diff --git a/pkg/controller/acmechallenges/controller.go b/pkg/controller/acmechallenges/controller.go
index fcb3348f6..af1c3bd70 100644
--- a/pkg/controller/acmechallenges/controller.go
+++ b/pkg/controller/acmechallenges/controller.go
@@ -70,8 +70,7 @@ func New(ctx *controllerpkg.Context) *Controller {
 	ctrl := &Controller{Context: *ctx}
 	ctrl.syncHandler = ctrl.processNextWorkItem
 
-	// exponentially back-off self checks, with a base of 2s and max wait of 20s
-	ctrl.queue = workqueue.NewNamedRateLimitingQueue(controllerpkg.DefaultItemBasedRateLimiter(), "challenges")
+	ctrl.queue = workqueue.NewNamedRateLimitingQueue(workqueue.NewItemExponentialFailureRateLimiter(time.Second*5, time.Minute*30), "challenges")
 
 	challengeInformer := ctrl.SharedInformerFactory.Certmanager().V1alpha1().Challenges()
 	challengeInformer.Informer().AddEventHandler(&controllerpkg.QueuingEventHandler{Queue: ctrl.queue})
diff --git a/pkg/controller/acmechallenges/sync.go b/pkg/controller/acmechallenges/sync.go
index ee8166244..3b78a4e33 100644
--- a/pkg/controller/acmechallenges/sync.go
+++ b/pkg/controller/acmechallenges/sync.go
@@ -161,8 +161,8 @@ func (c *Controller) Sync(ctx context.Context, ch *cmapi.Challenge) (err error)
 			return err
 		}
 
-		// retry after 5s
-		c.queue.AddAfter(key, time.Second*5)
+		// retry after 10s
+		c.queue.AddAfter(key, time.Second*10)
 
 		return nil
 	}
diff --git a/pkg/controller/acmeorders/controller.go b/pkg/controller/acmeorders/controller.go
index 620ebb13d..81c2871a8 100644
--- a/pkg/controller/acmeorders/controller.go
+++ b/pkg/controller/acmeorders/controller.go
@@ -65,7 +65,7 @@ func New(ctx *controllerpkg.Context) *Controller {
 	ctrl := &Controller{Context: *ctx}
 	ctrl.syncHandler = ctrl.processNextWorkItem
 
-	ctrl.queue = workqueue.NewNamedRateLimitingQueue(controllerpkg.DefaultItemBasedRateLimiter(), "orders")
+	ctrl.queue = workqueue.NewNamedRateLimitingQueue(workqueue.NewItemExponentialFailureRateLimiter(time.Second*5, time.Minute*30), "orders")
 
 	orderInformer := ctrl.SharedInformerFactory.Certmanager().V1alpha1().Orders()
 	orderInformer.Informer().AddEventHandler(&controllerpkg.QueuingEventHandler{Queue: ctrl.queue})
diff --git a/pkg/issuer/acme/issue.go b/pkg/issuer/acme/issue.go
index 5784a6c83..12e19a880 100644
--- a/pkg/issuer/acme/issue.go
+++ b/pkg/issuer/acme/issue.go
@@ -42,7 +42,7 @@ import (
 )
 
 const (
-	createOrderWaitDuration = time.Minute * 5
+	createOrderWaitDuration = time.Hour * 1
 )
 
 var (
@@ -140,6 +140,7 @@ func (a *Acme) Issue(ctx context.Context, crt *v1alpha1.Certificate) (*issuer.Is
 		if crt.Status.LastFailureTime == nil {
 			nowTime := metav1.NewTime(a.clock.Now())
 			crt.Status.LastFailureTime = &nowTime
+			a.Recorder.Eventf(crt, corev1.EventTypeWarning, "FailedOrder", "Order %q failed. Waiting %s before retrying issuance.", existingOrder.Name, createOrderWaitDuration)
 		}
 
 		if time.Now().Sub(crt.Status.LastFailureTime.Time) < createOrderWaitDuration {