diff --git a/src/client/Client.js b/src/client/Client.js
index f3a6617d5..e285b9237 100644
--- a/src/client/Client.js
+++ b/src/client/Client.js
@@ -436,6 +436,9 @@ class Client extends BaseClient {
     if (!(options.disabledEvents instanceof Array)) {
       throw new TypeError('CLIENT_INVALID_OPTION', 'disabledEvents', 'an Array');
     }
+    if (typeof options.retryLimit !== 'number' || isNaN(options.retryLimit)) {
+      throw new TypeError('CLIENT_INVALID_OPTION', 'retryLimit', 'a number');
+    }
   }
 }
 
diff --git a/src/rest/RESTManager.js b/src/rest/RESTManager.js
index 3d42b0b0e..53a8047f5 100644
--- a/src/rest/RESTManager.js
+++ b/src/rest/RESTManager.js
@@ -41,6 +41,7 @@ class RESTManager {
         request: apiRequest,
         resolve,
         reject,
+        retries: 0,
       }).catch(reject);
     });
   }
diff --git a/src/rest/RequestHandler.js b/src/rest/RequestHandler.js
index c6ea73ba5..99595b4b1 100644
--- a/src/rest/RequestHandler.js
+++ b/src/rest/RequestHandler.js
@@ -150,13 +150,13 @@ class RequestHandler {
       await Util.delayFor(this.retryAfter);
       return this.run();
     } else if (res.status >= 500 && res.status < 600) {
-      // Retry once for possible serverside issues
-      if (item.retried) {
+      // Retry the specified number of times for possible serverside issues
+      if (item.retries === this.manager.client.options.retryLimit) {
         return reject(
           new HTTPError(res.statusText, res.constructor.name, res.status, item.request.method, request.route)
         );
       } else {
-        item.retried = true;
+        item.retries++;
         this.queue.unshift(item);
         return this.run();
       }
diff --git a/src/util/Constants.js b/src/util/Constants.js
index b2e02c3ab..c4ab29a93 100644
--- a/src/util/Constants.js
+++ b/src/util/Constants.js
@@ -23,6 +23,7 @@ const browser = exports.browser = typeof window !== 'undefined';
  * requests (higher values will reduce rate-limiting errors on bad connections)
  * @property {number} [restSweepInterval=60] How frequently to delete inactive request buckets, in seconds
  * (or 0 for never)
+ * @property {number} [retryLimit=1] How many times to retry on 5XX errors (Infinity for indefinite amount of retries)
  * @property {PresenceData} [presence] Presence data to use upon login
  * @property {WSEventType[]} [disabledEvents] An array of disabled websocket events. Events in this array will not be
  * processed, potentially resulting in performance improvements for larger bots. Only disable events you are
@@ -42,6 +43,7 @@ exports.DefaultOptions = {
   disableEveryone: false,
   restWsBridgeTimeout: 5000,
   disabledEvents: [],
+  retryLimit: 1,
   restTimeOffset: 500,
   restSweepInterval: 60,
   presence: {},
diff --git a/typings/index.d.ts b/typings/index.d.ts
index 322691241..12f38f31e 100644
--- a/typings/index.d.ts
+++ b/typings/index.d.ts
@@ -1557,6 +1557,7 @@ declare module 'discord.js' {
 		disableEveryone?: boolean;
 		restWsBridgeTimeout?: number;
 		restTimeOffset?: number;
+		retryLimit?: number,
 		disabledEvents?: WSEventType[];
 		ws?: WebSocketOptions;
 		http?: HTTPOptions;