diff --git a/api/v1/installation_types.go b/api/v1/installation_types.go
index f5ae789d..7a66154f 100644
--- a/api/v1/installation_types.go
+++ b/api/v1/installation_types.go
@@ -11,8 +11,11 @@ import (
 )
 
 const (
-	Prefix          = "getporter.org/"
-	AnnotationRetry = Prefix + "retry"
+	Prefix                       = "getporter.org/"
+	AnnotationRetry              = Prefix + "retry"
+	PorterDeletePolicyAnnotation = "getporter.org/deletion-policy"
+	PorterDeletePolicyDelete     = "Delete"
+	PorterDeletePolicyOrphan     = "Orphan"
 )
 
 // We marshal installation spec to yaml when converting to a porter object
diff --git a/controllers/installation_controller.go b/controllers/installation_controller.go
index c1ed5025..98b8f768 100644
--- a/controllers/installation_controller.go
+++ b/controllers/installation_controller.go
@@ -157,6 +157,13 @@ func (r *InstallationReconciler) Reconcile(ctx context.Context, req ctrl.Request
 		return ctrl.Result{}, err
 	}
 
+	log.V(Log4Debug).Info("Reconciliation complete: A porter agent has been dispatched to apply changes to the installation.")
+	// NOTE:  If this is nil, it will use the default policy of Delete
+	err = r.applyDeletionPolicy(ctx, log, inst, inst.GetAnnotations()[v1.PorterDeletePolicyAnnotation])
+	if err != nil {
+		return ctrl.Result{}, err
+	}
+
 	log.V(Log4Debug).Info("Reconciliation complete: A porter agent has been dispatched to apply changes to the installation.")
 	if r.PorterGRPCClient != nil {
 		return r.CheckOrCreateInstallationOutputsCR(ctx, log, inst)
@@ -404,3 +411,27 @@ func (r *InstallationReconciler) retry(ctx context.Context, log logr.Logger, ins
 	log.V(Log4Debug).Info("Retried associated porter agent action", "name", "retry", action.Name, retry)
 	return nil
 }
+
+func (r *InstallationReconciler) applyDeletionPolicy(ctx context.Context, log logr.Logger, inst *v1.Installation, policy string) error {
+	log.V(Log5Trace).Info("updating deletion policy")
+	annotations := inst.GetAnnotations()
+	if len(annotations) < 1 {
+		annotations = map[string]string{}
+	}
+
+	if _, ok := annotations[v1.PorterDeletePolicyAnnotation]; !ok {
+		annotations[v1.PorterDeletePolicyAnnotation] = v1.PorterDeletePolicyDelete
+		inst.SetAnnotations(annotations)
+		return r.Update(ctx, inst)
+	}
+
+	if policy != v1.PorterDeletePolicyOrphan && policy != v1.PorterDeletePolicyDelete {
+		annotations[v1.PorterDeletePolicyAnnotation] = v1.PorterDeletePolicyDelete
+		inst.SetAnnotations(annotations)
+		return r.Update(ctx, inst)
+	}
+
+	annotations[v1.PorterDeletePolicyAnnotation] = policy
+	inst.SetAnnotations(annotations)
+	return r.Update(ctx, inst)
+}
diff --git a/controllers/installation_controller_test.go b/controllers/installation_controller_test.go
index 691f27b2..c443a566 100644
--- a/controllers/installation_controller_test.go
+++ b/controllers/installation_controller_test.go
@@ -523,3 +523,67 @@ func TestIsHandled(t *testing.T) {
 	_, _, err := r.isHandled(ctx, logr.Discard(), inst)
 	assert.Error(t, err)
 }
+
+func TestApplyDeletionPolicyWithNoAnnotation(t *testing.T) {
+	tests := map[string]struct {
+		wantPolicy string
+		policy     string
+	}{
+		"empty-string":  {policy: "", wantPolicy: v1.PorterDeletePolicyDelete},
+		"policy-orphan": {policy: v1.PorterDeletePolicyOrphan, wantPolicy: v1.PorterDeletePolicyOrphan},
+		"policy-delete": {policy: v1.PorterDeletePolicyDelete, wantPolicy: v1.PorterDeletePolicyDelete},
+	}
+	ctx := context.Background()
+	inst := &v1.Installation{
+		ObjectMeta: metav1.ObjectMeta{
+			Name:      "fake-install",
+			Namespace: "fake-ns",
+		},
+		Spec: v1.InstallationSpec{
+			Name:      "fake-install",
+			Namespace: "fake-ns",
+		},
+	}
+
+	scheme := runtime.NewScheme()
+	utilruntime.Must(v1.AddToScheme(scheme))
+	fakeClient := fake.NewClientBuilder().WithScheme(scheme).WithObjects(inst).WithStatusSubresource(inst).Build()
+	rc := &InstallationReconciler{
+		Client: fakeClient,
+	}
+	for name, test := range tests {
+		t.Run(name, func(t *testing.T) {
+			err := rc.applyDeletionPolicy(ctx, logr.Discard(), inst, test.policy)
+			assert.NoError(t, err)
+			assert.Equal(t, inst.GetAnnotations()[v1.PorterDeletePolicyAnnotation], test.wantPolicy)
+		})
+	}
+}
+
+func TestApplyDeletionPolicyWithAnnotation(t *testing.T) {
+	ctx := context.Background()
+	inst := &v1.Installation{
+		ObjectMeta: metav1.ObjectMeta{
+			Name:      "fake-install",
+			Namespace: "fake-ns",
+			Annotations: map[string]string{
+				v1.PorterDeletePolicyAnnotation: v1.PorterDeletePolicyDelete,
+			},
+		},
+		Spec: v1.InstallationSpec{
+			Name:      "fake-install",
+			Namespace: "fake-ns",
+		},
+	}
+
+	scheme := runtime.NewScheme()
+	utilruntime.Must(v1.AddToScheme(scheme))
+	fakeClient := fake.NewClientBuilder().WithScheme(scheme).WithObjects(inst).WithStatusSubresource(inst).Build()
+	rc := &InstallationReconciler{
+		Client: fakeClient,
+	}
+
+	err := rc.applyDeletionPolicy(ctx, logr.Discard(), inst, "")
+	assert.NoError(t, err)
+	assert.Equal(t, inst.GetAnnotations()[v1.PorterDeletePolicyAnnotation], v1.PorterDeletePolicyDelete)
+}