field_validation_test.go
new file mode 100644
index 00000000000..18dd63873ee
--- /dev/null
+++ b/test/e2e/httpproxy/001_required_field_validation_test.go
@@ -0,0 +1,150 @@
+// Copyright Project Contour Authors
+// Licensed under the Apache License, Version 2.0 (the "License");
+// you may not use this file except in compliance with the License.
+// You may obtain a copy of the License at
+//
+//     http://www.apache.org/licenses/LICENSE-2.0
+//
+// Unless required by applicable law or agreed to in writing, software
+// distributed under the License is distributed on an "AS IS" BASIS,
+// WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+// See the License for the specific language governing permissions and
+// limitations under the License.
+
+// +build e2e
+
+package httpproxy
+
+import (
+	"context"
+
+	contourv1 "github.com/projectcontour/contour/apis/projectcontour/v1"
+	"github.com/projectcontour/contour/test/e2e"
+	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/require"
+	metav1 "k8s.io/apimachinery/pkg/apis/meta/v1"
+	"k8s.io/apimachinery/pkg/apis/meta/v1/unstructured"
+)
+
+func testRequiredFieldValidation(fx *e2e.Framework) {
+	t := fx.T()
+	ns := "001-required-field-validation"
+
+	fx.CreateNamespace(ns)
+	defer fx.DeleteNamespace(ns)
+
+	// This HTTPProxy is expressed as an Unstructured because the JSON
+	// tags for the relevant field do not include "omitempty", so when
+	// a typed Go struct is serialized to JSON the field *is* included
+	// and therefore does not fail validation.
+	missingConditionHeaderName := &unstructured.Unstructured{
+		Object: map[string]interface{}{
+			"apiVersion": "projectcontour.io/v1",
+			"kind":       "HTTPProxy",
+			"metadata": map[string]interface{}{
+				"name":      "missing-condition-header-name",
+				"namespace": ns,
+			},
+			"spec": map[string]interface{}{
+				"routes": []map[string]interface{}{
+					{
+						"conditions": []map[string]interface{}{
+							{
+								"header": map[string]interface{}{
+									"present": true,
+								},
+							},
+						},
+						"services": []map[string]interface{}{
+							{
+								"name": "foo",
+								"port": 80,
+							},
+						},
+					},
+				},
+			},
+		},
+	}
+
+	err := fx.Client.Create(context.TODO(), missingConditionHeaderName)
+	require.Error(t, err)
+	assert.Contains(t, err.Error(), "spec.routes.conditions.header.name: Required value")
+
+	// This HTTPProxy is expressed as an Unstructured because the JSON
+	// tags for the relevant field do not include "omitempty", so when
+	// a typed Go struct is serialized to JSON the field *is* included
+	// and therefore does not fail validation.
+	missingVirtualHostName := &unstructured.Unstructured{
+		Object: map[string]interface{}{
+			"apiVersion": "projectcontour.io/v1",
+			"kind":       "HTTPProxy",
+			"metadata": map[string]interface{}{
+				"name":      "missing-virtualhost-name",
+				"namespace": ns,
+			},
+			"spec": map[string]interface{}{
+				"virtualhost": map[string]interface{}{
+					"tls": map[string]interface{}{
+						"passthrough": true,
+					},
+				},
+			},
+		},
+	}
+
+	err = fx.Client.Create(context.TODO(), missingVirtualHostName)
+	require.Error(t, err)
+	assert.Contains(t, err.Error(), "spec.virtualhost.fqdn: Required value")
+
+	// This HTTPProxy is expressed as an Unstructured because the JSON
+	// tags for the relevant field do not include "omitempty", so when
+	// a typed Go struct is serialized to JSON the field *is* included
+	// and therefore does not fail validation.
+	missingIncludesName := &unstructured.Unstructured{
+		Object: map[string]interface{}{
+			"apiVersion": "projectcontour.io/v1",
+			"kind":       "HTTPProxy",
+			"metadata": map[string]interface{}{
+				"name":      "missing-includes-name",
+				"namespace": ns,
+			},
+			"spec": map[string]interface{}{
+				"includes": []map[string]interface{}{
+					{
+						"namespace": "foo",
+					},
+				},
+			},
+		},
+	}
+
+	err = fx.Client.Create(context.TODO(), missingIncludesName)
+	require.Error(t, err)
+	assert.Contains(t, err.Error(), "spec.includes.name: Required value")
+
+	servicePortRange := &contourv1.HTTPProxy{
+		ObjectMeta: metav1.ObjectMeta{
+			Namespace: ns,
+			Name:      "service-port-range",
+		},
+		Spec: contourv1.HTTPProxySpec{
+			VirtualHost: &contourv1.VirtualHost{
+				Fqdn: "ports.projectcontour.io",
+			},
+			Routes: []contourv1.Route{
+				{
+					Services: []contourv1.Service{
+						{
+							Name: "any-service-name",
+							Port: 80000,
+						},
+					},
+				},
+			},
+		},
+	}
+	err = fx.Client.Create(context.TODO(), servicePortRange)
+	require.Error(t, err)
+	assert.Contains(t, err.Error(), "spec.routes.services.port: Invalid value")
+}
diff --git a/test/e2e/httpproxy/011_retry_policy_validation_test.go b/test/e2e/httpproxy/011_retry_policy_validation_test.go
new file mode 100644
index 00000000000..eab6a3885f0
--- /dev/null
+++ b/test/e2e/httpproxy/011_retry_policy_validation_test.go
@@ -0,0 +1,61 @@
+// Copyright Project Contour Authors
+// Licensed under the Apache License, Version 2.0 (the "License");
+// you may not use this file except in compliance with the License.
+// You may obtain a copy of the License at
+//
+//     http://www.apache.org/licenses/LICENSE-2.0
+//
+// Unless required by applicable law or agreed to in writing, software
+// distributed under the License is distributed on an "AS IS" BASIS,
+// WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+// See the License for the specific language governing permissions and
+// limitations under the License.
+
+// +build e2e
+
+package httpproxy
+
+import (
+	"context"
+
+	contourv1 "github.com/projectcontour/contour/apis/projectcontour/v1"
+	"github.com/projectcontour/contour/test/e2e"
+	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/require"
+	metav1 "k8s.io/apimachinery/pkg/apis/meta/v1"
+)
+
+func testRetryPolicyValidation(fx *e2e.Framework) {
+	t := fx.T()
+	ns := "011-retry-policy-validation"
+
+	fx.CreateNamespace(ns)
+	defer fx.DeleteNamespace(ns)
+
+	p := &contourv1.HTTPProxy{
+		ObjectMeta: metav1.ObjectMeta{
+			Namespace: ns,
+			Name:      "invalid-retry-on-condition",
+		},
+		Spec: contourv1.HTTPProxySpec{
+			Routes: []contourv1.Route{
+				{
+					Services: []contourv1.Service{
+						{
+							Name: "foo",
+							Port: 80,
+						},
+					},
+					RetryPolicy: &contourv1.RetryPolicy{
+						RetryOn: []contourv1.RetryOn{
+							"foobar",
+						},
+					},
+				},
+			},
+		},
+	}
+	err := fx.Client.Create(context.TODO(), p)
+	require.Error(t, err)
+	assert.Contains(t, err.Error(), "spec.routes.retryPolicy.retryOn: Unsupported value")
+}
diff --git a/test/e2e/httpproxy/httpproxy_test.go b/test/e2e/httpproxy/httpproxy_test.go
index 013dbeb0644..edb41e0b6c7 100644
--- a/test/e2e/httpproxy/httpproxy_test.go
+++ b/test/e2e/httpproxy/httpproxy_test.go
@@ -34,6 +34,9 @@ var _ = Describe("HTTPProxy", func() {
 		f = e2e.NewFramework(GinkgoT())
 	})
 
+	It("001-required-field-validation", func() {
+		testRequiredFieldValidation(f)
+	})
 	It("002-header-condition-match", func() {
 		testHeaderConditionMatch(f)
 	})
@@ -58,6 +61,9 @@ var _ = Describe("HTTPProxy", func() {
 	It("010-include-prefix-condition", func() {
 		testIncludePrefixCondition(f)
 	})
+	It("011-retry-policy-validation", func() {
+		testRetryPolicyValidation(f)
+	})
 	It("012-https-fallback-certificate", func() {
 		testHTTPSFallbackCertificate(f)
 	})