diff --git a/pkg/controller/deployment/deployment_controller.go b/pkg/controller/deployment/deployment_controller.go
index 091afe5ae0a..ac637347257 100644
--- a/pkg/controller/deployment/deployment_controller.go
+++ b/pkg/controller/deployment/deployment_controller.go
@@ -570,11 +570,11 @@ func (dc *DeploymentController) syncDeployment(key string) error {
 		return dc.sync(d)
 	}
 
+	// rollback is not re-entrant in case the underlying replica sets are updated with a new
+	// revision so we should ensure that we won't proceed to update replica sets until we
+	// make sure that the deployment has cleaned up its rollback spec in subsequent enqueues.
 	if d.Spec.RollbackTo != nil {
-		revision := d.Spec.RollbackTo.Revision
-		if d, err = dc.rollback(d, &revision); err != nil {
-			return err
-		}
+		return dc.rollback(d)
 	}
 
 	scalingEvent, err := dc.isScalingEvent(d)
diff --git a/pkg/controller/deployment/deployment_controller_test.go b/pkg/controller/deployment/deployment_controller_test.go
index cbd3181facd..7e63cf02915 100644
--- a/pkg/controller/deployment/deployment_controller_test.go
+++ b/pkg/controller/deployment/deployment_controller_test.go
@@ -17,7 +17,6 @@ limitations under the License.
 package deployment
 
 import (
-	"fmt"
 	"testing"
 	"time"
 
@@ -109,11 +108,13 @@ func newDeployment(name string, replicas int, revisionHistoryLimit *int32, maxSu
 }
 
 func newReplicaSet(d *extensions.Deployment, name string, replicas int) *extensions.ReplicaSet {
+	control := true
 	return &extensions.ReplicaSet{
 		ObjectMeta: metav1.ObjectMeta{
-			Name:      name,
-			Namespace: metav1.NamespaceDefault,
-			Labels:    d.Spec.Selector.MatchLabels,
+			Name:            name,
+			Namespace:       metav1.NamespaceDefault,
+			Labels:          d.Spec.Selector.MatchLabels,
+			OwnerReferences: []metav1.OwnerReference{{APIVersion: getDeploymentKind().GroupVersion().Version, Kind: getDeploymentKind().Kind, Name: d.Name, UID: d.UID, Controller: &control}},
 		},
 		Spec: extensions.ReplicaSetSpec{
 			Selector: d.Spec.Selector,
@@ -153,6 +154,11 @@ func (f *fixture) expectUpdateDeploymentStatusAction(d *extensions.Deployment) {
 	f.actions = append(f.actions, action)
 }
 
+func (f *fixture) expectUpdateDeploymentAction(d *extensions.Deployment) {
+	action := core.NewUpdateAction(schema.GroupVersionResource{Resource: "deployments"}, d.Namespace, d)
+	f.actions = append(f.actions, action)
+}
+
 func (f *fixture) expectCreateRSAction(rs *extensions.ReplicaSet) {
 	f.actions = append(f.actions, core.NewCreateAction(schema.GroupVersionResource{Resource: "replicasets"}, rs.Namespace, rs))
 }
@@ -214,6 +220,24 @@ func (f *fixture) run(deploymentName string) {
 	}
 }
 
+func filterInformerActions(actions []core.Action) []core.Action {
+	ret := []core.Action{}
+	for _, action := range actions {
+		if len(action.GetNamespace()) == 0 &&
+			(action.Matches("list", "pods") ||
+				action.Matches("list", "deployments") ||
+				action.Matches("list", "replicasets") ||
+				action.Matches("watch", "pods") ||
+				action.Matches("watch", "deployments") ||
+				action.Matches("watch", "replicasets")) {
+			continue
+		}
+		ret = append(ret, action)
+	}
+
+	return ret
+}
+
 func TestSyncDeploymentCreatesReplicaSet(t *testing.T) {
 	f := newFixture(t)
 
@@ -244,53 +268,47 @@ func TestSyncDeploymentDontDoAnythingDuringDeletion(t *testing.T) {
 }
 
 // issue: https://github.com/kubernetes/kubernetes/issues/23218
-func TestDeploymentController_dontSyncDeploymentsWithEmptyPodSelector(t *testing.T) {
-	fake := &fake.Clientset{}
-	informers := informers.NewSharedInformerFactory(fake, controller.NoResyncPeriodFunc())
-	controller := NewDeploymentController(informers.Extensions().V1beta1().Deployments(), informers.Extensions().V1beta1().ReplicaSets(), informers.Core().V1().Pods(), fake)
-	controller.eventRecorder = &record.FakeRecorder{}
-	controller.dListerSynced = alwaysReady
-	controller.rsListerSynced = alwaysReady
-	controller.podListerSynced = alwaysReady
-
-	stopCh := make(chan struct{})
-	defer close(stopCh)
-	informers.Start(stopCh)
+func TestDontSyncDeploymentsWithEmptyPodSelector(t *testing.T) {
+	f := newFixture(t)
 
 	d := newDeployment("foo", 1, nil, nil, nil, map[string]string{"foo": "bar"})
-	empty := metav1.LabelSelector{}
-	d.Spec.Selector = &empty
-	informers.Extensions().V1beta1().Deployments().Informer().GetIndexer().Add(d)
-	// We expect the deployment controller to not take action here since it's configuration
-	// is invalid, even though no replicasets exist that match it's selector.
-	controller.syncDeployment(fmt.Sprintf("%s/%s", d.ObjectMeta.Namespace, d.ObjectMeta.Name))
+	d.Spec.Selector = &metav1.LabelSelector{}
+	f.dLister = append(f.dLister, d)
+	f.objects = append(f.objects, d)
 
-	filteredActions := filterInformerActions(fake.Actions())
-	if len(filteredActions) == 0 {
-		return
-	}
-	for _, action := range filteredActions {
-		t.Logf("unexpected action: %#v", action)
-	}
-	t.Errorf("expected deployment controller to not take action")
+	// Normally there should be a status update to sync observedGeneration but the fake
+	// deployment has no generation set so there is no action happpening here.
+	f.run(getKey(d, t))
 }
 
-func filterInformerActions(actions []core.Action) []core.Action {
-	ret := []core.Action{}
-	for _, action := range actions {
-		if len(action.GetNamespace()) == 0 &&
-			(action.Matches("list", "pods") ||
-				action.Matches("list", "deployments") ||
-				action.Matches("list", "replicasets") ||
-				action.Matches("watch", "pods") ||
-				action.Matches("watch", "deployments") ||
-				action.Matches("watch", "replicasets")) {
-			continue
-		}
-		ret = append(ret, action)
-	}
+func TestReentrantRollback(t *testing.T) {
+	f := newFixture(t)
 
-	return ret
+	d := newDeployment("foo", 1, nil, nil, nil, map[string]string{"foo": "bar"})
+
+	d.Spec.RollbackTo = &extensions.RollbackConfig{Revision: 0}
+	// TODO: This is 1 for now until FindOldReplicaSets gets fixed.
+	// See https://github.com/kubernetes/kubernetes/issues/42570.
+	d.Annotations = map[string]string{util.RevisionAnnotation: "1"}
+	f.dLister = append(f.dLister, d)
+
+	rs1 := newReplicaSet(d, "deploymentrs-old", 0)
+	rs1.Annotations = map[string]string{util.RevisionAnnotation: "1"}
+	one := int64(1)
+	rs1.Spec.Template.Spec.TerminationGracePeriodSeconds = &one
+	rs1.Spec.Selector.MatchLabels[extensions.DefaultDeploymentUniqueLabelKey] = "hash"
+
+	rs2 := newReplicaSet(d, "deploymentrs-new", 1)
+	rs2.Annotations = map[string]string{util.RevisionAnnotation: "2"}
+	rs2.Spec.Selector.MatchLabels[extensions.DefaultDeploymentUniqueLabelKey] = "hash"
+
+	f.rsLister = append(f.rsLister, rs1, rs2)
+	f.objects = append(f.objects, d, rs1, rs2)
+
+	// Rollback is done here
+	f.expectUpdateDeploymentAction(d)
+	// Expect no update on replica sets though
+	f.run(getKey(d, t))
 }
 
 // TestOverlappingDeployment ensures that an overlapping deployment will not be synced by
diff --git a/pkg/controller/deployment/rollback.go b/pkg/controller/deployment/rollback.go
index 0d7263a2a27..68cec72f569 100644
--- a/pkg/controller/deployment/rollback.go
+++ b/pkg/controller/deployment/rollback.go
@@ -20,25 +20,28 @@ import (
 	"fmt"
 
 	"github.com/golang/glog"
+
 	"k8s.io/kubernetes/pkg/api/v1"
 	extensions "k8s.io/kubernetes/pkg/apis/extensions/v1beta1"
 	deploymentutil "k8s.io/kubernetes/pkg/controller/deployment/util"
 )
 
-// Rolling back to a revision; no-op if the toRevision is deployment's current revision
-func (dc *DeploymentController) rollback(deployment *extensions.Deployment, toRevision *int64) (*extensions.Deployment, error) {
-	newRS, allOldRSs, err := dc.getAllReplicaSetsAndSyncRevision(deployment, true)
+// rollback the deployment to the specified revision. In any case cleanup the rollback spec.
+func (dc *DeploymentController) rollback(d *extensions.Deployment) error {
+	newRS, allOldRSs, err := dc.getAllReplicaSetsAndSyncRevision(d, true)
 	if err != nil {
-		return nil, err
+		return err
 	}
+
 	allRSs := append(allOldRSs, newRS)
+	toRevision := &d.Spec.RollbackTo.Revision
 	// If rollback revision is 0, rollback to the last revision
 	if *toRevision == 0 {
 		if *toRevision = deploymentutil.LastRevision(allRSs); *toRevision == 0 {
 			// If we still can't find the last revision, gives up rollback
-			dc.emitRollbackWarningEvent(deployment, deploymentutil.RollbackRevisionNotFound, "Unable to find last revision.")
+			dc.emitRollbackWarningEvent(d, deploymentutil.RollbackRevisionNotFound, "Unable to find last revision.")
 			// Gives up rollback
-			return dc.updateDeploymentAndClearRollbackTo(deployment)
+			return dc.updateDeploymentAndClearRollbackTo(d)
 		}
 	}
 	for _, rs := range allRSs {
@@ -52,22 +55,26 @@ func (dc *DeploymentController) rollback(deployment *extensions.Deployment, toRe
 			// rollback by copying podTemplate.Spec from the replica set
 			// revision number will be incremented during the next getAllReplicaSetsAndSyncRevision call
 			// no-op if the the spec matches current deployment's podTemplate.Spec
-			deployment, performedRollback, err := dc.rollbackToTemplate(deployment, rs)
+			performedRollback, err := dc.rollbackToTemplate(d, rs)
 			if performedRollback && err == nil {
-				dc.emitRollbackNormalEvent(deployment, fmt.Sprintf("Rolled back deployment %q to revision %d", deployment.Name, *toRevision))
+				dc.emitRollbackNormalEvent(d, fmt.Sprintf("Rolled back deployment %q to revision %d", d.Name, *toRevision))
 			}
-			return deployment, err
+			return err
 		}
 	}
-	dc.emitRollbackWarningEvent(deployment, deploymentutil.RollbackRevisionNotFound, "Unable to find the revision to rollback to.")
+	dc.emitRollbackWarningEvent(d, deploymentutil.RollbackRevisionNotFound, "Unable to find the revision to rollback to.")
 	// Gives up rollback
-	return dc.updateDeploymentAndClearRollbackTo(deployment)
+	return dc.updateDeploymentAndClearRollbackTo(d)
 }
 
-func (dc *DeploymentController) rollbackToTemplate(deployment *extensions.Deployment, rs *extensions.ReplicaSet) (d *extensions.Deployment, performedRollback bool, err error) {
-	if !deploymentutil.EqualIgnoreHash(deployment.Spec.Template, rs.Spec.Template) {
-		glog.V(4).Infof("Rolling back deployment %q to template spec %+v", deployment.Name, rs.Spec.Template.Spec)
-		deploymentutil.SetFromReplicaSetTemplate(deployment, rs.Spec.Template)
+// rollbackToTemplate compares the templates of the provided deployment and replica set and
+// updates the deployment with the replica set template in case they are different. It also
+// cleans up the rollback spec so subsequent requeues of the deployment won't end up in here.
+func (dc *DeploymentController) rollbackToTemplate(d *extensions.Deployment, rs *extensions.ReplicaSet) (bool, error) {
+	performedRollback := false
+	if !deploymentutil.EqualIgnoreHash(d.Spec.Template, rs.Spec.Template) {
+		glog.V(4).Infof("Rolling back deployment %q to template spec %+v", d.Name, rs.Spec.Template.Spec)
+		deploymentutil.SetFromReplicaSetTemplate(d, rs.Spec.Template)
 		// set RS (the old RS we'll rolling back to) annotations back to the deployment;
 		// otherwise, the deployment's current annotations (should be the same as current new RS) will be copied to the RS after the rollback.
 		//
@@ -79,27 +86,31 @@ func (dc *DeploymentController) rollbackToTemplate(deployment *extensions.Deploy
 		//
 		// If we don't copy the annotations back from RS to deployment on rollback, the Deployment will stay as {change-cause:edit},
 		// and new RS1 becomes {change-cause:edit} (copied from deployment after rollback), old RS2 {change-cause:edit}, which is not correct.
-		deploymentutil.SetDeploymentAnnotationsTo(deployment, rs)
+		deploymentutil.SetDeploymentAnnotationsTo(d, rs)
 		performedRollback = true
 	} else {
-		glog.V(4).Infof("Rolling back to a revision that contains the same template as current deployment %s, skipping rollback...", deployment.Name)
-		dc.emitRollbackWarningEvent(deployment, deploymentutil.RollbackTemplateUnchanged, fmt.Sprintf("The rollback revision contains the same template as current deployment %q", deployment.Name))
+		glog.V(4).Infof("Rolling back to a revision that contains the same template as current deployment %q, skipping rollback...", d.Name)
+		eventMsg := fmt.Sprintf("The rollback revision contains the same template as current deployment %q", d.Name)
+		dc.emitRollbackWarningEvent(d, deploymentutil.RollbackTemplateUnchanged, eventMsg)
 	}
-	d, err = dc.updateDeploymentAndClearRollbackTo(deployment)
-	return
+
+	return performedRollback, dc.updateDeploymentAndClearRollbackTo(d)
 }
 
-func (dc *DeploymentController) emitRollbackWarningEvent(deployment *extensions.Deployment, reason, message string) {
-	dc.eventRecorder.Eventf(deployment, v1.EventTypeWarning, reason, message)
+func (dc *DeploymentController) emitRollbackWarningEvent(d *extensions.Deployment, reason, message string) {
+	dc.eventRecorder.Eventf(d, v1.EventTypeWarning, reason, message)
 }
 
-func (dc *DeploymentController) emitRollbackNormalEvent(deployment *extensions.Deployment, message string) {
-	dc.eventRecorder.Eventf(deployment, v1.EventTypeNormal, deploymentutil.RollbackDone, message)
+func (dc *DeploymentController) emitRollbackNormalEvent(d *extensions.Deployment, message string) {
+	dc.eventRecorder.Eventf(d, v1.EventTypeNormal, deploymentutil.RollbackDone, message)
 }
 
 // updateDeploymentAndClearRollbackTo sets .spec.rollbackTo to nil and update the input deployment
-func (dc *DeploymentController) updateDeploymentAndClearRollbackTo(deployment *extensions.Deployment) (*extensions.Deployment, error) {
-	glog.V(4).Infof("Cleans up rollbackTo of deployment %s", deployment.Name)
-	deployment.Spec.RollbackTo = nil
-	return dc.client.Extensions().Deployments(deployment.ObjectMeta.Namespace).Update(deployment)
+// It is assumed that the caller will have updated the deployment template appropriately (in case
+// we want to rollback).
+func (dc *DeploymentController) updateDeploymentAndClearRollbackTo(d *extensions.Deployment) error {
+	glog.V(4).Infof("Cleans up rollbackTo of deployment %q", d.Name)
+	d.Spec.RollbackTo = nil
+	_, err := dc.client.Extensions().Deployments(d.Namespace).Update(d)
+	return err
 }
diff --git a/pkg/controller/deployment/util/deployment_util.go b/pkg/controller/deployment/util/deployment_util.go
index 4aa70fa1a8f..b3705b02c6b 100644
--- a/pkg/controller/deployment/util/deployment_util.go
+++ b/pkg/controller/deployment/util/deployment_util.go
@@ -650,6 +650,7 @@ func FindOldReplicaSets(deployment *extensions.Deployment, rsList []*extensions.
 			if newRS != nil && rs.UID == newRS.UID {
 				continue
 			}
+			// TODO: If there are no pods for a deployment, we will never return old replica sets....!
 			allOldRSs[rs.ObjectMeta.Name] = rs
 			if rsLabelsSelector.Matches(podLabelsSelector) {
 				oldRSs[rs.ObjectMeta.Name] = rs