diff --git a/internal/gatewayapi/status/error.go b/internal/gatewayapi/status/error.go
index 7e310da62b..57b712fb8e 100644
--- a/internal/gatewayapi/status/error.go
+++ b/internal/gatewayapi/status/error.go
@@ -225,7 +225,7 @@ func (m *MultiStatusError) Reason() gwapiv1.RouteConditionReason {
 		reasonList = append(reasonList, reason)
 	}
 	sort.Strings(reasonList)
-	return gwapiv1.RouteConditionReason(strings.Join(reasonList, ", "))
+	return gwapiv1.RouteConditionReason(strings.Join(reasonList, ","))
 }
 
 func (m *MultiStatusError) Type() gwapiv1.RouteConditionType {
diff --git a/internal/gatewayapi/testdata/grpcroute-with-conflicting-filters.out.yaml b/internal/gatewayapi/testdata/grpcroute-with-conflicting-filters.out.yaml
index 798bd83c26..6138ba86ed 100644
--- a/internal/gatewayapi/testdata/grpcroute-with-conflicting-filters.out.yaml
+++ b/internal/gatewayapi/testdata/grpcroute-with-conflicting-filters.out.yaml
@@ -80,7 +80,7 @@ grpcRoutes:
         message: |-
           Dropped Rule(s) [0]: Invalid filter ExtensionRef: unknown kind gateway.envoyproxy.io/HTTPRouteFilter.
           RequestMirror filter cannot be used when the rule also configures a DirectResponse filter.
-        reason: IncompatibleFilters, UnsupportedValue
+        reason: IncompatibleFilters,UnsupportedValue
         status: "True"
         type: PartiallyInvalid
       - lastTransitionTime: null
diff --git a/internal/gatewayapi/testdata/httproute-with-urlrewrite-hostname-filter.in.yaml b/internal/gatewayapi/testdata/httproute-with-urlrewrite-hostname-filter.in.yaml
index f39c951e5f..09b7115694 100644
--- a/internal/gatewayapi/testdata/httproute-with-urlrewrite-hostname-filter.in.yaml
+++ b/internal/gatewayapi/testdata/httproute-with-urlrewrite-hostname-filter.in.yaml
@@ -125,6 +125,42 @@ httpRoutes:
           path:
             type: ReplacePrefixMatch
             replacePrefixMatch: /rewrite
+- apiVersion: gateway.networking.k8s.io/v1
+  kind: HTTPRoute
+  metadata:
+    namespace: default
+    name: httproute-5
+  spec:
+    hostnames:
+    - gateway.envoyproxy.io
+    parentRefs:
+    - namespace: envoy-gateway
+      name: gateway-1
+      sectionName: http
+    rules:
+    - matches:
+      - path:
+          value: "/not-found-filter"
+      backendRefs:
+      - name: service-1
+        port: 8080
+        filters:
+        - type: ExtensionRef
+          extensionRef:
+            group: gateway.envoyproxy.io
+            kind: HTTPRouteFilter
+            name: not-found-filter
+      filters:
+      - type: URLRewrite
+        urlRewrite:
+          path:
+            type: ReplacePrefixMatch
+            replacePrefixMatch: /rewrite
+      - type: ExtensionRef
+        extensionRef:
+          group: gateway.envoyproxy.io
+          kind: HTTPRouteFilter
+          name: not-found-filter
 httpFilters:
 - apiVersion: gateway.envoyproxy.io/v1alpha1
   kind: HTTPRouteFilter
diff --git a/internal/gatewayapi/testdata/httproute-with-urlrewrite-hostname-filter.out.yaml b/internal/gatewayapi/testdata/httproute-with-urlrewrite-hostname-filter.out.yaml
index badf61f847..0dca8c386c 100644
--- a/internal/gatewayapi/testdata/httproute-with-urlrewrite-hostname-filter.out.yaml
+++ b/internal/gatewayapi/testdata/httproute-with-urlrewrite-hostname-filter.out.yaml
@@ -16,7 +16,7 @@ gateways:
       protocol: HTTP
   status:
     listeners:
-    - attachedRoutes: 4
+    - attachedRoutes: 5
       conditions:
       - lastTransitionTime: null
         message: Sending translated listener configuration to the data plane
@@ -222,6 +222,62 @@ httpRoutes:
         name: gateway-1
         namespace: envoy-gateway
         sectionName: http
+- apiVersion: gateway.networking.k8s.io/v1
+  kind: HTTPRoute
+  metadata:
+    name: httproute-5
+    namespace: default
+  spec:
+    hostnames:
+    - gateway.envoyproxy.io
+    parentRefs:
+    - name: gateway-1
+      namespace: envoy-gateway
+      sectionName: http
+    rules:
+    - backendRefs:
+      - filters:
+        - extensionRef:
+            group: gateway.envoyproxy.io
+            kind: HTTPRouteFilter
+            name: not-found-filter
+          type: ExtensionRef
+        name: service-1
+        port: 8080
+      filters:
+      - type: URLRewrite
+        urlRewrite:
+          path:
+            replacePrefixMatch: /rewrite
+            type: ReplacePrefixMatch
+      - extensionRef:
+          group: gateway.envoyproxy.io
+          kind: HTTPRouteFilter
+          name: not-found-filter
+        type: ExtensionRef
+      matches:
+      - path:
+          value: /not-found-filter
+  status:
+    parents:
+    - conditions:
+      - lastTransitionTime: null
+        message: Route is accepted
+        reason: Accepted
+        status: "True"
+        type: Accepted
+      - lastTransitionTime: null
+        message: |-
+          Unable to translate HTTPRouteFilter: default/not-found-filter.
+          Failed to process route rule 0 backendRef 0: Unable to translate HTTPRouteFilter: default/not-found-filter.
+        reason: InvalidBackendFilters,UnsupportedValue
+        status: "False"
+        type: ResolvedRefs
+      controllerName: gateway.envoyproxy.io/gatewayclass-controller
+      parentRef:
+        name: gateway-1
+        namespace: envoy-gateway
+        sectionName: http
 infraIR:
   envoy-gateway/gateway-1:
     proxy:
@@ -355,6 +411,23 @@ xdsIR:
           path:
             fullReplace: null
             prefixMatchReplace: /rewrite
+      - directResponse:
+          statusCode: 500
+        hostname: gateway.envoyproxy.io
+        isHTTP2: false
+        metadata:
+          kind: HTTPRoute
+          name: httproute-5
+          namespace: default
+        name: httproute/default/httproute-5/rule/0/match/0/gateway_envoyproxy_io
+        pathMatch:
+          distinct: false
+          name: ""
+          prefix: /not-found-filter
+        urlRewrite:
+          path:
+            fullReplace: null
+            prefixMatchReplace: /rewrite
       - destination:
           metadata:
             kind: HTTPRoute
diff --git a/release-notes/current.yaml b/release-notes/current.yaml
index a77ca0a894..871279210f 100644
--- a/release-notes/current.yaml
+++ b/release-notes/current.yaml
@@ -76,6 +76,7 @@ bug fixes: |
   Fixed gateway-helm RBAC in GatewayNamespace mode with explicit `watch.namespaces` list by adding controller-namespace secret read permissions to infra-manager.
   Fixed a control plane panic caused by concurrent Status mutation racing with the watchable Map coalesce goroutine.
   Fixed BackendTrafficPolicy rate limit `requests` values above uint32 max (4294967295) being silently truncated modulo 2^32 by the rate limit service and Envoy token bucket. The field now rejects such values at admission time with a clear schema validation error. See envoyproxy/ai-gateway#2012.
+  Fixed status conditions not being updated when a route is rejected due to multiple errors.
 
 # Enhancements that improve performance.
 performance improvements: |