diff --git a/public/script.js b/public/script.js
index bd3a39f54..9b8ab0c3f 100644
--- a/public/script.js
+++ b/public/script.js
@@ -3987,37 +3987,54 @@ export function replaceBiasMarkup(str) {
     return (str ?? '').replace(/\{\{[\s\S]*?\}\}/gm, '');
 }
 
-export async function sendMessageAsUser(textareaText, messageBias) {
-    textareaText = getRegexedString(textareaText, regex_placement.USER_INPUT);
+/**
+ * Inserts a user message into the chat history.
+ * @param {string} messageText Message text.
+ * @param {string} messageBias Message bias.
+ * @param {number} [insertAt] Optional index to insert the message at.
+ * @returns {Promise<void>} A promise that resolves when the message is inserted.
+ */
+export async function sendMessageAsUser(messageText, messageBias, insertAt = null) {
+    messageText = getRegexedString(messageText, regex_placement.USER_INPUT);
 
-    chat[chat.length] = {};
-    chat[chat.length - 1]['name'] = name1;
-    chat[chat.length - 1]['is_user'] = true;
-    chat[chat.length - 1]['send_date'] = getMessageTimeStamp();
-    chat[chat.length - 1]['mes'] = substituteParams(textareaText);
-    chat[chat.length - 1]['extra'] = {};
+    const message = {
+        name: name1,
+        is_user: true,
+        is_system: false,
+        send_date: getMessageTimeStamp(),
+        mes: substituteParams(messageText),
+        extra: {},
+    };
 
     if (power_user.message_token_count_enabled) {
-        chat[chat.length - 1]['extra']['token_count'] = getTokenCount(chat[chat.length - 1]['mes'], 0);
+        message.extra.token_count = getTokenCount(message.mes, 0);
     }
 
     // Lock user avatar to a persona.
     if (user_avatar in power_user.personas) {
-        chat[chat.length - 1]['force_avatar'] = getUserAvatar(user_avatar);
+        message.force_avatar = getUserAvatar(user_avatar);
     }
 
     if (messageBias) {
-        console.debug('checking bias');
-        chat[chat.length - 1]['extra']['bias'] = messageBias;
+        message.extra.bias = messageBias;
+    }
+
+    await populateFileAttachment(message);
+    statMesProcess(message, 'user', characters, this_chid, '');
+
+    if (typeof insertAt === 'number' && insertAt >= 0 && insertAt <= chat.length) {
+        chat.splice(insertAt, 0, message);
+        await saveChatConditional();
+        await eventSource.emit(event_types.MESSAGE_SENT, insertAt);
+        await reloadCurrentChat();
+        await eventSource.emit(event_types.USER_MESSAGE_RENDERED, insertAt);
+    } else {
+        chat.push(message);
+        const chat_id = (chat.length - 1);
+        await eventSource.emit(event_types.MESSAGE_SENT, chat_id);
+        addOneMessage(message);
+        await eventSource.emit(event_types.USER_MESSAGE_RENDERED, chat_id);
     }
-    await populateFileAttachment(chat[chat.length - 1]);
-    statMesProcess(chat[chat.length - 1], 'user', characters, this_chid, '');
-    // Wait for all handlers to finish before continuing with the prompt
-    const chat_id = (chat.length - 1);
-    await eventSource.emit(event_types.MESSAGE_SENT, chat_id);
-    addOneMessage(chat[chat_id]);
-    await eventSource.emit(event_types.USER_MESSAGE_RENDERED, chat_id);
-    console.debug('message sent as user');
 }
 
 function getMaxContextSize() {
diff --git a/public/scripts/slash-commands.js b/public/scripts/slash-commands.js
index bc4c1f266..af9c47f84 100644
--- a/public/scripts/slash-commands.js
+++ b/public/scripts/slash-commands.js
@@ -628,7 +628,7 @@ async function askCharacter(_, text) {
 
     setCharacterName(character.name);
 
-    sendMessageAsUser(mesText)
+    await sendMessageAsUser(mesText, '');
 
     const restoreCharacter = () => {
         setCharacterId(prevChId);
@@ -888,7 +888,7 @@ async function triggerGenerationCallback(_, arg) {
     return '';
 }
 
-async function sendUserMessageCallback(_, text) {
+async function sendUserMessageCallback(args, text) {
     if (!text) {
         console.warn('WARN: No text provided for /send command');
         return;
@@ -896,7 +896,8 @@ async function sendUserMessageCallback(_, text) {
 
     text = text.trim();
     const bias = extractMessageBias(text);
-    await sendMessageAsUser(text, bias);
+    const insertAt = Number(resolveVariable(args?.at));
+    await sendMessageAsUser(text, bias, insertAt);
     return '';
 }
 
@@ -1047,7 +1048,7 @@ async function setNarratorName(_, text) {
     await saveChatConditional();
 }
 
-export async function sendMessageAs(namedArgs, text) {
+export async function sendMessageAs(args, text) {
     if (!text) {
         return;
     }
@@ -1055,8 +1056,8 @@ export async function sendMessageAs(namedArgs, text) {
     let name;
     let mesText;
 
-    if (namedArgs.name) {
-        name = namedArgs.name.trim();
+    if (args.name) {
+        name = args.name.trim();
         mesText = text.trim();
 
         if (!name && !text) {
@@ -1107,14 +1108,24 @@ export async function sendMessageAs(namedArgs, text) {
         }
     };
 
-    chat.push(message);
-    await eventSource.emit(event_types.MESSAGE_RECEIVED, (chat.length - 1));
-    addOneMessage(message);
-    await eventSource.emit(event_types.CHARACTER_MESSAGE_RENDERED, (chat.length - 1));
-    await saveChatConditional();
+    const insertAt = Number(resolveVariable(args.at));
+
+    if (!isNaN(insertAt) && insertAt >= 0 && insertAt <= chat.length) {
+        chat.splice(insertAt, 0, message);
+        await saveChatConditional();
+        await eventSource.emit(event_types.MESSAGE_RECEIVED, insertAt);
+        await reloadCurrentChat();
+        await eventSource.emit(event_types.CHARACTER_MESSAGE_RENDERED, insertAt);
+    } else {
+        chat.push(message);
+        await eventSource.emit(event_types.MESSAGE_RECEIVED, (chat.length - 1));
+        addOneMessage(message);
+        await eventSource.emit(event_types.CHARACTER_MESSAGE_RENDERED, (chat.length - 1));
+        await saveChatConditional();
+    }
 }
 
-export async function sendNarratorMessage(_, text) {
+export async function sendNarratorMessage(args, text) {
     if (!text) {
         return;
     }
@@ -1138,11 +1149,21 @@ export async function sendNarratorMessage(_, text) {
         },
     };
 
-    chat.push(message);
-    await eventSource.emit(event_types.MESSAGE_SENT, (chat.length - 1));
-    addOneMessage(message);
-    await eventSource.emit(event_types.USER_MESSAGE_RENDERED, (chat.length - 1));
-    await saveChatConditional();
+    const insertAt = Number(resolveVariable(args.at));
+
+    if (!isNaN(insertAt) && insertAt >= 0 && insertAt <= chat.length) {
+        chat.splice(insertAt, 0, message);
+        await saveChatConditional();
+        await eventSource.emit(event_types.MESSAGE_SENT, insertAt);
+        await reloadCurrentChat();
+        await eventSource.emit(event_types.USER_MESSAGE_RENDERED, insertAt);
+    } else {
+        chat.push(message);
+        await eventSource.emit(event_types.MESSAGE_SENT, (chat.length - 1));
+        addOneMessage(message);
+        await eventSource.emit(event_types.USER_MESSAGE_RENDERED, (chat.length - 1));
+        await saveChatConditional();
+    }
 }
 
 export async function promptQuietForLoudResponse(who, text) {
@@ -1184,7 +1205,7 @@ export async function promptQuietForLoudResponse(who, text) {
 
 }
 
-async function sendCommentMessage(_, text) {
+async function sendCommentMessage(args, text) {
     if (!text) {
         return;
     }
@@ -1202,11 +1223,21 @@ async function sendCommentMessage(_, text) {
         },
     };
 
-    chat.push(message);
-    await eventSource.emit(event_types.MESSAGE_SENT, (chat.length - 1));
-    addOneMessage(message);
-    await eventSource.emit(event_types.USER_MESSAGE_RENDERED, (chat.length - 1));
-    await saveChatConditional();
+    const insertAt = Number(resolveVariable(args.at));
+
+    if (!isNaN(insertAt) && insertAt >= 0 && insertAt <= chat.length) {
+        chat.splice(insertAt, 0, message);
+        await saveChatConditional();
+        await eventSource.emit(event_types.MESSAGE_SENT, insertAt);
+        await reloadCurrentChat();
+        await eventSource.emit(event_types.USER_MESSAGE_RENDERED, insertAt);
+    } else {
+        chat.push(message);
+        await eventSource.emit(event_types.MESSAGE_SENT, (chat.length - 1));
+        addOneMessage(message);
+        await eventSource.emit(event_types.USER_MESSAGE_RENDERED, (chat.length - 1));
+        await saveChatConditional();
+    }
 }
 
 /**