diff --git a/src/client/actions/MessageCreate.js b/src/client/actions/MessageCreate.js
index 10626179c..1280d991a 100644
--- a/src/client/actions/MessageCreate.js
+++ b/src/client/actions/MessageCreate.js
@@ -5,12 +5,22 @@ class MessageCreateAction extends Action {
   handle(data) {
     const client = this.client;
 
-    const channel = client.channels.get(data.channel_id);
+    const channel = client.channels.get((data instanceof Array ? data[0] : data).channel_id);
     if (channel) {
-      const message = channel._cacheMessage(new Message(channel, data, client));
-      return {
-        message,
-      };
+      if (data instanceof Array) {
+        const messages = new Array(data.length);
+        for (let i = 0; i < data.length; i++) {
+          messages[i] = channel._cacheMessage(new Message(channel, data[i], client));
+        }
+        return {
+          messages,
+        };
+      } else {
+        const message = channel._cacheMessage(new Message(channel, data, client));
+        return {
+          message,
+        };
+      }
     }
 
     return {
diff --git a/src/client/rest/RESTMethods.js b/src/client/rest/RESTMethods.js
index e878ccd61..bc588e253 100644
--- a/src/client/rest/RESTMethods.js
+++ b/src/client/rest/RESTMethods.js
@@ -1,5 +1,6 @@
 const Constants = require('../../util/Constants');
 const Collection = require('../../util/Collection');
+const splitMessage = require('../../util/SplitMessage');
 
 const requireStructure = name => require(`../../structures/${name}`);
 const User = requireStructure('User');
@@ -46,36 +47,58 @@ class RESTMethods {
     });
   }
 
-  sendMessage(channel, content, tts, nonce, disableEveryone, file) {
+  sendMessage(channel, content, { tts, nonce, disable_everyone, split } = {}, file = null) {
     return new Promise((resolve, reject) => {
-      const $this = this;
-
       if (typeof content !== 'undefined') content = this.rest.client.resolver.resolveString(content);
 
-      if (disableEveryone || (typeof disableEveryone === 'undefined' && this.rest.client.options.disable_everyone)) {
+      if (disable_everyone || (typeof disable_everyone === 'undefined' && this.rest.client.options.disable_everyone)) {
         content = content.replace('@everyone', '@\u200beveryone').replace('@here', '@\u200bhere');
       }
 
-      function req() {
-        $this.rest.makeRequest('post', Constants.Endpoints.channelMessages(channel.id), true, {
-          content, tts, nonce,
-        }, file)
-        .then(data => resolve($this.rest.client.actions.MessageCreate.handle(data).message))
-        .catch(reject);
-      }
+      if (split) content = splitMessage(content, typeof split === 'object' ? split : {});
 
       if (channel instanceof User || channel instanceof GuildMember) {
         this.createDM(channel).then(chan => {
           channel = chan;
-          req();
+          this._sendMessageRequest(channel, content, file, tts, nonce, resolve, reject);
         })
         .catch(reject);
       } else {
-        req();
+        this._sendMessageRequest(channel, content, file, tts, nonce, resolve, reject);
       }
     });
   }
 
+  _sendMessageRequest(channel, content, file, tts, nonce, resolve, reject) {
+    if (content instanceof Array) {
+      const datas = [];
+      const promise = this.rest.makeRequest('post', Constants.Endpoints.channelMessages(channel.id), true, {
+        content: content[0], tts, nonce,
+      }, file);
+      for (let i = 1; i <= content.length; i++) {
+        if (i < content.length) {
+          promise.then(data => {
+            datas.push(data);
+            return this.rest.makeRequest('post', Constants.Endpoints.channelMessages(channel.id), true, {
+              content: content[i], tts, nonce,
+            }, file);
+          });
+        } else {
+          promise.then(data => {
+            datas.push(data);
+            resolve(this.rest.client.actions.MessageCreate.handle(datas).messages).catch(reject);
+          });
+        }
+      }
+    } else {
+      this.rest.makeRequest('post', Constants.Endpoints.channelMessages(channel.id), true, {
+        content, tts, nonce,
+      }, file)
+        .then(data => resolve(this.rest.client.actions.MessageCreate.handle(data).message))
+        .catch(reject);
+    }
+  }
+
   deleteMessage(message) {
     return new Promise((resolve, reject) => {
       this.rest.makeRequest('del', Constants.Endpoints.channelMessage(message.channel.id, message.id), true)
diff --git a/src/structures/Message.js b/src/structures/Message.js
index edca03498..f4bd63b54 100644
--- a/src/structures/Message.js
+++ b/src/structures/Message.js
@@ -290,7 +290,7 @@ class Message {
    * Reply to a message
    * @param {StringResolvable} content The content for the message
    * @param {MessageOptions} [options = {}] The options to provide
-   * @returns {Promise<Message>}
+   * @returns {Promise<Message|Message[]>}
    * @example
    * // reply to a message
    * message.reply('Hey, I'm a reply!')
@@ -299,8 +299,15 @@ class Message {
    */
   reply(content, options = {}) {
     content = this.client.resolver.resolveString(content);
-    const newContent = this.guild ? `${this.author}, ${content}` : content;
-    return this.client.rest.methods.sendMessage(this.channel, newContent, options.tts);
+    const prepend = this.guild ? `${this.author}, ` : '';
+    content = `${prepend}${content}`;
+
+    if (options.split) {
+      if (typeof options.split !== 'object') options.split = {};
+      if (!options.split.prepend) options.split.prepend = prepend;
+    }
+
+    return this.client.rest.methods.sendMessage(this.channel, content, options);
   }
 
   /**
diff --git a/src/structures/interface/TextBasedChannel.js b/src/structures/interface/TextBasedChannel.js
index 5f11e285e..4794be920 100644
--- a/src/structures/interface/TextBasedChannel.js
+++ b/src/structures/interface/TextBasedChannel.js
@@ -29,6 +29,7 @@ class TextBasedChannel {
    *   tts: false,
    *   nonce: '',
    *   disable_everyone: false,
+   *   split: false,
    * };
    * ```
    * @typedef {Object} MessageOptions
@@ -38,7 +39,7 @@ class TextBasedChannel {
    * Send a message to this channel
    * @param {StringResolvable} content The content to send
    * @param {MessageOptions} [options={}] The options to provide
-   * @returns {Promise<Message>}
+   * @returns {Promise<Message|Message[]>}
    * @example
    * // send a message
    * channel.sendMessage('hello!')
@@ -46,14 +47,14 @@ class TextBasedChannel {
    *  .catch(console.log);
    */
   sendMessage(content, options = {}) {
-    return this.client.rest.methods.sendMessage(this, content, options.tts, options.nonce, options.disable_everyone);
+    return this.client.rest.methods.sendMessage(this, content, options);
   }
 
   /**
    * Send a text-to-speech message to this channel
    * @param {StringResolvable} content The content to send
    * @param {MessageOptions} [options={}] The options to provide
-   * @returns {Promise<Message>}
+   * @returns {Promise<Message|Message[]>}
    * @example
    * // send a TTS message
    * channel.sendTTSMessage('hello!')
@@ -61,7 +62,8 @@ class TextBasedChannel {
    *  .catch(console.log);
    */
   sendTTSMessage(content, options = {}) {
-    return this.client.rest.methods.sendMessage(this, content, true, options.nonce, options.disable_everyone);
+    Object.assign(options, { tts: true });
+    return this.client.rest.methods.sendMessage(this, content, options);
   }
 
   /**
@@ -69,9 +71,10 @@ class TextBasedChannel {
    * @param {FileResolvable} attachment The file to send
    * @param {string} [fileName="file.jpg"] The name and extension of the file
    * @param {StringResolvable} [content] Text message to send with the attachment
+   * @param {MessageOptions} [options] The options to provide
    * @returns {Promise<Message>}
    */
-  sendFile(attachment, fileName, content) {
+  sendFile(attachment, fileName, content, options = {}) {
     if (!fileName) {
       if (typeof attachment === 'string') {
         fileName = path.basename(attachment);
@@ -83,7 +86,7 @@ class TextBasedChannel {
     }
     return new Promise((resolve, reject) => {
       this.client.resolver.resolveFile(attachment).then(file => {
-        this.client.rest.methods.sendMessage(this, content, false, undefined, false, {
+        this.client.rest.methods.sendMessage(this, content, options, {
           file,
           name: fileName,
         }).then(resolve).catch(reject);
diff --git a/src/util/SplitMessage.js b/src/util/SplitMessage.js
new file mode 100644
index 000000000..3833f009a
--- /dev/null
+++ b/src/util/SplitMessage.js
@@ -0,0 +1,16 @@
+module.exports = function splitMessage(text, { maxLength = 1950, char = '\n', prepend = '', append = '' } = {}) {
+  if (text.length <= maxLength) return text;
+  const splitText = text.split(char);
+  if (splitText.length === 1) throw new Error('Message exceeds the max length and contains no split characters.');
+  const messages = [''];
+  let msg = 0;
+  for (let i = 0; i < splitText.length; i++) {
+    if (messages[msg].length + splitText[i].length + 1 > maxLength) {
+      messages[msg] += append;
+      messages.push(prepend);
+      msg++;
+    }
+    messages[msg] += (messages[msg].length > 0 && messages[msg] !== prepend ? char : '') + splitText[i];
+  }
+  return messages;
+};