diff --git a/pkg/canary/config_tracker_test.go b/pkg/canary/config_tracker_test.go
index cc2ebab42..edb88d1e5 100644
--- a/pkg/canary/config_tracker_test.go
+++ b/pkg/canary/config_tracker_test.go
@@ -124,7 +124,7 @@ func TestConfigTracker_ConfigMaps(t *testing.T) {
 		configMap := newDaemonSetControllerTestConfigMap()
 		configMapProjected := newDaemonSetControllerTestConfigProjected()
 
-		err := mocks.controller.Initialize(mocks.canary)
+		_, err := mocks.controller.Initialize(mocks.canary)
 		require.NoError(t, err)
 
 		daePrimary, err := mocks.kubeClient.AppsV1().DaemonSets("default").Get(context.TODO(), "podinfo-primary", metav1.GetOptions{})
diff --git a/pkg/canary/controller.go b/pkg/canary/controller.go
index 86241d4ea..62c86470f 100644
--- a/pkg/canary/controller.go
+++ b/pkg/canary/controller.go
@@ -21,7 +21,7 @@ import (
 )
 
 type Controller interface {
-	IsPrimaryReady(canary *flaggerv1.Canary) error
+	IsPrimaryReady(canary *flaggerv1.Canary) (bool, error)
 	IsCanaryReady(canary *flaggerv1.Canary) (bool, error)
 	GetMetadata(canary *flaggerv1.Canary) (string, string, map[string]int32, error)
 	SyncStatus(canary *flaggerv1.Canary, status flaggerv1.CanaryStatus) error
@@ -29,7 +29,7 @@ type Controller interface {
 	SetStatusWeight(canary *flaggerv1.Canary, val int) error
 	SetStatusIterations(canary *flaggerv1.Canary, val int) error
 	SetStatusPhase(canary *flaggerv1.Canary, phase flaggerv1.CanaryPhase) error
-	Initialize(canary *flaggerv1.Canary) error
+	Initialize(canary *flaggerv1.Canary) (bool, error)
 	Promote(canary *flaggerv1.Canary) error
 	HasTargetChanged(canary *flaggerv1.Canary) (bool, error)
 	HaveDependenciesChanged(canary *flaggerv1.Canary) (bool, error)
diff --git a/pkg/canary/daemonset_controller.go b/pkg/canary/daemonset_controller.go
index 026c243e4..5b8f92e87 100644
--- a/pkg/canary/daemonset_controller.go
+++ b/pkg/canary/daemonset_controller.go
@@ -92,21 +92,21 @@ func (c *DaemonSetController) ScaleFromZero(cd *flaggerv1.Canary) error {
 }
 
 // Initialize creates the primary DaemonSet if it does not exist.
-func (c *DaemonSetController) Initialize(cd *flaggerv1.Canary) (err error) {
-	err = c.createPrimaryDaemonSet(cd, c.includeLabelPrefix)
+func (c *DaemonSetController) Initialize(cd *flaggerv1.Canary) (bool, error) {
+	err := c.createPrimaryDaemonSet(cd, c.includeLabelPrefix)
 	if err != nil {
-		return fmt.Errorf("createPrimaryDaemonSet failed: %w", err)
+		return true, fmt.Errorf("createPrimaryDaemonSet failed: %w", err)
 	}
 
 	if cd.Status.Phase == "" || cd.Status.Phase == flaggerv1.CanaryPhaseInitializing {
 		if !cd.SkipAnalysis() {
-			if err := c.IsPrimaryReady(cd); err != nil {
-				return fmt.Errorf("%w", err)
+			if retriable, err := c.IsPrimaryReady(cd); err != nil {
+				return retriable, fmt.Errorf("%w", err)
 			}
 		}
 	}
 
-	return nil
+	return true, nil
 }
 
 // Promote copies the pod spec, secrets and config maps from canary to primary
diff --git a/pkg/canary/daemonset_controller_test.go b/pkg/canary/daemonset_controller_test.go
index f886955da..f3f73eb97 100644
--- a/pkg/canary/daemonset_controller_test.go
+++ b/pkg/canary/daemonset_controller_test.go
@@ -34,7 +34,7 @@ import (
 func TestDaemonSetController_Sync_ConsistentNaming(t *testing.T) {
 	dc := daemonsetConfigs{name: "podinfo", label: "name", labelValue: "podinfo"}
 	mocks := newDaemonSetFixture(dc)
-	err := mocks.controller.Initialize(mocks.canary)
+	_, err := mocks.controller.Initialize(mocks.canary)
 	require.NoError(t, err)
 
 	daePrimary, err := mocks.kubeClient.AppsV1().DaemonSets("default").Get(context.TODO(), fmt.Sprintf("%s-primary", dc.name), metav1.GetOptions{})
@@ -56,7 +56,7 @@ func TestDaemonSetController_Sync_ConsistentNaming(t *testing.T) {
 func TestDaemonSetController_Sync_InconsistentNaming(t *testing.T) {
 	dc := daemonsetConfigs{name: "podinfo-service", label: "name", labelValue: "podinfo"}
 	mocks := newDaemonSetFixture(dc)
-	err := mocks.controller.Initialize(mocks.canary)
+	_, err := mocks.controller.Initialize(mocks.canary)
 	require.NoError(t, err)
 
 	daePrimary, err := mocks.kubeClient.AppsV1().DaemonSets("default").Get(context.TODO(), fmt.Sprintf("%s-primary", dc.name), metav1.GetOptions{})
@@ -75,7 +75,7 @@ func TestDaemonSetController_Sync_InconsistentNaming(t *testing.T) {
 func TestDaemonSetController_Promote(t *testing.T) {
 	dc := daemonsetConfigs{name: "podinfo", label: "name", labelValue: "podinfo"}
 	mocks := newDaemonSetFixture(dc)
-	err := mocks.controller.Initialize(mocks.canary)
+	_, err := mocks.controller.Initialize(mocks.canary)
 	require.NoError(t, err)
 
 	dae2 := newDaemonSetControllerTestPodInfoV2()
@@ -116,7 +116,7 @@ func TestDaemonSetController_NoConfigTracking(t *testing.T) {
 	mocks := newDaemonSetFixture(dc)
 	mocks.controller.configTracker = &NopTracker{}
 
-	err := mocks.controller.Initialize(mocks.canary)
+	_, err := mocks.controller.Initialize(mocks.canary)
 	require.NoError(t, err)
 
 	daePrimary, err := mocks.kubeClient.AppsV1().DaemonSets("default").Get(context.TODO(), "podinfo-primary", metav1.GetOptions{})
@@ -132,7 +132,7 @@ func TestDaemonSetController_NoConfigTracking(t *testing.T) {
 func TestDaemonSetController_HasTargetChanged(t *testing.T) {
 	dc := daemonsetConfigs{name: "podinfo", label: "name", labelValue: "podinfo"}
 	mocks := newDaemonSetFixture(dc)
-	err := mocks.controller.Initialize(mocks.canary)
+	_, err := mocks.controller.Initialize(mocks.canary)
 	require.NoError(t, err)
 
 	// save last applied hash
@@ -221,7 +221,7 @@ func TestDaemonSetController_Scale(t *testing.T) {
 	t.Run("ScaleToZero", func(t *testing.T) {
 		dc := daemonsetConfigs{name: "podinfo", label: "name", labelValue: "podinfo"}
 		mocks := newDaemonSetFixture(dc)
-		err := mocks.controller.Initialize(mocks.canary)
+		_, err := mocks.controller.Initialize(mocks.canary)
 		require.NoError(t, err)
 
 		err = mocks.controller.ScaleToZero(mocks.canary)
@@ -238,7 +238,7 @@ func TestDaemonSetController_Scale(t *testing.T) {
 	t.Run("ScaleFromZeo", func(t *testing.T) {
 		dc := daemonsetConfigs{name: "podinfo", label: "name", labelValue: "podinfo"}
 		mocks := newDaemonSetFixture(dc)
-		err := mocks.controller.Initialize(mocks.canary)
+		_, err := mocks.controller.Initialize(mocks.canary)
 		require.NoError(t, err)
 
 		err = mocks.controller.ScaleFromZero(mocks.canary)
@@ -257,7 +257,7 @@ func TestDaemonSetController_Scale(t *testing.T) {
 func TestDaemonSetController_Finalize(t *testing.T) {
 	dc := daemonsetConfigs{name: "podinfo", label: "name", labelValue: "podinfo"}
 	mocks := newDaemonSetFixture(dc)
-	err := mocks.controller.Initialize(mocks.canary)
+	_, err := mocks.controller.Initialize(mocks.canary)
 	require.NoError(t, err)
 
 	err = mocks.controller.Finalize(mocks.canary)
diff --git a/pkg/canary/daemonset_ready.go b/pkg/canary/daemonset_ready.go
index 6ce7a5745..f69714f63 100644
--- a/pkg/canary/daemonset_ready.go
+++ b/pkg/canary/daemonset_ready.go
@@ -29,18 +29,18 @@ import (
 
 // IsPrimaryReady checks the primary daemonset status and returns an error if
 // the daemonset is in the middle of a rolling update
-func (c *DaemonSetController) IsPrimaryReady(cd *flaggerv1.Canary) error {
+func (c *DaemonSetController) IsPrimaryReady(cd *flaggerv1.Canary) (bool, error) {
 	primaryName := fmt.Sprintf("%s-primary", cd.Spec.TargetRef.Name)
 	primary, err := c.kubeClient.AppsV1().DaemonSets(cd.Namespace).Get(context.TODO(), primaryName, metav1.GetOptions{})
 	if err != nil {
-		return fmt.Errorf("daemonset %s.%s get query error: %w", primaryName, cd.Namespace, err)
+		return true, fmt.Errorf("daemonset %s.%s get query error: %w", primaryName, cd.Namespace, err)
 	}
 
-	_, err = c.isDaemonSetReady(cd, primary, cd.GetAnalysisPrimaryReadyThreshold())
+	retriable, err := c.isDaemonSetReady(cd, primary, cd.GetAnalysisPrimaryReadyThreshold())
 	if err != nil {
-		return fmt.Errorf("primary daemonset %s.%s not ready: %w", primaryName, cd.Namespace, err)
+		return retriable, fmt.Errorf("primary daemonset %s.%s not ready: %w", primaryName, cd.Namespace, err)
 	}
-	return nil
+	return true, nil
 }
 
 // IsCanaryReady checks the primary daemonset and returns an error if
diff --git a/pkg/canary/daemonset_ready_test.go b/pkg/canary/daemonset_ready_test.go
index 755193fe1..c3acc9744 100644
--- a/pkg/canary/daemonset_ready_test.go
+++ b/pkg/canary/daemonset_ready_test.go
@@ -30,10 +30,10 @@ import (
 func TestDaemonSetController_IsReady(t *testing.T) {
 	dc := daemonsetConfigs{name: "podinfo", label: "name", labelValue: "podinfo"}
 	mocks := newDaemonSetFixture(dc)
-	err := mocks.controller.Initialize(mocks.canary)
+	_, err := mocks.controller.Initialize(mocks.canary)
 	require.NoError(t, err)
 
-	err = mocks.controller.IsPrimaryReady(mocks.canary)
+	_, err = mocks.controller.IsPrimaryReady(mocks.canary)
 	require.NoError(t, err)
 
 	_, err = mocks.controller.IsCanaryReady(mocks.canary)
diff --git a/pkg/canary/daemonset_status_test.go b/pkg/canary/daemonset_status_test.go
index 14d502f27..52193ed21 100644
--- a/pkg/canary/daemonset_status_test.go
+++ b/pkg/canary/daemonset_status_test.go
@@ -30,7 +30,7 @@ import (
 func TestDaemonSetController_SyncStatus(t *testing.T) {
 	dc := daemonsetConfigs{name: "podinfo", label: "name", labelValue: "podinfo"}
 	mocks := newDaemonSetFixture(dc)
-	err := mocks.controller.Initialize(mocks.canary)
+	_, err := mocks.controller.Initialize(mocks.canary)
 	require.NoError(t, err)
 
 	status := flaggerv1.CanaryStatus{
@@ -55,7 +55,7 @@ func TestDaemonSetController_SyncStatus(t *testing.T) {
 func TestDaemonSetController_SetFailedChecks(t *testing.T) {
 	dc := daemonsetConfigs{name: "podinfo", label: "name", labelValue: "podinfo"}
 	mocks := newDaemonSetFixture(dc)
-	err := mocks.controller.Initialize(mocks.canary)
+	_, err := mocks.controller.Initialize(mocks.canary)
 	require.NoError(t, err)
 
 	err = mocks.controller.SetStatusFailedChecks(mocks.canary, 1)
@@ -69,7 +69,7 @@ func TestDaemonSetController_SetFailedChecks(t *testing.T) {
 func TestDaemonSetController_SetState(t *testing.T) {
 	dc := daemonsetConfigs{name: "podinfo", label: "name", labelValue: "podinfo"}
 	mocks := newDaemonSetFixture(dc)
-	err := mocks.controller.Initialize(mocks.canary)
+	_, err := mocks.controller.Initialize(mocks.canary)
 	require.NoError(t, err)
 
 	err = mocks.controller.SetStatusPhase(mocks.canary, flaggerv1.CanaryPhaseProgressing)
diff --git a/pkg/canary/deployment_controller.go b/pkg/canary/deployment_controller.go
index 3d605bad1..9c1d5f34d 100644
--- a/pkg/canary/deployment_controller.go
+++ b/pkg/canary/deployment_controller.go
@@ -44,20 +44,20 @@ type DeploymentController struct {
 }
 
 // Initialize creates the primary deployment if it does not exist.
-func (c *DeploymentController) Initialize(cd *flaggerv1.Canary) (err error) {
+func (c *DeploymentController) Initialize(cd *flaggerv1.Canary) (bool, error) {
 	if err := c.createPrimaryDeployment(cd, c.includeLabelPrefix); err != nil {
-		return fmt.Errorf("createPrimaryDeployment failed: %w", err)
+		return true, fmt.Errorf("createPrimaryDeployment failed: %w", err)
 	}
 
 	if cd.Status.Phase == "" || cd.Status.Phase == flaggerv1.CanaryPhaseInitializing {
 		if !cd.SkipAnalysis() {
-			if err := c.IsPrimaryReady(cd); err != nil {
-				return fmt.Errorf("%w", err)
+			if retriable, err := c.IsPrimaryReady(cd); err != nil {
+				return retriable, fmt.Errorf("%w", err)
 			}
 		}
 	}
 
-	return nil
+	return true, nil
 }
 
 // Promote copies the pod spec, secrets and config maps from canary to primary
diff --git a/pkg/canary/deployment_fixture_test.go b/pkg/canary/deployment_fixture_test.go
index ecdf7bf29..0ebf07eea 100644
--- a/pkg/canary/deployment_fixture_test.go
+++ b/pkg/canary/deployment_fixture_test.go
@@ -55,7 +55,7 @@ type deploymentConfigs struct {
 }
 
 func (d deploymentControllerFixture) initializeCanary(t *testing.T) {
-	err := d.controller.Initialize(d.canary)
+	_, err := d.controller.Initialize(d.canary)
 	require.Error(t, err) // not ready yet
 
 	primaryName := fmt.Sprintf("%s-primary", d.canary.Spec.TargetRef.Name)
@@ -73,7 +73,8 @@ func (d deploymentControllerFixture) initializeCanary(t *testing.T) {
 	_, err = d.controller.kubeClient.AppsV1().Deployments(d.canary.Namespace).Update(context.TODO(), p, metav1.UpdateOptions{})
 	require.NoError(t, err)
 
-	require.NoError(t, d.controller.Initialize(d.canary))
+	_, err = d.controller.Initialize(d.canary)
+	require.NoError(t, err)
 }
 
 func newDeploymentFixture(dc deploymentConfigs) deploymentControllerFixture {
diff --git a/pkg/canary/deployment_ready.go b/pkg/canary/deployment_ready.go
index 431aa1ce6..0d88055e9 100644
--- a/pkg/canary/deployment_ready.go
+++ b/pkg/canary/deployment_ready.go
@@ -30,23 +30,23 @@ import (
 // IsPrimaryReady checks the primary deployment status and returns an error if
 // the deployment is in the middle of a rolling update or if the pods are unhealthy
 // it will return a non retryable error if the rolling update is stuck
-func (c *DeploymentController) IsPrimaryReady(cd *flaggerv1.Canary) error {
+func (c *DeploymentController) IsPrimaryReady(cd *flaggerv1.Canary) (bool, error) {
 	primaryName := fmt.Sprintf("%s-primary", cd.Spec.TargetRef.Name)
 	primary, err := c.kubeClient.AppsV1().Deployments(cd.Namespace).Get(context.TODO(), primaryName, metav1.GetOptions{})
 	if err != nil {
-		return fmt.Errorf("deployment %s.%s get query error: %w", primaryName, cd.Namespace, err)
+		return true, fmt.Errorf("deployment %s.%s get query error: %w", primaryName, cd.Namespace, err)
 	}
 
-	_, err = c.isDeploymentReady(primary, cd.GetProgressDeadlineSeconds(), cd.GetAnalysisPrimaryReadyThreshold())
+	retriable, err := c.isDeploymentReady(primary, cd.GetProgressDeadlineSeconds(), cd.GetAnalysisPrimaryReadyThreshold())
 	if err != nil {
-		return fmt.Errorf("%s.%s not ready: %w", primaryName, cd.Namespace, err)
+		return retriable, fmt.Errorf("%s.%s not ready: %w", primaryName, cd.Namespace, err)
 	}
 
 	if primary.Spec.Replicas == int32p(0) {
-		return fmt.Errorf("halt %s.%s advancement: primary deployment is scaled to zero",
+		return false, fmt.Errorf("halt %s.%s advancement: primary deployment is scaled to zero",
 			cd.Name, cd.Namespace)
 	}
-	return nil
+	return true, nil
 }
 
 // IsCanaryReady checks the canary deployment status and returns an error if
diff --git a/pkg/canary/deployment_ready_test.go b/pkg/canary/deployment_ready_test.go
index 8719ee113..05c8867b9 100644
--- a/pkg/canary/deployment_ready_test.go
+++ b/pkg/canary/deployment_ready_test.go
@@ -32,7 +32,7 @@ func TestDeploymentController_IsReady(t *testing.T) {
 	mocks := newDeploymentFixture(dc)
 	mocks.controller.Initialize(mocks.canary)
 
-	err := mocks.controller.IsPrimaryReady(mocks.canary)
+	_, err := mocks.controller.IsPrimaryReady(mocks.canary)
 	require.Error(t, err)
 
 	_, err = mocks.controller.IsCanaryReady(mocks.canary)
diff --git a/pkg/canary/service_controller.go b/pkg/canary/service_controller.go
index cb8d559e0..97de616aa 100644
--- a/pkg/canary/service_controller.go
+++ b/pkg/canary/service_controller.go
@@ -66,25 +66,25 @@ func (c *ServiceController) GetMetadata(_ *flaggerv1.Canary) (string, string, ma
 }
 
 // Initialize creates or updates the primary and canary services to prepare for the canary release process targeted on the K8s service
-func (c *ServiceController) Initialize(cd *flaggerv1.Canary) (err error) {
+func (c *ServiceController) Initialize(cd *flaggerv1.Canary) (bool, error) {
 	targetName := cd.Spec.TargetRef.Name
 	primaryName := fmt.Sprintf("%s-primary", targetName)
 	canaryName := fmt.Sprintf("%s-canary", targetName)
 
 	svc, err := c.kubeClient.CoreV1().Services(cd.Namespace).Get(context.TODO(), targetName, metav1.GetOptions{})
 	if err != nil {
-		return fmt.Errorf("service %s.%s get query error: %w", primaryName, cd.Namespace, err)
+		return true, fmt.Errorf("service %s.%s get query error: %w", primaryName, cd.Namespace, err)
 	}
 
 	if err = c.reconcileCanaryService(cd, canaryName, svc); err != nil {
-		return fmt.Errorf("reconcileCanaryService failed: %w", err)
+		return true, fmt.Errorf("reconcileCanaryService failed: %w", err)
 	}
 
 	if err = c.reconcilePrimaryService(cd, primaryName, svc); err != nil {
-		return fmt.Errorf("reconcilePrimaryService failed: %w", err)
+		return true, fmt.Errorf("reconcilePrimaryService failed: %w", err)
 	}
 
-	return nil
+	return true, nil
 }
 
 func (c *ServiceController) reconcileCanaryService(canary *flaggerv1.Canary, name string, src *corev1.Service) error {
@@ -249,8 +249,8 @@ func (c *ServiceController) HaveDependenciesChanged(_ *flaggerv1.Canary) (bool,
 	return false, nil
 }
 
-func (c *ServiceController) IsPrimaryReady(_ *flaggerv1.Canary) error {
-	return nil
+func (c *ServiceController) IsPrimaryReady(_ *flaggerv1.Canary) (bool, error) {
+	return true, nil
 }
 
 func (c *ServiceController) IsCanaryReady(_ *flaggerv1.Canary) (bool, error) {
diff --git a/pkg/controller/scheduler.go b/pkg/controller/scheduler.go
index 6168b24a6..6a9a2664a 100644
--- a/pkg/controller/scheduler.go
+++ b/pkg/controller/scheduler.go
@@ -221,9 +221,12 @@ func (c *Controller) advanceCanary(name string, namespace string) {
 	}
 
 	// create primary workload
-	err = canaryController.Initialize(cd)
+	retriable, err := canaryController.Initialize(cd)
 	if err != nil {
 		c.recordEventWarningf(cd, "%v", err)
+		if !retriable {
+			c.rollback(cd, canaryController, meshRouter, scalerReconciler)
+		}
 		return
 	}
 
@@ -289,8 +292,12 @@ func (c *Controller) advanceCanary(name string, namespace string) {
 
 	// check primary status
 	if !cd.SkipAnalysis() {
-		if err := canaryController.IsPrimaryReady(cd); err != nil {
+		retriable, err := canaryController.IsPrimaryReady(cd)
+		if err != nil {
 			c.recordEventWarningf(cd, "%v", err)
+			if !retriable {
+				c.rollback(cd, canaryController, meshRouter, scalerReconciler)
+			}
 			return
 		}
 	}
@@ -336,10 +343,12 @@ func (c *Controller) advanceCanary(name string, namespace string) {
 	}
 
 	// check canary status
-	var retriable = true
 	retriable, err = canaryController.IsCanaryReady(cd)
-	if err != nil && retriable {
+	if err != nil {
 		c.recordEventWarningf(cd, "%v", err)
+		if !retriable {
+			c.rollback(cd, canaryController, meshRouter, scalerReconciler)
+		}
 		return
 	}