diff --git a/changelog/v1.19.0-beta3/fix-flakey-TestConfigureNotAttachedHttpListenerOptions.yaml b/changelog/v1.19.0-beta3/fix-flakey-TestConfigureNotAttachedHttpListenerOptions.yaml
new file mode 100644
index 00000000000..6b358150fb1
--- /dev/null
+++ b/changelog/v1.19.0-beta3/fix-flakey-TestConfigureNotAttachedHttpListenerOptions.yaml
@@ -0,0 +1,4 @@
+changelog:
+- type: NON_USER_FACING
+  issueLink: https://github.com/solo-io/solo-projects/issues/6617
+  description: Fix flakey TestConfigureNotAttachedHttpListenerOptions caused by the gateway-proxy pod being deployed after the test begins leading to a timeout.
diff --git a/test/gomega/matchers/pod.go b/test/gomega/matchers/pod.go
index 12f95dfeb29..bf15cac6d9f 100644
--- a/test/gomega/matchers/pod.go
+++ b/test/gomega/matchers/pod.go
@@ -16,6 +16,9 @@ type ExpectedPod struct {
 	// Status is the pod phase status (e.g. Running, Pending, Succeeded, Failed). Optional.
 	Status corev1.PodPhase
 
+	// Ready indicates that the Pod is able to serve requests. Optional.
+	Ready bool
+
 	// TODO(npolshak): Add more fields to match on as needed
 }
 
@@ -41,28 +44,47 @@ func (pm *podMatcher) Match(actual interface{}) (bool, error) {
 			}
 		}
 		if !foundContainer {
-			log.Printf("expected pod to have container '%s', but it was not found", pm.expectedPod.ContainerName)
+			log.Printf("expected pod %s to have container '%s', but it was not found", pod.Name, pm.expectedPod.ContainerName)
 			return false, nil
 		}
 	}
 
 	if pm.expectedPod.Status != "" {
 		if pod.Status.Phase != pm.expectedPod.Status {
-			log.Printf("expected pod to have status %s, but it was %s", pm.expectedPod.Status, pod.Status.Phase)
+			log.Printf("expected pod %s to have status %s, but it was %s", pod.Name, pm.expectedPod.Status, pod.Status.Phase)
 			return false, nil
 		}
 	}
 
+	if pm.expectedPod.Ready {
+		for _, condition := range pod.Status.Conditions {
+			if condition.Type == corev1.PodReady {
+				ready := condition.Status == corev1.ConditionTrue
+				if !ready {
+					log.Printf("expected pod %s to have condition ready, but it was not ready", pod.Name)
+				}
+				return ready, nil
+			}
+		}
+		log.Printf("expected pod %s to have condition ready, but it was not found", pod.Name)
+		return false, nil
+	}
+
 	return true, nil
 }
 
 func (pm *podMatcher) FailureMessage(actual interface{}) string {
 	var errorMsg string
+	pod, ok := actual.(corev1.Pod)
+	if !ok {
+		return fmt.Sprintf("expected a pod, got %T", actual)
+	}
+
 	if pm.expectedPod.ContainerName != "" {
-		errorMsg += fmt.Sprintf("Expected pod to have container '%s', but it was not found", pm.expectedPod.ContainerName)
+		errorMsg += fmt.Sprintf("Expected pod %s to have container '%s', but it was not found", pod.Name, pm.expectedPod.ContainerName)
 	}
 	if pm.expectedPod.Status != "" {
-		errorMsg += fmt.Sprintf("Expected pod to have status '%s', but it was not found", pm.expectedPod.Status)
+		errorMsg += fmt.Sprintf("Expected pod %s to have status '%s', but it was not found", pod.Name, pm.expectedPod.Status)
 	}
 	return errorMsg
 }
@@ -76,10 +98,10 @@ func (pm *podMatcher) NegatedFailureMessage(actual interface{}) string {
 		for _, container := range pod.Spec.Containers {
 			containers += container.Name + ", "
 		}
-		errorMsg += fmt.Sprintf("Expected pod to have container '%s', but it found %s", pm.expectedPod.ContainerName, containers)
+		errorMsg += fmt.Sprintf("Expected pod %s to have container '%s', but it found %s", pod.Name, pm.expectedPod.ContainerName, containers)
 	}
 	if pm.expectedPod.Status != "" {
-		errorMsg += fmt.Sprintf("Expected pod to have status '%s', but it found %s", pm.expectedPod.Status, pod.Status.Phase)
+		errorMsg += fmt.Sprintf("Expected pod %s to have status '%s', but it found %s", pod.Name, pm.expectedPod.Status, pod.Status.Phase)
 	}
 	return errorMsg
 }
diff --git a/test/kubernetes/e2e/features/http_listener_options/http_lis_opt_suite.go b/test/kubernetes/e2e/features/http_listener_options/http_lis_opt_suite.go
index e0f5177ae90..2e08b17927d 100644
--- a/test/kubernetes/e2e/features/http_listener_options/http_lis_opt_suite.go
+++ b/test/kubernetes/e2e/features/http_listener_options/http_lis_opt_suite.go
@@ -45,6 +45,9 @@ func (s *testingSuite) SetupSuite() {
 	s.testInstallation.Assertions.EventuallyPodsRunning(s.ctx, nginxPod.ObjectMeta.GetNamespace(), metav1.ListOptions{
 		LabelSelector: "app.kubernetes.io/name=nginx",
 	})
+	s.testInstallation.Assertions.EventuallyPodsRunning(s.ctx, testdefaults.CurlPod.GetNamespace(), metav1.ListOptions{
+		LabelSelector: "app=curl",
+	})
 
 	// include gateway manifests for the tests, so we recreate it for each test run
 	s.manifests = map[string][]string{
@@ -88,6 +91,10 @@ func (s *testingSuite) AfterTest(suiteName, testName string) {
 		output, err := s.testInstallation.Actions.Kubectl().DeleteFileWithOutput(s.ctx, manifest)
 		s.testInstallation.Assertions.ExpectObjectDeleted(manifest, err, output)
 	}
+	s.testInstallation.Assertions.EventuallyObjectsNotExist(s.ctx, proxyService, proxyDeployment)
+	s.testInstallation.Assertions.EventuallyPodsNotExist(s.ctx, proxyDeployment.ObjectMeta.GetNamespace(), metav1.ListOptions{
+		LabelSelector: "app.kubernetes.io/name=gloo-proxy-gw",
+	})
 }
 
 func (s *testingSuite) TestConfigureHttpListenerOptions() {
diff --git a/test/kubernetes/testutils/assertions/pods.go b/test/kubernetes/testutils/assertions/pods.go
index a39f8f99ff6..e578a0a1615 100644
--- a/test/kubernetes/testutils/assertions/pods.go
+++ b/test/kubernetes/testutils/assertions/pods.go
@@ -13,14 +13,14 @@ import (
 	metav1 "k8s.io/apimachinery/pkg/apis/meta/v1"
 )
 
-// EventuallyPodsRunning asserts that the pod(s) are in the ready state
+// EventuallyPodsRunning asserts that the pod(s) are running and ready.
 func (p *Provider) EventuallyPodsRunning(
 	ctx context.Context,
 	podNamespace string,
 	listOpt metav1.ListOptions,
 	timeout ...time.Duration,
 ) {
-	p.EventuallyPodsMatches(ctx, podNamespace, listOpt, matchers.PodMatches(matchers.ExpectedPod{Status: corev1.PodRunning}), timeout...)
+	p.EventuallyPodsMatches(ctx, podNamespace, listOpt, matchers.PodMatches(matchers.ExpectedPod{Status: corev1.PodRunning, Ready: true}), timeout...)
 }
 
 // EventuallyPodsMatches asserts that the pod(s) in the given namespace matches the provided matcher
@@ -45,3 +45,22 @@ func (p *Provider) EventuallyPodsMatches(
 		WithPolling(pollingInterval).
 		Should(gomega.Succeed(), fmt.Sprintf("Failed to match pod in namespace %s", podNamespace))
 }
+
+// EventuallyPodsNotExist asserts that the pod(s) are no longer present
+func (p *Provider) EventuallyPodsNotExist(
+	ctx context.Context,
+	podNamespace string,
+	listOpt metav1.ListOptions,
+	timeout ...time.Duration,
+) {
+	currentTimeout, pollingInterval := helper.GetTimeouts(timeout...)
+
+	p.Gomega.Eventually(func(g gomega.Gomega) {
+		pods, err := p.clusterContext.Clientset.CoreV1().Pods(podNamespace).List(ctx, listOpt)
+		g.Expect(err).NotTo(gomega.HaveOccurred(), "Failed to list pods")
+		g.Expect(pods.Items).To(gomega.BeEmpty(), "Pods found")
+	}).
+		WithTimeout(currentTimeout).
+		WithPolling(pollingInterval).
+		Should(gomega.Succeed(), fmt.Sprintf("Failed to match pod in namespace %s", podNamespace))
+}