diff --git a/hack/make-rules/test-cmd.sh b/hack/make-rules/test-cmd.sh
index dab33477e7..1af9ae739c 100755
--- a/hack/make-rules/test-cmd.sh
+++ b/hack/make-rules/test-cmd.sh
@@ -2249,6 +2249,13 @@ __EOF__
   kubectl get rs nginx-618515232 -o yaml | grep "deployment.kubernetes.io/revision-history: 1,3"
   # Check that trying to watch the status of a superseded revision returns an error
   ! kubectl rollout status deployment/nginx --revision=3
+  cat hack/testdata/deployment-revision1.yaml | $SED "s/name: nginx$/name: nginx2/" | kubectl create -f - "${kube_flags[@]}"
+  # Newest deployment should be marked as overlapping
+  kubectl get deployment nginx2 -o yaml "${kube_flags[@]}" | grep "deployment.kubernetes.io/error-selector-overlapping-with"
+  # Oldest deployment should not be marked as overlapping
+  ! kubectl get deployment nginx -o yaml "${kube_flags[@]}" | grep "deployment.kubernetes.io/error-selector-overlapping-with"
+  # Deletion of both deployments should not be blocked
+   kubectl delete deployment nginx2 "${kube_flags[@]}"
   # Clean up
   kubectl delete deployment nginx "${kube_flags[@]}"
 
diff --git a/test/e2e/deployment.go b/test/e2e/deployment.go
index 82c6307470..02e2756fec 100644
--- a/test/e2e/deployment.go
+++ b/test/e2e/deployment.go
@@ -1255,11 +1255,11 @@ func testOverlappingDeployment(f *framework.Framework) {
 	Expect(err).NotTo(HaveOccurred(), "Failed creating the second deployment")
 
 	// Wait for overlapping annotation updated to both deployments
-	By("Waiting for both deployments to have overlapping annotations")
-	err = framework.WaitForOverlappingAnnotationMatch(c, ns, deploy.Name, deployOverlapping.Name)
-	Expect(err).NotTo(HaveOccurred(), "Failed to update the first deployment's overlapping annotation")
+	By("Waiting for the overlapping deployment to have overlapping annotation")
 	err = framework.WaitForOverlappingAnnotationMatch(c, ns, deployOverlapping.Name, deploy.Name)
 	Expect(err).NotTo(HaveOccurred(), "Failed to update the second deployment's overlapping annotation")
+	err = framework.WaitForOverlappingAnnotationMatch(c, ns, deploy.Name, "")
+	Expect(err).NotTo(HaveOccurred(), "The deployment that holds the oldest selector shouldn't have the overlapping annotation")
 
 	// Only the first deployment is synced
 	By("Checking only the first overlapping deployment is synced")
@@ -1311,11 +1311,11 @@ func testOverlappingDeployment(f *framework.Framework) {
 	Expect(err).NotTo(HaveOccurred())
 
 	// Wait for overlapping annotation updated to both deployments
-	By("Waiting for both deployments to have overlapping annotations")
-	err = framework.WaitForOverlappingAnnotationMatch(c, ns, deployOverlapping.Name, deployLater.Name)
-	Expect(err).NotTo(HaveOccurred(), "Failed to update the second deployment's overlapping annotation")
+	By("Waiting for the third deployment to have the overlapping annotation")
 	err = framework.WaitForOverlappingAnnotationMatch(c, ns, deployLater.Name, deployOverlapping.Name)
 	Expect(err).NotTo(HaveOccurred(), "Failed to update the third deployment's overlapping annotation")
+	err = framework.WaitForOverlappingAnnotationMatch(c, ns, deployOverlapping.Name, "")
+	Expect(err).NotTo(HaveOccurred(), "The deployment that holds the oldest selector shouldn't have the overlapping annotation")
 
 	// The second deployment shouldn't be synced
 	By("Checking the second deployment is not synced")