reconciler: fix deletion wait and updater retry logic

pkg/reconciler/internal/updater/updater.go

@@ -84,41 +84,40 @@ func (u *Updater) Apply(ctx context.Context, obj *unstructured.Unstructured) err
 
 	backoff := retry.DefaultRetry
 
+	st := statusFor(obj)
+	needsStatusUpdate := false
+	for _, f := range u.updateStatusFuncs {
+		needsStatusUpdate = f(st) || needsStatusUpdate
+	}
+
 	// Always update the status first. During uninstall, if
 	// we remove the finalizer, updating the status will fail
 	// because the object and its status will be garbage-collected.
-	if err := retryOnRetryableUpdateError(backoff, func() error {
-		st := statusFor(obj)
-		needsStatusUpdate := false
-		for _, f := range u.updateStatusFuncs {
-			needsStatusUpdate = f(st) || needsStatusUpdate
+	if needsStatusUpdate {
+		uSt, err := runtime.DefaultUnstructuredConverter.ToUnstructured(st)
+		if err != nil {
+			return err
 		}
-		if needsStatusUpdate {
-			uSt, err := runtime.DefaultUnstructuredConverter.ToUnstructured(st)
-			if err != nil {
-				return err
-			}
-			obj.Object["status"] = uSt
+		obj.Object["status"] = uSt
+
+		if err := retryOnRetryableUpdateError(backoff, func() error {
 			return u.client.Status().Update(ctx, obj)
+		}); err != nil {
+			return err
 		}
-		return nil
-	}); err != nil {
-		return err
 	}
 
-	if err := retryOnRetryableUpdateError(backoff, func() error {
-		needsUpdate := false
-		for _, f := range u.updateFuncs {
-			needsUpdate = f(obj) || needsUpdate
-		}
-		if needsUpdate {
+	needsUpdate := false
+	for _, f := range u.updateFuncs {
+		needsUpdate = f(obj) || needsUpdate
+	}
+	if needsUpdate {
+		if err := retryOnRetryableUpdateError(backoff, func() error {
 			return u.client.Update(ctx, obj)
+		}); err != nil {
+			return err
 		}
-		return nil
-	}); err != nil {
-		return err
 	}
-
 	return nil
 }
 

pkg/reconciler/internal/updater/updater_test.go

@@ -18,16 +18,19 @@ package updater
 
 import (
 	"context"
+	"errors"
 
 	. "github.com/onsi/ginkgo/v2"
 	. "github.com/onsi/gomega"
+
 	"helm.sh/helm/v3/pkg/release"
 	corev1 "k8s.io/api/core/v1"
 	apierrors "k8s.io/apimachinery/pkg/api/errors"
 	"k8s.io/apimachinery/pkg/apis/meta/v1/unstructured"
 	"k8s.io/apimachinery/pkg/types"
 	"sigs.k8s.io/controller-runtime/pkg/client"
 	"sigs.k8s.io/controller-runtime/pkg/client/fake"
+	"sigs.k8s.io/controller-runtime/pkg/client/interceptor"
 
 	"github.com/operator-framework/helm-operator-plugins/pkg/reconciler/internal/conditions"
 )
@@ -36,14 +39,15 @@ const testFinalizer = "testFinalizer"
 
 var _ = Describe("Updater", func() {
 	var (
-		client client.Client
-		u      Updater
-		obj    *unstructured.Unstructured
+		cl               client.Client
+		u                Updater
+		obj              *unstructured.Unstructured
+		interceptorFuncs interceptor.Funcs
 	)
 
-	BeforeEach(func() {
-		client = fake.NewClientBuilder().Build()
-		u = New(client)
+	JustBeforeEach(func() {
+		cl = fake.NewClientBuilder().WithInterceptorFuncs(interceptorFuncs).Build()
+		u = New(cl)
 		obj = &unstructured.Unstructured{Object: map[string]interface{}{
 			"apiVersion": "apps/v1",
 			"kind":       "Deployment",
@@ -53,12 +57,12 @@ var _ = Describe("Updater", func() {
 			},
 			"spec": map[string]interface{}{},
 		}}
-		Expect(client.Create(context.TODO(), obj)).To(Succeed())
+		Expect(cl.Create(context.TODO(), obj)).To(Succeed())
 	})
 
 	When("the object does not exist", func() {
 		It("should fail", func() {
-			Expect(client.Delete(context.TODO(), obj)).To(Succeed())
+			Expect(cl.Delete(context.TODO(), obj)).To(Succeed())
 			u.Update(func(u *unstructured.Unstructured) bool {
 				u.SetAnnotations(map[string]string{"foo": "bar"})
 				return true
@@ -70,6 +74,18 @@ var _ = Describe("Updater", func() {
 	})
 
 	When("an update is a change", func() {
+		var updateCallCount int
+
+		BeforeEach(func() {
+			// On the first update of (status) subresource, return an error. After that do what is expected.
+			interceptorFuncs.SubResourceUpdate = func(ctx context.Context, interceptorClient client.Client, subResourceName string, obj client.Object, opts ...client.SubResourceUpdateOption) error {
+				updateCallCount++
+				if updateCallCount == 1 {
+					return errors.New("transient error")
+				}
+				return interceptorClient.SubResource(subResourceName).Update(ctx, obj, opts...)
+			}
+		})
 		It("should apply an update function", func() {
 			u.Update(func(u *unstructured.Unstructured) bool {
 				u.SetAnnotations(map[string]string{"foo": "bar"})
@@ -78,7 +94,7 @@ var _ = Describe("Updater", func() {
 			resourceVersion := obj.GetResourceVersion()
 
 			Expect(u.Apply(context.TODO(), obj)).To(Succeed())
-			Expect(client.Get(context.TODO(), types.NamespacedName{Namespace: "testNamespace", Name: "testDeployment"}, obj)).To(Succeed())
+			Expect(cl.Get(context.TODO(), types.NamespacedName{Namespace: "testNamespace", Name: "testDeployment"}, obj)).To(Succeed())
 			Expect(obj.GetAnnotations()["foo"]).To(Equal("bar"))
 			Expect(obj.GetResourceVersion()).NotTo(Equal(resourceVersion))
 		})
@@ -88,7 +104,7 @@ var _ = Describe("Updater", func() {
 			resourceVersion := obj.GetResourceVersion()
 
 			Expect(u.Apply(context.TODO(), obj)).To(Succeed())
-			Expect(client.Get(context.TODO(), types.NamespacedName{Namespace: "testNamespace", Name: "testDeployment"}, obj)).To(Succeed())
+			Expect(cl.Get(context.TODO(), types.NamespacedName{Namespace: "testNamespace", Name: "testDeployment"}, obj)).To(Succeed())
 			Expect((obj.Object["status"].(map[string]interface{}))["conditions"]).To(HaveLen(1))
 			Expect(obj.GetResourceVersion()).NotTo(Equal(resourceVersion))
 		})

pkg/reconciler/internal/values/values.go

@@ -20,6 +20,7 @@ import (
 	"context"
 	"fmt"
 	"os"
+	"time"
 
 	"helm.sh/helm/v3/pkg/chartutil"
 	"helm.sh/helm/v3/pkg/strvals"
@@ -28,6 +29,8 @@ import (
 	"github.com/operator-framework/helm-operator-plugins/pkg/values"
 )
 
+var DefaultWaitForDeletionTimeout = 30 * time.Second
+
 var DefaultMaxReleaseHistory = 10
 
 var DefaultMapper = values.MapperFunc(func(v chartutil.Values) chartutil.Values { return v })

pkg/reconciler/reconciler.go

@@ -25,7 +25,6 @@ import (
 	"time"
 
 	"github.com/go-logr/logr"
-	sdkhandler "github.com/operator-framework/operator-lib/handler"
 	errs "github.com/pkg/errors"
 	"helm.sh/helm/v3/pkg/action"
 	"helm.sh/helm/v3/pkg/chart"
@@ -46,6 +45,8 @@ import (
 	"sigs.k8s.io/controller-runtime/pkg/predicate"
 	"sigs.k8s.io/controller-runtime/pkg/source"
 
+	sdkhandler "github.com/operator-framework/operator-lib/handler"
+
 	"github.com/operator-framework/helm-operator-plugins/internal/sdk/controllerutil"
 	"github.com/operator-framework/helm-operator-plugins/pkg/annotation"
 	helmclient "github.com/operator-framework/helm-operator-plugins/pkg/client"
@@ -78,6 +79,7 @@ type Reconciler struct {
 	skipDependentWatches             bool
 	maxConcurrentReconciles          int
 	reconcilePeriod                  time.Duration
+	waitForDeletionTimeout           time.Duration
 	maxReleaseHistory                *int
 	skipPrimaryGVKSchemeRegistration bool
 	controllerSetupFuncs             []ControllerSetupFunc
@@ -332,6 +334,20 @@ func WithMaxConcurrentReconciles(max int) Option {
 	}
 }
 
+// WithWaitForDeletionTimeout is an Option that configures how long to wait for the client to
+// report that the primary resource has been deleted. If the primary resource is not deleted
+// within this time, the reconciler will return an error and retry reconciliation. By default,
+// the reconciler will wait for 30s. This function requires positive values.
+func WithWaitForDeletionTimeout(timeout time.Duration) Option {
+	return func(r *Reconciler) error {
+		if timeout <= 0 {
+			return errors.New("wait for deletion timeout must be a positive value")
+		}
+		r.waitForDeletionTimeout = timeout
+		return nil
+	}
+}
+
 // WithReconcilePeriod is an Option that configures the reconcile period of the
 // controller. This will cause the controller to reconcile CRs at least once
 // every period. By default, the reconcile period is set to 0, which means no
@@ -727,13 +743,15 @@ func (r *Reconciler) handleDeletion(ctx context.Context, actionClient helmclient
 	}
 
 	// Since the client is hitting a cache, waiting for the
-	// deletion here will guarantee that the next reconciliation
+	// deletion here will help ensure that the next reconciliation
 	// will see that the CR has been deleted and that there's
 	// nothing left to do.
-	if err := controllerutil.WaitForDeletion(ctx, r.client, obj); err != nil {
-		return err
-	}
-	return nil
+	//
+	// If the CR is not deleted within the timeout, the next reconciliation
+	// will attempt to uninstall the release again.
+	timeoutCtx, timeoutCancel := context.WithTimeout(ctx, r.waitForDeletionTimeout)
+	defer timeoutCancel()
+	return controllerutil.WaitForDeletion(timeoutCtx, r.client, obj)
 }
 
 func (r *Reconciler) getReleaseState(client helmclient.ActionInterface, obj metav1.Object, vals map[string]interface{}) (*release.Release, helmReleaseState, error) {
@@ -939,6 +957,10 @@ func (r *Reconciler) addDefaults(mgr ctrl.Manager, controllerName string) error
 		r.valueMapper = internalvalues.DefaultMapper
 	}
 
+	if r.waitForDeletionTimeout == 0 {
+		r.waitForDeletionTimeout = internalvalues.DefaultWaitForDeletionTimeout
+	}
+
 	if r.maxReleaseHistory == nil {
 		r.maxReleaseHistory = &internalvalues.DefaultMaxReleaseHistory
 	}

pkg/reconciler/reconciler_test.go

@@ -24,11 +24,11 @@ import (
 	"strconv"
 	"time"
 
-	"github.com/go-logr/logr"
 	. "github.com/onsi/ginkgo/v2"
 	. "github.com/onsi/gomega"
 	. "github.com/onsi/gomega/gstruct"
-	sdkhandler "github.com/operator-framework/operator-lib/handler"
+
+	"github.com/go-logr/logr"
 	"helm.sh/helm/v3/pkg/action"
 	"helm.sh/helm/v3/pkg/chart"
 	"helm.sh/helm/v3/pkg/chartutil"
@@ -46,6 +46,7 @@ import (
 	"k8s.io/client-go/tools/record"
 	"sigs.k8s.io/controller-runtime/pkg/client"
 	"sigs.k8s.io/controller-runtime/pkg/client/fake"
+	"sigs.k8s.io/controller-runtime/pkg/client/interceptor"
 	"sigs.k8s.io/controller-runtime/pkg/event"
 	"sigs.k8s.io/controller-runtime/pkg/log/zap"
 	"sigs.k8s.io/controller-runtime/pkg/manager"
@@ -54,6 +55,8 @@ import (
 	"sigs.k8s.io/controller-runtime/pkg/source"
 	"sigs.k8s.io/yaml"
 
+	sdkhandler "github.com/operator-framework/operator-lib/handler"
+
 	"github.com/operator-framework/helm-operator-plugins/internal/sdk/controllerutil"
 	"github.com/operator-framework/helm-operator-plugins/pkg/annotation"
 	helmclient "github.com/operator-framework/helm-operator-plugins/pkg/client"
@@ -205,6 +208,18 @@ var _ = Describe("Reconciler", func() {
 				Expect(WithMaxConcurrentReconciles(-1)(r)).NotTo(Succeed())
 			})
 		})
+		_ = Describe("WithWaitForDeletionTimeout", func() {
+			It("should set the reconciler wait for deletion timeout", func() {
+				Expect(WithWaitForDeletionTimeout(time.Second)(r)).To(Succeed())
+				Expect(r.waitForDeletionTimeout).To(Equal(time.Second))
+			})
+			It("should fail if value is zero", func() {
+				Expect(WithWaitForDeletionTimeout(0)(r)).NotTo(Succeed())
+			})
+			It("should fail if value is negative", func() {
+				Expect(WithWaitForDeletionTimeout(-time.Second)(r)).NotTo(Succeed())
+			})
+		})
 		_ = Describe("WithReconcilePeriod", func() {
 			It("should set the reconciler reconcile period", func() {
 				Expect(WithReconcilePeriod(0)(r)).To(Succeed())
@@ -686,6 +701,55 @@ var _ = Describe("Reconciler", func() {
 							})
 						})
 					})
+					When("cache contains stale CR that has actually been deleted", func() {
+						// This test simulates what we expect to happen when we time out waiting for a CR that we
+						// deleted to be removed from the cache.
+						It("ignores not found errors and returns successfully", func() {
+							By("deleting the CR and then setting a finalizer on the stale CR", func() {
+								// We _actually_ remove the CR from the API server, but we'll make a fake client
+								// that returns the stale CR.
+								Expect(mgr.GetClient().Delete(ctx, obj)).To(Succeed())
+								Eventually(func() error {
+									return mgr.GetAPIReader().Get(ctx, objKey, obj)
+								}).Should(WithTransform(apierrors.IsNotFound, BeTrue()))
+
+								// We set the finalizer on the stale CR to simulate the typical state of the CR from a
+								// prior reconcile run that timed out waiting for the CR to be removed from the cache.
+								obj.SetFinalizers([]string{uninstallFinalizer})
+							})
+
+							By("configuring a client that returns the stale CR", func() {
+								// Make a client that returns the stale CR, but sends writes to the real client.
+								cl := fake.NewClientBuilder().WithObjects(obj).WithInterceptorFuncs(interceptor.Funcs{
+									Create: func(ctx context.Context, _ client.WithWatch, fakeObj client.Object, opts ...client.CreateOption) error {
+										return mgr.GetClient().Create(ctx, fakeObj, opts...)
+									},
+									Delete: func(ctx context.Context, _ client.WithWatch, fakeObj client.Object, opts ...client.DeleteOption) error {
+										return mgr.GetClient().Delete(ctx, fakeObj, opts...)
+									},
+									DeleteAllOf: func(ctx context.Context, _ client.WithWatch, fakeObj client.Object, opts ...client.DeleteAllOfOption) error {
+										return mgr.GetClient().DeleteAllOf(ctx, fakeObj, opts...)
+									},
+									Update: func(ctx context.Context, _ client.WithWatch, fakeObj client.Object, opts ...client.UpdateOption) error {
+										return mgr.GetClient().Update(ctx, fakeObj, opts...)
+									},
+									Patch: func(ctx context.Context, _ client.WithWatch, fakeObj client.Object, patch client.Patch, opts ...client.PatchOption) error {
+										return mgr.GetClient().Patch(ctx, fakeObj, patch, opts...)
+									},
+									SubResource: func(_ client.WithWatch, subresource string) client.SubResourceClient {
+										return mgr.GetClient().SubResource(subresource)
+									},
+								}).WithStatusSubresource(obj).Build()
+								r.client = cl
+							})
+
+							By("successfully ignoring not found errors and returning a nil error", func() {
+								res, err := r.Reconcile(ctx, req)
+								Expect(res).To(Equal(reconcile.Result{}))
+								Expect(err).ToNot(HaveOccurred())
+							})
+						})
+					})
 					When("CR is deleted, release is not present, but uninstall finalizer exists", func() {
 						It("removes the finalizer", func() {
 							By("adding the uninstall finalizer and deleting the CR", func() {