diff --git a/source/gateway.go b/source/gateway.go
index 2a71352126..77203819b9 100644
--- a/source/gateway.go
+++ b/source/gateway.go
@@ -333,10 +333,11 @@ func (c *gatewayRouteResolver) resolve(rt gatewayRoute) (map[string]endpoint.Tar
 		}
 
 		// Confirm the Gateway has accepted the Route.
-		if !gwRouteIsAccepted(rps.Conditions) {
-			log.Debugf("Gateway %s/%s has not accepted %s %s/%s", namespace, ref.Name, c.src.rtKind, meta.Namespace, meta.Name)
+		if !gwRouteIsAccepted(rps.Conditions, meta) {
+			log.Debugf("Gateway %s/%s has not accepted the current generation %s %s/%s", namespace, ref.Name, c.src.rtKind, meta.Namespace, meta.Name)
 			continue
 		}
+
 		// Match the Route to all possible Listeners.
 		match := false
 		section := sectionVal(ref.SectionName, "")
@@ -494,10 +495,10 @@ func gwRouteHasParentRef(routeParentRefs []v1.ParentReference, ref v1.ParentRefe
 	return false
 }
 
-func gwRouteIsAccepted(conds []metav1.Condition) bool {
+func gwRouteIsAccepted(conds []metav1.Condition, meta *metav1.ObjectMeta) bool {
 	for _, c := range conds {
 		if v1.RouteConditionType(c.Type) == v1.RouteConditionAccepted {
-			return c.Status == metav1.ConditionTrue
+			return c.Status == metav1.ConditionTrue && c.ObservedGeneration == meta.Generation
 		}
 	}
 	return false
diff --git a/source/gateway_httproute_test.go b/source/gateway_httproute_test.go
index 19f009fb75..a7f9bbe90e 100644
--- a/source/gateway_httproute_test.go
+++ b/source/gateway_httproute_test.go
@@ -70,6 +70,36 @@ func gwRouteStatus(refs ...v1.ParentReference) v1.RouteStatus {
 	return v
 }
 
+func omWithGeneration(meta metav1.ObjectMeta, generation int64) metav1.ObjectMeta {
+	meta.Generation = generation
+	return meta
+}
+
+func rsWithGeneration(routeStatus v1.HTTPRouteStatus, generation ...int64) v1.HTTPRouteStatus {
+	for i, parent := range routeStatus.Parents {
+		if len(generation) <= i {
+			break
+		}
+
+		parent.Conditions[0].ObservedGeneration = generation[i]
+	}
+
+	return routeStatus
+}
+
+func rsWithoutAccepted(routeStatus v1.HTTPRouteStatus) v1.HTTPRouteStatus {
+	for _, parent := range routeStatus.Parents {
+		for j := range parent.Conditions {
+			cond := &parent.Conditions[j]
+			if cond.Type == string(v1.RouteConditionAccepted) {
+				cond.Type = "NotAccepted" // fake type to test for having no accepted condition
+			}
+		}
+	}
+
+	return routeStatus
+}
+
 func gwParentRef(namespace, name string, options ...gwParentRefOption) v1.ParentReference {
 	group := v1.Group("gateway.networking.k8s.io")
 	kind := v1.Kind("Gateway")
@@ -192,6 +222,81 @@ func TestGatewayHTTPRouteSourceEndpoints(t *testing.T) {
 				"level=debug msg=\"Gateway gateway-namespace/not-gateway-name does not match gateway-name route-namespace/test\"",
 			},
 		},
+		{
+			title: "GatewayNameOldGeneration",
+			config: Config{
+				GatewayName: "gateway-name",
+			},
+			namespaces: namespaces("gateway-namespace", "route-namespace"),
+			gateways: []*v1beta1.Gateway{
+				{
+					ObjectMeta: omWithGeneration(objectMeta("gateway-namespace", "gateway-name"), 2),
+					Spec: v1.GatewaySpec{
+						Listeners: []v1.Listener{{
+							Protocol:      v1.HTTPProtocolType,
+							AllowedRoutes: allowAllNamespaces,
+						}},
+					},
+					Status: gatewayStatus("1.2.3.4"),
+				},
+			},
+			routes: []*v1beta1.HTTPRoute{{
+				ObjectMeta: omWithGeneration(objectMeta("route-namespace", "old-test"), 5),
+				Spec: v1.HTTPRouteSpec{
+					Hostnames: hostnames("test.example.internal"),
+					CommonRouteSpec: v1.CommonRouteSpec{
+						ParentRefs: []v1.ParentReference{
+							gwParentRef("gateway-namespace", "gateway-name"),
+						},
+					},
+				},
+				Status: rsWithGeneration(httpRouteStatus( // The route was previously attached in a different generation
+					gwParentRef("gateway-namespace", "gateway-name"),
+					gwParentRef("gateway-namespace", "gateway-name"),
+				), 5, 4),
+			}},
+			endpoints: []*endpoint.Endpoint{
+				newTestEndpoint("test.example.internal", "A", "1.2.3.4"),
+			},
+			logExpectations: []string{
+				"level=debug msg=\"Gateway gateway-namespace/gateway-name has not accepted the current generation HTTPRoute route-namespace/old-test\"",
+			},
+		},
+		{
+			title: "GatewayNameNoneAccepted",
+			config: Config{
+				GatewayName: "gateway-name",
+			},
+			namespaces: namespaces("gateway-namespace", "route-namespace"),
+			gateways: []*v1beta1.Gateway{
+				{
+					ObjectMeta: omWithGeneration(objectMeta("gateway-namespace", "gateway-name"), 2),
+					Spec: v1.GatewaySpec{
+						Listeners: []v1.Listener{{
+							Protocol:      v1.HTTPProtocolType,
+							AllowedRoutes: allowAllNamespaces,
+						}},
+					},
+					Status: gatewayStatus("1.2.3.4"),
+				},
+			},
+			routes: []*v1beta1.HTTPRoute{{
+				ObjectMeta: omWithGeneration(objectMeta("route-namespace", "old-test"), 5),
+				Spec: v1.HTTPRouteSpec{
+					Hostnames: hostnames("test.example.internal"),
+					CommonRouteSpec: v1.CommonRouteSpec{
+						ParentRefs: []v1.ParentReference{
+							gwParentRef("gateway-namespace", "gateway-name"),
+						},
+					},
+				},
+				Status: rsWithoutAccepted(httpRouteStatus(gwParentRef("gateway-namespace", "gateway-name"))),
+			}},
+			endpoints: []*endpoint.Endpoint{},
+			logExpectations: []string{
+				"level=debug msg=\"Gateway gateway-namespace/gateway-name has not accepted the current generation HTTPRoute route-namespace/old-test\"",
+			},
+		},
 		{
 			title: "GatewayNamespace",
 			config: Config{