diff --git a/src/execution.ts b/src/execution.ts
index f1b332c..38699eb 100644
--- a/src/execution.ts
+++ b/src/execution.ts
@@ -1,5 +1,6 @@
 import DiscordApi, { GuildTextBasedChannel } from "discord.js";
 import { ChatCompletionRequestMessage, ChatCompletionResponseMessage } from "openai";
+import Axios from "axios";
 
 import { database, openai } from "./index";
 import Moderation from "./moderation";
@@ -9,13 +10,19 @@ import FunctionManager from "./funcitonManager";
 
 type NonNullableInObject<T, V> = { [k in keyof T]: k extends V ? NonNullable<T[k]> : T[k] };
 type apiRequest = DiscordApi.Message | DiscordApi.RepliableInteraction;
-export type request = apiRequest & NonNullableInObject<apiRequest, "channel" | "channelId">;
+export type RequestMessage = apiRequest & NonNullableInObject<apiRequest, "channel" | "channelId">;
+
+class ChannelsRunningValue extends Array<RequestMessage> {
+  tries = 0;
+
+  shift() {
+    this.tries = 0;
+    return super.shift();
+  }
+}
 
 /** Stores the queue requests on the channels. */
-const channelsRunning: DiscordApi.Collection<string, request[]> = new DiscordApi.Collection();
-
-type ChannelQueue = NonNullable<ReturnType<typeof channelsRunning.get>>;
-type RequestMessage = NonNullable<ReturnType<ChannelQueue["at"]>>;
+const channelsRunning: DiscordApi.Collection<string, ChannelsRunningValue> = new DiscordApi.Collection();
 
 /**
  * Gets the user that requested the execution
@@ -99,7 +106,7 @@ export async function getNthUseInLimitTimestamp(user: string | { id: string }, r
  * @returns Promise of the done action
  */
 function requestReply(
-  request: request,
+  request: RequestMessage,
   message: DiscordApi.MessageReplyOptions & DiscordApi.InteractionReplyOptions,
   // TODO: add support for these below
   replyOptions: DiscordApi.MessageReplyOptions = {},
@@ -170,10 +177,10 @@ export async function queueRequest(request: apiRequest) {
 
   const messagesForChannel = channelsRunning.ensure(
     request.channelId,
-    () => { return []; },
+    () => { return new ChannelsRunningValue; },
   );
   const shouldStart = messagesForChannel.length === 0;
-  messagesForChannel.push(request as request);
+  messagesForChannel.push(request as RequestMessage);
   if (shouldStart)
     void executeFromQueue(request.channelId);
 }
@@ -218,7 +225,7 @@ function logUsedTokens(
  * @param channel the channel to run the queue for
  */
 async function executeFromQueue(channel: string) {
-  const channelQueue = channelsRunning.get(channel) as ChannelQueue;
+  const channelQueue = channelsRunning.get(channel) as ChannelsRunningValue;
   const message = channelQueue.at(0) as RequestMessage;
   let functionRanCounter = 0;
   let OpenAImessages: ChatCompletionRequestMessage[] = [];
@@ -303,6 +310,10 @@ async function executeFromQueue(channel: string) {
       errorText += e.message;
     }
     else errorText = "";
+    if (Axios.isAxiosError(e) && e.code?.match(/^5..$/) && channelQueue.tries < 3) {
+      channelQueue.tries++;
+      return executeFromQueue(channel);
+    }
 
     await requestReply(
       message,
diff --git a/src/toOpenAIMessages.ts b/src/toOpenAIMessages.ts
index 0d5e1c2..598238d 100644
--- a/src/toOpenAIMessages.ts
+++ b/src/toOpenAIMessages.ts
@@ -4,14 +4,14 @@ import FoldToAscii from "fold-to-ascii";
 
 import config from "./config";
 import countTokens from "./tokenCounter";
-import { request } from "./execution";
+import { RequestMessage } from "./execution";
 
 /**
  * formats the request to use as a message contend in OpenAI api
  * @param request the request to format
  * @returns the formatted request
  */
-export async function formatRequestOrResponse(request: request | InteractionResponse): Promise<string> {
+export async function formatRequestOrResponse(request: RequestMessage | InteractionResponse): Promise<string> {
   if (request instanceof DiscordMessage) {
     return formatMessage(request);
   }