diff --git a/integration/run/run_test.go b/integration/run/run_test.go
index c52646481..e660d2946 100644
--- a/integration/run/run_test.go
+++ b/integration/run/run_test.go
@@ -7,7 +7,6 @@ import (
 	"strings"
 	"testing"
 
-	"github.com/acorn-io/baaah/pkg/apply"
 	"github.com/acorn-io/baaah/pkg/restconfig"
 	"github.com/acorn-io/baaah/pkg/router"
 	"github.com/acorn-io/runtime/integration/helper"
@@ -1194,7 +1193,7 @@ func TestJobDelete(t *testing.T) {
 	}
 
 	app = helper.WaitForObject(t, helper.Watcher(t, c), new(apiv1.AppList), app, func(app *apiv1.App) bool {
-		return len(app.Finalizers) > 0 && app.Annotations[apply.AnnotationPrune] == "false"
+		return len(app.Finalizers) > 0
 	})
 
 	app, err = c.AppDelete(ctx, app.Name)
diff --git a/integration/services/services_test.go b/integration/services/services_test.go
index 5355e457c..6ec8f95ab 100644
--- a/integration/services/services_test.go
+++ b/integration/services/services_test.go
@@ -67,6 +67,11 @@ func TestServiceIgnoreCleanup(t *testing.T) {
 		t.Fatal(err)
 	}
 
+	// Delete the service.
+	if _, err := c.AppDelete(ctx, "myapp.myservice"); err != nil {
+		t.Fatal(err)
+	}
+
 	// This app's service has a delete event job that will fail to run.
 	// Make sure it still shows up in the app list.
 	list, err := c.AppList(ctx)
diff --git a/pkg/controller/appdefinition/acorn.go b/pkg/controller/appdefinition/acorn.go
index 83c008f00..8d7574508 100644
--- a/pkg/controller/appdefinition/acorn.go
+++ b/pkg/controller/appdefinition/acorn.go
@@ -10,24 +10,39 @@ import (
 	"github.com/acorn-io/baaah/pkg/typed"
 	v1 "github.com/acorn-io/runtime/pkg/apis/internal.acorn.io/v1"
 	"github.com/acorn-io/runtime/pkg/autoupgrade"
+	"github.com/acorn-io/runtime/pkg/controller/jobs"
 	"github.com/acorn-io/runtime/pkg/images"
 	"github.com/acorn-io/runtime/pkg/labels"
 	"github.com/acorn-io/runtime/pkg/ports"
 	"github.com/acorn-io/runtime/pkg/publicname"
 	"github.com/google/go-containerregistry/pkg/name"
+	"golang.org/x/exp/slices"
+	apierrors "k8s.io/apimachinery/pkg/api/errors"
 	metav1 "k8s.io/apimachinery/pkg/apis/meta/v1"
 )
 
-func addAcorns(req router.Request, appInstance *v1.AppInstance, tag name.Reference, pullSecrets *PullSecrets, resp router.Response) {
+func addAcorns(req router.Request, appInstance *v1.AppInstance, tag name.Reference, pullSecrets *PullSecrets, resp router.Response) error {
 	for _, acorn := range toAcorns(appInstance, tag, pullSecrets) {
 		var devSession v1.DevSessionInstance
 		err := req.Get(&devSession, acorn.Namespace, acorn.Name)
 		if err == nil {
 			// Don't update app in dev mode
 			acorn.Annotations[apply.AnnotationUpdate] = "false"
+		} else if !apierrors.IsNotFound(err) {
+			return err
+		}
+		var existingApp v1.AppInstance
+		err = req.Get(&existingApp, acorn.Namespace, acorn.Name)
+		if err == nil {
+			if slices.Contains(existingApp.Finalizers, jobs.DestroyJobFinalizer) {
+				acorn.Annotations[apply.AnnotationPrune] = "false"
+			}
+		} else if !apierrors.IsNotFound(err) {
+			return err
 		}
 		resp.Objects(acorn)
 	}
+	return nil
 }
 
 func toAcorns(appInstance *v1.AppInstance, tag name.Reference, pullSecrets *PullSecrets) (result []*v1.AppInstance) {
diff --git a/pkg/controller/config/devconfig.go b/pkg/controller/config/devconfig.go
index f22e54b69..ea4f3f80d 100644
--- a/pkg/controller/config/devconfig.go
+++ b/pkg/controller/config/devconfig.go
@@ -20,6 +20,8 @@ func PurgeDevConfig(req router.Request, resp router.Response) error {
 		expiration, err := time.Parse(time.RFC3339, ttlString)
 		if err == nil {
 			if time.Now().Before(expiration) {
+				// Look 15 minutes later (stupid simple logic)
+				resp.RetryAfter(15 * time.Minute)
 				return nil
 			}
 			logrus.Infof("Time on dev config has expired [%s]", ttlString)
diff --git a/pkg/controller/jobs/finalize.go b/pkg/controller/jobs/finalize.go
index 5ecad1bb6..baac9ea59 100644
--- a/pkg/controller/jobs/finalize.go
+++ b/pkg/controller/jobs/finalize.go
@@ -4,7 +4,6 @@ import (
 	"sort"
 	"time"
 
-	"github.com/acorn-io/baaah/pkg/apply"
 	"github.com/acorn-io/baaah/pkg/router"
 	v1 "github.com/acorn-io/runtime/pkg/apis/internal.acorn.io/v1"
 	"github.com/acorn-io/runtime/pkg/labels"
@@ -89,16 +88,6 @@ func NeedsDestroyJobFinalization(next router.Handler) router.Handler {
 		}
 
 		if shouldFinalize(app) {
-			if app.Annotations[apply.AnnotationPrune] != "false" {
-				if app.Annotations == nil {
-					app.Annotations = map[string]string{}
-				}
-				app.Annotations[apply.AnnotationPrune] = "false"
-				if err := req.Client.Update(req.Ctx, app); err != nil {
-					return err
-				}
-			}
-
 			return next.Handle(req, resp)
 		}