diff --git a/flyteplugins/go/tasks/pluginmachinery/core/phase.go b/flyteplugins/go/tasks/pluginmachinery/core/phase.go
index 7847b161fc..6c80cc4d24 100644
--- a/flyteplugins/go/tasks/pluginmachinery/core/phase.go
+++ b/flyteplugins/go/tasks/pluginmachinery/core/phase.go
@@ -261,15 +261,15 @@ func PhaseInfoSuccess(info *TaskInfo) PhaseInfo {
 }
 
 func PhaseInfoSystemFailure(code, reason string, info *TaskInfo) PhaseInfo {
-	return PhaseInfoFailed(PhasePermanentFailure, &core.ExecutionError{Code: code, Message: reason, Kind: core.ExecutionError_SYSTEM}, info)
+	return phaseInfoFailed(PhasePermanentFailure, &core.ExecutionError{Code: code, Message: reason, Kind: core.ExecutionError_SYSTEM}, info, false)
 }
 
 func PhaseInfoSystemFailureWithCleanup(code, reason string, info *TaskInfo) PhaseInfo {
-	return phaseInfoFailed(PhasePermanentFailure, &core.ExecutionError{Code: code, Message: reason, Kind: core.ExecutionError_USER}, info, true)
+	return phaseInfoFailed(PhasePermanentFailure, &core.ExecutionError{Code: code, Message: reason, Kind: core.ExecutionError_SYSTEM}, info, true)
 }
 
 func PhaseInfoFailure(code, reason string, info *TaskInfo) PhaseInfo {
-	return PhaseInfoFailed(PhasePermanentFailure, &core.ExecutionError{Code: code, Message: reason, Kind: core.ExecutionError_USER}, info)
+	return phaseInfoFailed(PhasePermanentFailure, &core.ExecutionError{Code: code, Message: reason, Kind: core.ExecutionError_USER}, info, false)
 }
 
 func PhaseInfoFailureWithCleanup(code, reason string, info *TaskInfo) PhaseInfo {
@@ -277,7 +277,7 @@ func PhaseInfoFailureWithCleanup(code, reason string, info *TaskInfo) PhaseInfo
 }
 
 func PhaseInfoRetryableFailure(code, reason string, info *TaskInfo) PhaseInfo {
-	return PhaseInfoFailed(PhaseRetryableFailure, &core.ExecutionError{Code: code, Message: reason, Kind: core.ExecutionError_USER}, info)
+	return phaseInfoFailed(PhaseRetryableFailure, &core.ExecutionError{Code: code, Message: reason, Kind: core.ExecutionError_USER}, info, false)
 }
 
 func PhaseInfoRetryableFailureWithCleanup(code, reason string, info *TaskInfo) PhaseInfo {
@@ -285,7 +285,11 @@ func PhaseInfoRetryableFailureWithCleanup(code, reason string, info *TaskInfo) P
 }
 
 func PhaseInfoSystemRetryableFailure(code, reason string, info *TaskInfo) PhaseInfo {
-	return PhaseInfoFailed(PhaseRetryableFailure, &core.ExecutionError{Code: code, Message: reason, Kind: core.ExecutionError_SYSTEM}, info)
+	return phaseInfoFailed(PhaseRetryableFailure, &core.ExecutionError{Code: code, Message: reason, Kind: core.ExecutionError_SYSTEM}, info, false)
+}
+
+func PhaseInfoSystemRetryableFailureWithCleanup(code, reason string, info *TaskInfo) PhaseInfo {
+	return phaseInfoFailed(PhaseRetryableFailure, &core.ExecutionError{Code: code, Message: reason, Kind: core.ExecutionError_SYSTEM}, info, true)
 }
 
 // Creates a new PhaseInfo with phase set to PhaseWaitingForCache
diff --git a/flyteplugins/go/tasks/pluginmachinery/flytek8s/pod_helper.go b/flyteplugins/go/tasks/pluginmachinery/flytek8s/pod_helper.go
index 2f3447ad0e..2a17751c62 100644
--- a/flyteplugins/go/tasks/pluginmachinery/flytek8s/pod_helper.go
+++ b/flyteplugins/go/tasks/pluginmachinery/flytek8s/pod_helper.go
@@ -686,7 +686,7 @@ func demystifyPendingHelper(status v1.PodStatus) (pluginsCore.PhaseInfo, time.Ti
 
 								gracePeriod := config.GetK8sPluginConfig().CreateContainerErrorGracePeriod.Duration
 								if time.Since(t) >= gracePeriod {
-									return pluginsCore.PhaseInfoFailure(finalReason, GetMessageAfterGracePeriod(finalMessage, gracePeriod), &pluginsCore.TaskInfo{
+									return pluginsCore.PhaseInfoFailureWithCleanup(finalReason, GetMessageAfterGracePeriod(finalMessage, gracePeriod), &pluginsCore.TaskInfo{
 										OccurredAt: &t,
 									}), t
 								}
@@ -700,7 +700,7 @@ func demystifyPendingHelper(status v1.PodStatus) (pluginsCore.PhaseInfo, time.Ti
 							case "CreateContainerConfigError":
 								gracePeriod := config.GetK8sPluginConfig().CreateContainerConfigErrorGracePeriod.Duration
 								if time.Since(t) >= gracePeriod {
-									return pluginsCore.PhaseInfoFailure(finalReason, GetMessageAfterGracePeriod(finalMessage, gracePeriod), &pluginsCore.TaskInfo{
+									return pluginsCore.PhaseInfoFailureWithCleanup(finalReason, GetMessageAfterGracePeriod(finalMessage, gracePeriod), &pluginsCore.TaskInfo{
 										OccurredAt: &t,
 									}), t
 								}
@@ -712,7 +712,7 @@ func demystifyPendingHelper(status v1.PodStatus) (pluginsCore.PhaseInfo, time.Ti
 								), t
 
 							case "InvalidImageName":
-								return pluginsCore.PhaseInfoFailure(finalReason, finalMessage, &pluginsCore.TaskInfo{
+								return pluginsCore.PhaseInfoFailureWithCleanup(finalReason, finalMessage, &pluginsCore.TaskInfo{
 									OccurredAt: &t,
 								}), t
 
@@ -737,7 +737,7 @@ func demystifyPendingHelper(status v1.PodStatus) (pluginsCore.PhaseInfo, time.Ti
 								// by K8s and we get elusive 'pod not found' errors
 								// So be default if the container is not waiting with the PodInitializing/ContainerCreating
 								// reasons, then we will assume a failure reason, and fail instantly
-								return pluginsCore.PhaseInfoSystemRetryableFailure(finalReason, finalMessage, &pluginsCore.TaskInfo{
+								return pluginsCore.PhaseInfoSystemRetryableFailureWithCleanup(finalReason, finalMessage, &pluginsCore.TaskInfo{
 									OccurredAt: &t,
 								}), t
 							}
diff --git a/flyteplugins/go/tasks/pluginmachinery/flytek8s/pod_helper_test.go b/flyteplugins/go/tasks/pluginmachinery/flytek8s/pod_helper_test.go
index 925cb00186..b5a51323d2 100644
--- a/flyteplugins/go/tasks/pluginmachinery/flytek8s/pod_helper_test.go
+++ b/flyteplugins/go/tasks/pluginmachinery/flytek8s/pod_helper_test.go
@@ -1351,6 +1351,7 @@ func TestDemystifyPending(t *testing.T) {
 		taskStatus, err := DemystifyPending(s2)
 		assert.NoError(t, err)
 		assert.Equal(t, pluginsCore.PhaseRetryableFailure, taskStatus.Phase())
+		assert.True(t, taskStatus.CleanupOnFailure())
 	})
 
 	t.Run("InvalidImageName", func(t *testing.T) {
@@ -1368,6 +1369,7 @@ func TestDemystifyPending(t *testing.T) {
 		taskStatus, err := DemystifyPending(s)
 		assert.NoError(t, err)
 		assert.Equal(t, pluginsCore.PhasePermanentFailure, taskStatus.Phase())
+		assert.True(t, taskStatus.CleanupOnFailure())
 	})
 
 	t.Run("RegistryUnavailable", func(t *testing.T) {
@@ -1385,6 +1387,7 @@ func TestDemystifyPending(t *testing.T) {
 		taskStatus, err := DemystifyPending(s)
 		assert.NoError(t, err)
 		assert.Equal(t, pluginsCore.PhaseRetryableFailure, taskStatus.Phase())
+		assert.True(t, taskStatus.CleanupOnFailure())
 	})
 
 	t.Run("RandomError", func(t *testing.T) {
@@ -1402,6 +1405,7 @@ func TestDemystifyPending(t *testing.T) {
 		taskStatus, err := DemystifyPending(s)
 		assert.NoError(t, err)
 		assert.Equal(t, pluginsCore.PhaseRetryableFailure, taskStatus.Phase())
+		assert.True(t, taskStatus.CleanupOnFailure())
 	})
 
 	t.Run("CreateContainerConfigErrorWithinGracePeriod", func(t *testing.T) {
@@ -1440,6 +1444,7 @@ func TestDemystifyPending(t *testing.T) {
 		taskStatus, err := DemystifyPending(s2)
 		assert.NoError(t, err)
 		assert.Equal(t, pluginsCore.PhasePermanentFailure, taskStatus.Phase())
+		assert.True(t, taskStatus.CleanupOnFailure())
 	})
 
 	t.Run("CreateContainerErrorWithinGracePeriod", func(t *testing.T) {
@@ -1478,6 +1483,7 @@ func TestDemystifyPending(t *testing.T) {
 		taskStatus, err := DemystifyPending(s2)
 		assert.NoError(t, err)
 		assert.Equal(t, pluginsCore.PhasePermanentFailure, taskStatus.Phase())
+		assert.True(t, taskStatus.CleanupOnFailure())
 	})
 }
 
@@ -1510,6 +1516,7 @@ func TestDemystifyPendingTimeout(t *testing.T) {
 		assert.NoError(t, err)
 		assert.Equal(t, pluginsCore.PhaseRetryableFailure, taskStatus.Phase())
 		assert.Equal(t, "PodPendingTimeout", taskStatus.Err().Code)
+		assert.True(t, taskStatus.CleanupOnFailure())
 	})
 }