diff --git a/otoroshi/app/utils/letsencrypt.scala b/otoroshi/app/utils/letsencrypt.scala
index 6e2547b2f..c96fd3be2 100644
--- a/otoroshi/app/utils/letsencrypt.scala
+++ b/otoroshi/app/utils/letsencrypt.scala
@@ -12,6 +12,7 @@ import otoroshi.events.{Alerts, CertRenewalAlert}
 import otoroshi.ssl.DynamicSSLEngineProvider.base64Decode
 import otoroshi.ssl.{Cert, PemHeaders}
 import otoroshi.utils.RegexPool
+import otoroshi.utils.syntax.implicits.BetterFiniteDuration
 import play.api.Logger
 import play.api.libs.json._
 
@@ -309,8 +310,11 @@ object LetsEncryptHelper {
             s"${env.storageRoot}:letsencrypt:challenges:$domain:${challenge.getToken}",
             ByteString(challenge.getAuthorization),
             Some(10.minutes.toMillis)
-          )
-          authorizeOrder(domain, authorization.getStatus, challenge)
+          ).flatMap { _ =>
+            3.seconds.timeout.flatMap { _ =>
+              authorizeOrder(domain, authorization.getStatus, challenge)
+            }
+          }
       }
       .toMat(Sink.seq)(Keep.right)
       .run()
@@ -333,7 +337,7 @@ object LetsEncryptHelper {
       } else {
         challenge.trigger()
         Source
-          .tick(1.seconds, 3.seconds, ())
+          .tick(3.seconds, 3.seconds, ())
           .mapAsync(1) { _ =>
             Future {
               challenge.update()
@@ -364,7 +368,7 @@ object LetsEncryptHelper {
       order.execute(csr)
     }(blockingEc).flatMap { _ =>
       Source
-        .tick(1.seconds, 5.seconds, ())
+        .tick(3.seconds, 5.seconds, ())
         .mapAsync(1) { _ =>
           Future {
             order.update()
diff --git a/otoroshi/app/utils/syntax.scala b/otoroshi/app/utils/syntax.scala
index 129da2f39..5245b865c 100644
--- a/otoroshi/app/utils/syntax.scala
+++ b/otoroshi/app/utils/syntax.scala
@@ -8,6 +8,7 @@ import com.auth0.jwt.interfaces.DecodedJWT
 import com.github.blemale.scaffeine.Cache
 import com.typesafe.config.{ConfigFactory, ConfigRenderOptions}
 import org.apache.commons.codec.binary.{Base64, Hex}
+import otoroshi.env.Env
 import otoroshi.models.WSProxyServerJson
 import otoroshi.next.utils.JsonHelpers
 import otoroshi.ssl.DynamicSSLEngineProvider
@@ -28,7 +29,7 @@ import java.util.concurrent.TimeUnit
 import java.util.concurrent.atomic.{AtomicInteger, AtomicLong, AtomicReference}
 import scala.collection.TraversableOnce
 import scala.collection.concurrent.TrieMap
-import scala.concurrent.duration.Duration
+import scala.concurrent.duration.{Duration, FiniteDuration}
 import scala.concurrent.{Await, ExecutionContext, Future, Promise}
 import scala.reflect.ClassTag
 import scala.util.control.{NoStackTrace, NonFatal}
@@ -595,6 +596,16 @@ object implicits {
       }
     }
   }
+  implicit class BetterFiniteDuration(val duration: FiniteDuration)                       extends AnyVal {
+    def timeout(implicit env: Env, ec: ExecutionContext): Future[Unit] = await(env, ec)
+    def await(implicit env: Env, ec: ExecutionContext): Future[Unit] = {
+      val promise = Promise.apply[Unit]()
+      env.otoroshiScheduler.scheduleOnce(duration) {
+        promise.trySuccess(())
+      }
+      promise.future
+    }
+  }
   implicit class BetterDuration(val duration: Duration)                       extends AnyVal {
     final def toHumanReadable: String = {
       val units       = Seq(