diff --git a/conformance/tests/gateway-observed-generation-bump.go b/conformance/tests/gateway-observed-generation-bump.go
new file mode 100644
index 0000000000..5dc9bf2b20
--- /dev/null
+++ b/conformance/tests/gateway-observed-generation-bump.go
@@ -0,0 +1,100 @@
+/*
+Copyright 2022 The Kubernetes 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.
+*/
+
+package tests
+
+import (
+	"context"
+	"testing"
+	"time"
+
+	"github.com/stretchr/testify/require"
+	"k8s.io/apimachinery/pkg/types"
+
+	"sigs.k8s.io/gateway-api/apis/v1beta1"
+	"sigs.k8s.io/gateway-api/conformance/utils/kubernetes"
+	"sigs.k8s.io/gateway-api/conformance/utils/suite"
+)
+
+func init() {
+	ConformanceTests = append(ConformanceTests, GatewayObservedGenerationBump)
+}
+
+var GatewayObservedGenerationBump = suite.ConformanceTest{
+	ShortName:   "GatewayObservedGenerationBump",
+	Description: "A Gateway in the gateway-conformance-infra namespace should update the observedGeneration in all of it's Status.Conditions after an update to the spec",
+	Manifests:   []string{"tests/gateway-observed-generation-bump.yaml"},
+	Test: func(t *testing.T, s *suite.ConformanceTestSuite) {
+
+		gwNN := types.NamespacedName{Name: "observed-generation-bump", Namespace: "gateway-conformance-infra"}
+
+		t.Run("observedGeneration should increment", func(t *testing.T) {
+			ctx, cancel := context.WithTimeout(context.Background(), 20*time.Second)
+			defer cancel()
+
+			namespaces := []string{"gateway-conformance-infra"}
+			kubernetes.NamespacesMustBeAccepted(t, s.Client, s.TimeoutConfig, namespaces)
+
+			existing := &v1beta1.Gateway{}
+			err := s.Client.Get(ctx, gwNN, existing)
+			require.NoErrorf(t, err, "error getting Gateway: %v", err)
+
+			// Sanity check
+			if kubernetes.ConditionsHaveLatestObservedGeneration(existing, existing.Status.Conditions) {
+				t.Fatal("Not all the condition's observedGeneration were updated")
+			}
+
+			all := v1beta1.NamespacesFromAll
+
+			// mutate the Gateway Spec
+			existing.Spec.Listeners = append(existing.Spec.Listeners, v1beta1.Listener{
+				Name:     "alternate",
+				Port:     80,
+				Protocol: v1beta1.HTTPProtocolType,
+				AllowedRoutes: &v1beta1.AllowedRoutes{
+					Namespaces: &v1beta1.RouteNamespaces{From: &all},
+				},
+			})
+
+			err = s.Client.Update(ctx, existing)
+			require.NoErrorf(t, err, "error updating the Gateway: %v", err)
+
+			// Ensure the generation and observedGeneration sync up
+			kubernetes.NamespacesMustBeAccepted(t, s.Client, s.TimeoutConfig, namespaces)
+
+			updated := &v1beta1.Gateway{}
+			err = s.Client.Get(ctx, gwNN, updated)
+			require.NoErrorf(t, err, "error getting Gateway: %v", err)
+
+			// Sanity check
+			if kubernetes.ConditionsHaveLatestObservedGeneration(updated, updated.Status.Conditions) {
+				t.Fatal("Not all the condition's observedGeneration were updated")
+			}
+
+			if existing.Generation == updated.Generation {
+				t.Errorf("expected generation to change because of spec change - remained at %v", updated.Generation)
+			}
+
+			for _, uc := range updated.Status.Conditions {
+				for _, ec := range existing.Status.Conditions {
+					if ec.Type == uc.Type && ec.ObservedGeneration == uc.ObservedGeneration {
+						t.Errorf("expected status condition %v observedGeneration to change - remained at %v", updated.Generation)
+					}
+				}
+			}
+		})
+	},
+}
diff --git a/conformance/tests/gateway-observed-generation-bump.yaml b/conformance/tests/gateway-observed-generation-bump.yaml
new file mode 100644
index 0000000000..31fe593d9f
--- /dev/null
+++ b/conformance/tests/gateway-observed-generation-bump.yaml
@@ -0,0 +1,14 @@
+apiVersion: gateway.networking.k8s.io/v1beta1
+kind: Gateway
+metadata:
+  name: gateway-observed-generation-bump
+  namespace: gateway-conformance-infra
+spec:
+  gatewayClassName: "{GATEWAY_CLASS_NAME}"
+  listeners:
+    - name: http
+      port: 80
+      protocol: HTTP
+      allowedRoutes:
+        namespaces:
+          from: All