diff --git a/pkg/apis/pipeline/v1beta1/taskrun_types.go b/pkg/apis/pipeline/v1beta1/taskrun_types.go
index a314760bcef..d5fb6fe9b8a 100644
--- a/pkg/apis/pipeline/v1beta1/taskrun_types.go
+++ b/pkg/apis/pipeline/v1beta1/taskrun_types.go
@@ -156,6 +156,8 @@ func (trs *TaskRunStatus) MarkResourceFailed(reason TaskRunReason, err error) {
 		Reason:  reason.String(),
 		Message: err.Error(),
 	})
+	succeeded := trs.GetCondition(apis.ConditionSucceeded)
+	trs.CompletionTime = &succeeded.LastTransitionTime.Inner
 }
 
 // TaskRunStatusFields holds the fields of TaskRun's status.  This is defined
diff --git a/pkg/reconciler/taskrun/taskrun.go b/pkg/reconciler/taskrun/taskrun.go
index 19c29f51b17..048c2962f08 100644
--- a/pkg/reconciler/taskrun/taskrun.go
+++ b/pkg/reconciler/taskrun/taskrun.go
@@ -24,6 +24,8 @@ import (
 	"strings"
 	"time"
 
+	"go.uber.org/zap"
+
 	"github.com/ghodss/yaml"
 	"github.com/hashicorp/go-multierror"
 	"github.com/tektoncd/pipeline/pkg/apis/config"
@@ -103,54 +105,46 @@ func (c *Reconciler) ReconcileKind(ctx context.Context, tr *v1beta1.TaskRun) pkg
 		// on the event to perform user facing initialisations, such has reset a CI check status
 		afterCondition := tr.Status.GetCondition(apis.ConditionSucceeded)
 		events.Emit(ctx, nil, afterCondition, tr)
+
+		// We already sent an event for start, so update `before` with the current status
+		before = tr.Status.GetCondition(apis.ConditionSucceeded)
 	}
 
 	// If the TaskRun is complete, run some post run fixtures when applicable
 	if tr.IsDone() {
 		logger.Infof("taskrun done : %s \n", tr.Name)
-		var merr *multierror.Error
+
+		// We may be reading a version of the object that was stored at an older version
+		// and may not have had all of the assumed default specified.
+		tr.SetDefaults(contexts.WithUpgradeViaDefaulting(ctx))
+
 		// Try to send cloud events first
 		cloudEventErr := cloudevent.SendCloudEvents(tr, c.cloudEventClient, logger)
 		// Regardless of `err`, we must write back any status update that may have
 		// been generated by `sendCloudEvents`
-		_, updateErr := c.updateLabelsAndAnnotations(tr)
-		merr = multierror.Append(cloudEventErr, updateErr)
 		if cloudEventErr != nil {
 			// Let's keep timeouts and sidecars running as long as we're trying to
 			// send cloud events. So we stop here an return errors encountered this far.
-			return merr.ErrorOrNil()
+			return cloudEventErr
 		}
+
 		c.timeoutHandler.Release(tr)
-		pod, err := c.KubeClientSet.CoreV1().Pods(tr.Namespace).Get(tr.Status.PodName, metav1.GetOptions{})
-		if err == nil {
-			err = podconvert.StopSidecars(c.Images.NopImage, c.KubeClientSet, *pod)
-			if err == nil {
-				// Check if any SidecarStatuses are still shown as Running after stopping
-				// Sidecars. If any Running, update SidecarStatuses based on Pod ContainerStatuses.
-				if podconvert.IsSidecarStatusRunning(tr) {
-					err = updateStoppedSidecarStatus(ctx, pod, tr, c)
-				}
-			}
-		} else if k8serrors.IsNotFound(err) {
-			return merr.ErrorOrNil()
-		}
-		if err != nil {
-			logger.Errorf("Error stopping sidecars for TaskRun %q: %v", tr.Name, err)
-			merr = multierror.Append(merr, err)
-		}
+
+		pod := c.stopSidecars(ctx, tr)
 
 		go func(metrics *Recorder) {
 			err := metrics.DurationAndCount(tr)
 			if err != nil {
 				logger.Warnf("Failed to log the metrics : %v", err)
 			}
-			err = metrics.RecordPodLatency(pod, tr)
-			if err != nil {
-				logger.Warnf("Failed to log the metrics : %v", err)
+			if pod != nil {
+				err = metrics.RecordPodLatency(pod, tr)
+				if err != nil {
+					logger.Warnf("Failed to log the metrics : %v", err)
+				}
 			}
 		}(c.metrics)
-
-		return merr.ErrorOrNil()
+		return c.finishReconcileUpdateEmitEvents(ctx, tr, before, nil)
 	}
 
 	// If the TaskRun is cancelled, kill resources and update status
@@ -176,12 +170,9 @@ func (c *Reconciler) ReconcileKind(ctx context.Context, tr *v1beta1.TaskRun) pkg
 		logger.Errorf("TaskRun prepare error: %v", err.Error())
 		// We only return an error if update failed, otherwise we don't want to
 		// reconcile an invalid TaskRun anymore
-		return c.finishReconcileUpdateEmitEvents(ctx, tr, nil, err)
+		return c.finishReconcileUpdateEmitEvents(ctx, tr, before, err)
 	}
 
-	// Store the condition before reconcile
-	before = tr.Status.GetCondition(apis.ConditionSucceeded)
-
 	// Reconcile this copy of the task run and then write back any status
 	// updates regardless of whether the reconciliation errored out.
 	if err = c.reconcile(ctx, tr, taskSpec, rtr); err != nil {
@@ -190,8 +181,32 @@ func (c *Reconciler) ReconcileKind(ctx context.Context, tr *v1beta1.TaskRun) pkg
 	// Emit events (only when ConditionSucceeded was changed)
 	return c.finishReconcileUpdateEmitEvents(ctx, tr, before, err)
 }
+func (c *Reconciler) stopSidecars(ctx context.Context, tr *v1beta1.TaskRun) *corev1.Pod {
+	logger := logging.FromContext(ctx)
+	if tr.Status.PodName == "" {
+		return nil
+	}
+	pod, err := c.KubeClientSet.CoreV1().Pods(tr.Namespace).Get(tr.Status.PodName, metav1.GetOptions{})
+	if err == nil {
+		err = podconvert.StopSidecars(c.Images.NopImage, c.KubeClientSet, *pod)
+		if err == nil {
+			// Check if any SidecarStatuses are still shown as Running after stopping
+			// Sidecars. If any Running, update SidecarStatuses based on Pod ContainerStatuses.
+			if podconvert.IsSidecarStatusRunning(tr) {
+				err = updateStoppedSidecarStatus(ctx, pod, tr, c)
+			}
+		}
+	}
+	if err != nil {
+		logger.Errorf("Error stopping sidecars for TaskRun %q: %v", tr.Name, err)
+		tr.Status.MarkResourceFailed(podconvert.ReasonFailedResolution, err)
+	}
+	return pod
+}
 
 func (c *Reconciler) finishReconcileUpdateEmitEvents(ctx context.Context, tr *v1beta1.TaskRun, beforeCondition *apis.Condition, previousError error) error {
+	logger := logging.FromContext(ctx)
+
 	afterCondition := tr.Status.GetCondition(apis.ConditionSucceeded)
 
 	// Send k8s events and cloud events (when configured)
@@ -199,12 +214,15 @@ func (c *Reconciler) finishReconcileUpdateEmitEvents(ctx context.Context, tr *v1
 
 	_, err := c.updateLabelsAndAnnotations(tr)
 	if err != nil {
+		logger.Warn("Failed to update PipelineRun labels/annotations", zap.Error(err))
 		events.EmitError(controller.GetEventRecorder(ctx), err, tr)
 	}
+
+	merr := multierror.Append(previousError, err).ErrorOrNil()
 	if controller.IsPermanentError(previousError) {
-		return controller.NewPermanentError(multierror.Append(previousError, err))
+		return controller.NewPermanentError(merr)
 	}
-	return multierror.Append(previousError, err).ErrorOrNil()
+	return merr
 }
 
 func (c *Reconciler) getTaskResolver(tr *v1beta1.TaskRun) (*resources.LocalTaskRefResolver, v1beta1.TaskKind) {
diff --git a/pkg/reconciler/taskrun/taskrun_test.go b/pkg/reconciler/taskrun/taskrun_test.go
index 7ad27d2f3f3..2f5a21a3f1f 100644
--- a/pkg/reconciler/taskrun/taskrun_test.go
+++ b/pkg/reconciler/taskrun/taskrun_test.go
@@ -39,7 +39,7 @@ import (
 	"github.com/tektoncd/pipeline/pkg/system"
 	"github.com/tektoncd/pipeline/pkg/timeout"
 	"github.com/tektoncd/pipeline/pkg/workspace"
-	test "github.com/tektoncd/pipeline/test"
+	"github.com/tektoncd/pipeline/test"
 	"github.com/tektoncd/pipeline/test/diff"
 	"github.com/tektoncd/pipeline/test/names"
 	corev1 "k8s.io/api/core/v1"
@@ -1733,6 +1733,57 @@ func TestReconcileInvalidTaskRuns(t *testing.T) {
 
 }
 
+func TestReconcileTaskRunWithPermanentError(t *testing.T) {
+	noTaskRun := tb.TaskRun("notaskrun", tb.TaskRunNamespace("foo"), tb.TaskRunSpec(tb.TaskRunTaskRef("notask")),
+		tb.TaskRunStatus(tb.TaskRunStartTime(time.Now()),
+			tb.StatusCondition(apis.Condition{
+				Type:    apis.ConditionSucceeded,
+				Status:  corev1.ConditionFalse,
+				Reason:  podconvert.ReasonFailedResolution,
+				Message: "error when listing tasks for taskRun taskrun-failure: tasks.tekton.dev \"notask\" not found",
+			})))
+
+	taskRuns := []*v1beta1.TaskRun{noTaskRun}
+
+	d := test.Data{
+		TaskRuns: taskRuns,
+	}
+
+	testAssets, cancel := getTaskRunController(t, d)
+	defer cancel()
+	c := testAssets.Controller
+	clients := testAssets.Clients
+	reconcileErr := c.Reconciler.Reconcile(context.Background(), getRunName(noTaskRun))
+
+	// When a TaskRun was rejected with a permanent error, reconciler must stop and forget about the run
+	// Such TaskRun enters Reconciler and from within the isDone block, marks the run success so that
+	// reconciler does not keep trying to reconcile
+	if reconcileErr != nil {
+		t.Fatalf("Expected to see no error when reconciling TaskRun with Permanent Error but was not none")
+	}
+
+	// Check actions
+	actions := clients.Kube.Actions()
+	if len(actions) != 3 || actions[0].Matches("namespaces", "list") {
+		t.Errorf("expected 3 actions (list namespaces, list configmaps, and watch configmaps) created by the reconciler,"+
+			" got %d. Actions: %#v", len(actions), actions)
+	}
+
+	newTr, err := clients.Pipeline.TektonV1beta1().TaskRuns(noTaskRun.Namespace).Get(noTaskRun.Name, metav1.GetOptions{})
+	if err != nil {
+		t.Fatalf("Expected TaskRun %s to exist but instead got error when getting it: %v", noTaskRun.Name, err)
+	}
+
+	// Since the TaskRun is invalid, the status should say it has failed
+	condition := newTr.Status.GetCondition(apis.ConditionSucceeded)
+	if condition == nil || condition.Status != corev1.ConditionFalse {
+		t.Errorf("Expected invalid TaskRun to have failed status, but had %v", condition)
+	}
+	if condition != nil && condition.Reason != podconvert.ReasonFailedResolution {
+		t.Errorf("Expected failure to be because of reason %q but was %s", podconvert.ReasonFailedResolution, condition.Reason)
+	}
+}
+
 func TestReconcilePodFetchError(t *testing.T) {
 	taskRun := tb.TaskRun("test-taskrun-run-success",
 		tb.TaskRunNamespace("foo"),