diff --git a/test/conformance/kuttl/ttl/past-timestamp/01-pod.yaml b/test/conformance/kuttl/ttl/past-timestamp/01-pod.yaml
index 52ffd92005..5486b71486 100644
--- a/test/conformance/kuttl/ttl/past-timestamp/01-pod.yaml
+++ b/test/conformance/kuttl/ttl/past-timestamp/01-pod.yaml
@@ -1,6 +1,4 @@
 apiVersion: kuttl.dev/v1beta1
 kind: TestStep
 apply:
-- pod.yaml
-assert:
-- pod-assert.yaml
\ No newline at end of file
+- pod.yaml
\ No newline at end of file
diff --git a/test/conformance/kuttl/ttl/past-timestamp/02-check.yaml b/test/conformance/kuttl/ttl/past-timestamp/02-check.yaml
new file mode 100644
index 0000000000..9c67825294
--- /dev/null
+++ b/test/conformance/kuttl/ttl/past-timestamp/02-check.yaml
@@ -0,0 +1,6 @@
+apiVersion: kuttl.dev/v1beta1
+kind: TestStep
+commands:
+- command: sleep 5
+error:
+- pod-assert.yaml
\ No newline at end of file
diff --git a/test/conformance/kuttl/ttl/past-timestamp/03-pod.yaml b/test/conformance/kuttl/ttl/past-timestamp/03-pod.yaml
new file mode 100644
index 0000000000..d785e1bad3
--- /dev/null
+++ b/test/conformance/kuttl/ttl/past-timestamp/03-pod.yaml
@@ -0,0 +1,6 @@
+apiVersion: kuttl.dev/v1beta1
+kind: TestStep
+apply:
+- pod-2.yaml
+assert:
+- pod-assert-2.yaml
\ No newline at end of file
diff --git a/test/conformance/kuttl/ttl/past-timestamp/02-wait.yaml b/test/conformance/kuttl/ttl/past-timestamp/04-patch.yaml
similarity index 60%
rename from test/conformance/kuttl/ttl/past-timestamp/02-wait.yaml
rename to test/conformance/kuttl/ttl/past-timestamp/04-patch.yaml
index 5b8bfb4701..b407e8ffaf 100644
--- a/test/conformance/kuttl/ttl/past-timestamp/02-wait.yaml
+++ b/test/conformance/kuttl/ttl/past-timestamp/04-patch.yaml
@@ -1,4 +1,4 @@
 apiVersion: kuttl.dev/v1beta1
 kind: TestStep
-commands:
-  - command: sleep 5
\ No newline at end of file
+apply:
+- past-timestamp.yaml
\ No newline at end of file
diff --git a/test/conformance/kuttl/ttl/past-timestamp/03-check.yaml b/test/conformance/kuttl/ttl/past-timestamp/05-check.yaml
similarity index 73%
rename from test/conformance/kuttl/ttl/past-timestamp/03-check.yaml
rename to test/conformance/kuttl/ttl/past-timestamp/05-check.yaml
index 024ee4f1b4..04fd99e7de 100644
--- a/test/conformance/kuttl/ttl/past-timestamp/03-check.yaml
+++ b/test/conformance/kuttl/ttl/past-timestamp/05-check.yaml
@@ -1,4 +1,4 @@
 apiVersion: kuttl.dev/v1beta1
 kind: TestStep
 error:
-- pod-assert.yaml
\ No newline at end of file
+- pod-assert-2.yaml
\ No newline at end of file
diff --git a/test/conformance/kuttl/ttl/past-timestamp/README.md b/test/conformance/kuttl/ttl/past-timestamp/README.md
index 85d30bac98..c0d0060141 100644
--- a/test/conformance/kuttl/ttl/past-timestamp/README.md
+++ b/test/conformance/kuttl/ttl/past-timestamp/README.md
@@ -6,4 +6,8 @@ This test cleans up pods instanteaously without any delay as the value of the la
 
 The pod `test-pod` is cleaned up instantaneously.
 
+The pod `test-pod-2` is cleaned up instantaneously when the label is updated to `cleanup.kyverno.io/ttl: 2023-07-19T120000Z` the timestamp is mentioned in past.
+
 ## Reference Issue(s)
+
+- [8242](https://github.com/kyverno/kyverno/issues/8242): `test-pod` might never be created, so the assert could fail.
diff --git a/test/conformance/kuttl/ttl/past-timestamp/past-timestamp.yaml b/test/conformance/kuttl/ttl/past-timestamp/past-timestamp.yaml
new file mode 100644
index 0000000000..7aca725c6d
--- /dev/null
+++ b/test/conformance/kuttl/ttl/past-timestamp/past-timestamp.yaml
@@ -0,0 +1,6 @@
+apiVersion: v1
+kind: Pod
+metadata:
+  name: test-pod-2
+  labels:
+    cleanup.kyverno.io/ttl: 2023-07-19T120000Z
\ No newline at end of file
diff --git a/test/conformance/kuttl/ttl/past-timestamp/pod-2.yaml b/test/conformance/kuttl/ttl/past-timestamp/pod-2.yaml
new file mode 100644
index 0000000000..9f96a38a24
--- /dev/null
+++ b/test/conformance/kuttl/ttl/past-timestamp/pod-2.yaml
@@ -0,0 +1,8 @@
+apiVersion: v1
+kind: Pod
+metadata:
+  name: test-pod-2
+spec:
+  containers:
+  - image: nginx:latest
+    name: nginx
diff --git a/test/conformance/kuttl/ttl/past-timestamp/pod-assert-2.yaml b/test/conformance/kuttl/ttl/past-timestamp/pod-assert-2.yaml
new file mode 100644
index 0000000000..cb80212cdf
--- /dev/null
+++ b/test/conformance/kuttl/ttl/past-timestamp/pod-assert-2.yaml
@@ -0,0 +1,4 @@
+apiVersion: v1
+kind: Pod
+metadata:
+  name: test-pod-2
\ No newline at end of file