diff --git a/pkg/controller/deployment/deployment_controller.go b/pkg/controller/deployment/deployment_controller.go
index 6c6ee47a806..b1c63c0b06d 100644
--- a/pkg/controller/deployment/deployment_controller.go
+++ b/pkg/controller/deployment/deployment_controller.go
@@ -543,7 +543,26 @@ func (dc *DeploymentController) syncDeployment(key string) error {
 		return dc.syncStatusOnly(d)
 	}
 
-	err = dc.classifyReplicaSets(deployment)
+	// Why run the cleanup policy only when there is no rollback request?
+	// The thing with the cleanup policy currently is that it is far from smart because it takes into account
+	// the latest replica sets while it should instead retain the latest *working* replica sets. This means that
+	// you can have a cleanup policy of 1 but your last known working replica set may be 2 or 3 versions back
+	// in the history.
+	// Eventually we will want to find a way to recognize replica sets that have worked at some point in time
+	// (and chances are higher that they will work again as opposed to others that didn't) for candidates to
+	// automatically roll back to (#23211) and the cleanup policy should help.
+	if d.Spec.RollbackTo == nil {
+		_, oldRSs, err := dc.getAllReplicaSetsAndSyncRevision(d, false)
+		if err != nil {
+			return err
+		}
+		// So far the cleanup policy was executed once a deployment was paused, scaled up/down, or it
+		// succesfully completed deploying a replica set. Decouple it from the strategies and have it
+		// run almost unconditionally - cleanupDeployment is safe by default.
+		dc.cleanupDeployment(oldRSs, d)
+	}
+
+	err = dc.classifyReplicaSets(d)
 	if err != nil {
 		return err
 	}
diff --git a/pkg/controller/deployment/recreate.go b/pkg/controller/deployment/recreate.go
index 54e4290a9ff..3c3be85481e 100644
--- a/pkg/controller/deployment/recreate.go
+++ b/pkg/controller/deployment/recreate.go
@@ -73,8 +73,6 @@ func (dc *DeploymentController) rolloutRecreate(deployment *extensions.Deploymen
 		return dc.syncRolloutStatus(allRSs, newRS, deployment)
 	}
 
-	dc.cleanupDeployment(oldRSs, deployment)
-
 	// Sync deployment status
 	return dc.syncRolloutStatus(allRSs, newRS, deployment)
 }
diff --git a/pkg/controller/deployment/rolling.go b/pkg/controller/deployment/rolling.go
index 1c41508336f..d6ddf9da8ce 100644
--- a/pkg/controller/deployment/rolling.go
+++ b/pkg/controller/deployment/rolling.go
@@ -55,8 +55,6 @@ func (dc *DeploymentController) rolloutRolling(deployment *extensions.Deployment
 		return dc.syncRolloutStatus(allRSs, newRS, deployment)
 	}
 
-	dc.cleanupDeployment(oldRSs, deployment)
-
 	// Sync deployment status
 	return dc.syncRolloutStatus(allRSs, newRS, deployment)
 }
diff --git a/pkg/controller/deployment/sync.go b/pkg/controller/deployment/sync.go
index ba41759e04b..929a868e623 100644
--- a/pkg/controller/deployment/sync.go
+++ b/pkg/controller/deployment/sync.go
@@ -58,7 +58,6 @@ func (dc *DeploymentController) sync(deployment *extensions.Deployment) error {
 		// so we can abort this resync
 		return err
 	}
-	dc.cleanupDeployment(oldRSs, deployment)
 
 	allRSs := append(oldRSs, newRS)
 	return dc.syncDeploymentStatus(allRSs, newRS, deployment)