diff --git a/src/execution.ts b/src/execution.ts
index 57a5463..fec4160 100644
--- a/src/execution.ts
+++ b/src/execution.ts
@@ -267,6 +267,7 @@ async function executeFromQueue(channel: string) {
 
     messages.forEach(m => { Moderation.checkMessageNoReturn(m); });
 
+    const questionMessageId: string = message instanceof DiscordApi.Message ? message.id : '';
     if (message instanceof DiscordApi.Message) {
       channelQueue.startTyping();
     }
@@ -274,7 +275,13 @@ async function executeFromQueue(channel: string) {
       await message.deferReply();
     }
 
-    OpenAImessages = toOpenAIMessages(messages);
+    messages.sort((a, b) => {
+      if (a.id === questionMessageId) return -1;
+      if (b.id === questionMessageId) return 1;
+      return b.createdTimestamp - a.createdTimestamp;
+    });
+
+    OpenAImessages = toOpenAIMessages(messages.values());
     let generatedMessage: ChatCompletionResponseMessage | undefined = undefined;
     let answer: Awaited<ReturnType<typeof openai.createChatCompletion>>;
 
diff --git a/src/toOpenAIMessages.ts b/src/toOpenAIMessages.ts
index 598238d..e868b45 100644
--- a/src/toOpenAIMessages.ts
+++ b/src/toOpenAIMessages.ts
@@ -92,17 +92,18 @@ function getAuthorUsername(message: DiscordMessage): string | undefined {
 }
 
 /**
- * Converts the Collection of Discord Messages to array of OpenAI Messages to send
- * @param messages the collection to convert
+ * Converts the Iterable of Discord Messages to array of OpenAI Messages to send
+ * first message in the interable will be the last of the returned array (reverse order)
+ * @param messages the iterable to convert
  * @returns the converted messages
  */
-export default function toOpenAIMessages(messages: Collection<string, DiscordMessage>): OpenAIMessage[] {
+export default function toOpenAIMessages(
+  messages: Iterable<DiscordMessage>,
+): OpenAIMessage[] {
   const rvalue: OpenAIMessage[] = [];
   let tokenCount = 0;
 
-  messages.sort((a, b) => b.createdTimestamp - a.createdTimestamp);
-
-  for (const message of messages.values()) {
+  for (const message of messages) {
     const content = formatMessage(message);
     // FIXME: tokens are not being counted properly (it's lower than it is) but it's enough for me for now.
     tokenCount += countTokens(content);