diff --git a/test/conformance/kuttl/ttl/delete-twice/01-pod.yaml b/test/conformance/kuttl/ttl/delete-twice/01-pod.yaml
new file mode 100644
index 0000000000..52ffd92005
--- /dev/null
+++ b/test/conformance/kuttl/ttl/delete-twice/01-pod.yaml
@@ -0,0 +1,6 @@
+apiVersion: kuttl.dev/v1beta1
+kind: TestStep
+apply:
+- pod.yaml
+assert:
+- pod-assert.yaml
\ No newline at end of file
diff --git a/test/conformance/kuttl/ttl/delete-twice/02-check.yaml b/test/conformance/kuttl/ttl/delete-twice/02-check.yaml
new file mode 100644
index 0000000000..024ee4f1b4
--- /dev/null
+++ b/test/conformance/kuttl/ttl/delete-twice/02-check.yaml
@@ -0,0 +1,4 @@
+apiVersion: kuttl.dev/v1beta1
+kind: TestStep
+error:
+- pod-assert.yaml
\ No newline at end of file
diff --git a/test/conformance/kuttl/ttl/delete-twice/03-pod.yaml b/test/conformance/kuttl/ttl/delete-twice/03-pod.yaml
new file mode 100644
index 0000000000..52ffd92005
--- /dev/null
+++ b/test/conformance/kuttl/ttl/delete-twice/03-pod.yaml
@@ -0,0 +1,6 @@
+apiVersion: kuttl.dev/v1beta1
+kind: TestStep
+apply:
+- pod.yaml
+assert:
+- pod-assert.yaml
\ No newline at end of file
diff --git a/test/conformance/kuttl/ttl/delete-twice/04-check.yaml b/test/conformance/kuttl/ttl/delete-twice/04-check.yaml
new file mode 100644
index 0000000000..024ee4f1b4
--- /dev/null
+++ b/test/conformance/kuttl/ttl/delete-twice/04-check.yaml
@@ -0,0 +1,4 @@
+apiVersion: kuttl.dev/v1beta1
+kind: TestStep
+error:
+- pod-assert.yaml
\ No newline at end of file
diff --git a/test/conformance/kuttl/ttl/delete-twice/README.md b/test/conformance/kuttl/ttl/delete-twice/README.md
new file mode 100644
index 0000000000..fb565cce6e
--- /dev/null
+++ b/test/conformance/kuttl/ttl/delete-twice/README.md
@@ -0,0 +1,10 @@
+# ## Description
+
+This test cleans up pods via a label assignment named `cleanup.kyverno.io/ttl: 10s`.
+Once deleted, the pod is created a second time and we expect to be deleted again.
+
+## Expected Behavior
+
+The pod `test-pod` is cleaned up successfully after 10s twice.
+
+## Reference Issue(s)
diff --git a/test/conformance/kuttl/ttl/delete-twice/pod-assert.yaml b/test/conformance/kuttl/ttl/delete-twice/pod-assert.yaml
new file mode 100644
index 0000000000..06ec46e3f4
--- /dev/null
+++ b/test/conformance/kuttl/ttl/delete-twice/pod-assert.yaml
@@ -0,0 +1,6 @@
+apiVersion: v1
+kind: Pod
+metadata:
+  name: test-pod
+  labels:
+    cleanup.kyverno.io/ttl: 10s
\ No newline at end of file
diff --git a/test/conformance/kuttl/ttl/delete-twice/pod.yaml b/test/conformance/kuttl/ttl/delete-twice/pod.yaml
new file mode 100644
index 0000000000..5218083366
--- /dev/null
+++ b/test/conformance/kuttl/ttl/delete-twice/pod.yaml
@@ -0,0 +1,10 @@
+apiVersion: v1
+kind: Pod
+metadata:
+  name: test-pod
+  labels:
+    cleanup.kyverno.io/ttl: 10s
+spec:
+  containers:
+  - image: nginx:latest
+    name: nginx