diff --git a/app/livechat/server/sendMessageBySMS.js b/app/livechat/server/sendMessageBySMS.js
index 722ccd92e2e..cbceda93baf 100644
--- a/app/livechat/server/sendMessageBySMS.js
+++ b/app/livechat/server/sendMessageBySMS.js
@@ -29,9 +29,11 @@ callbacks.add('afterSaveMessage', function(message, room) {
 		return message;
 	}
 
-
+	let extraData;
 	if (message.file) {
 		message = normalizeMessageFileUpload(message);
+		const { fileUpload, rid, u: { _id: userId } = {} } = message;
+		extraData = Object.assign({}, { rid, userId, fileUpload });
 	}
 
 	const SMSService = SMS.getService(settings.get('SMS_Service'));
@@ -46,7 +48,7 @@ callbacks.add('afterSaveMessage', function(message, room) {
 		return message;
 	}
 
-	SMSService.send(room.sms.from, visitor.phone[0].phoneNumber, message.msg);
+	SMSService.send(room.sms.from, visitor.phone[0].phoneNumber, message.msg, extraData);
 
 	return message;
 }, callbacks.priority.LOW, 'sendMessageBySms');
diff --git a/app/sms/server/services/twilio.js b/app/sms/server/services/twilio.js
index b4221c2b2f4..67920e13145 100644
--- a/app/sms/server/services/twilio.js
+++ b/app/sms/server/services/twilio.js
@@ -1,12 +1,29 @@
+import { Meteor } from 'meteor/meteor';
 import twilio from 'twilio';
+import { Random } from 'meteor/random';
+import { TAPi18n } from 'meteor/rocketchat:tap-i18n';
+import filesize from 'filesize';
 
 import { settings } from '../../../settings';
 import { SMS } from '../SMS';
+import { Notifications } from '../../../notifications';
+import { fileUploadIsValidContentType } from '../../../utils/lib/fileUploadRestrictions';
+
+const MAX_FILE_SIZE = 5242880;
+
+const notifyAgent = (userId, rid, msg) => Notifications.notifyUser(userId, 'message', {
+	_id: Random.id(),
+	rid,
+	ts: new Date(),
+	msg,
+});
 
 class Twilio {
 	constructor() {
 		this.accountSid = settings.get('SMS_Twilio_Account_SID');
 		this.authToken = settings.get('SMS_Twilio_authToken');
+		this.fileUploadEnabled = settings.get('SMS_Twilio_FileUpload_Enabled');
+		this.mediaTypeWhiteList = settings.get('SMS_Twilio_FileUpload_MediaTypeWhiteList');
 	}
 
 	parse(data) {
@@ -58,13 +75,40 @@ class Twilio {
 		return returnData;
 	}
 
-	send(fromNumber, toNumber, message) {
+	send(fromNumber, toNumber, message, extraData) {
 		const client = twilio(this.accountSid, this.authToken);
 
+		let mediaUrl;
+		if (extraData && extraData.fileUpload) {
+			const { rid, userId, fileUpload: { size, type, publicFilePath } } = extraData;
+			const user = userId ? Meteor.users.findOne(userId) : null;
+			const lng = (user && user.language) || settings.get('Language') || 'en';
+
+			let reason;
+			if (!this.fileUploadEnabled) {
+				reason = TAPi18n.__('FileUpload_Disabled', { lng });
+			} else if (size > MAX_FILE_SIZE) {
+				reason = TAPi18n.__('File_exceeds_allowed_size_of_bytes', {
+					size: filesize(MAX_FILE_SIZE),
+					lng,
+				});
+			} else if (!fileUploadIsValidContentType(type, this.fileUploadMediaTypeWhiteList)) {
+				reason = TAPi18n.__('File_type_is_not_accepted', { lng });
+			}
+
+			if (reason) {
+				rid && userId && notifyAgent(userId, rid, reason);
+				return console.error(`(Twilio) -> ${ reason }`);
+			}
+
+			mediaUrl = [publicFilePath];
+		}
+		// return
 		client.messages.create({
 			to: toNumber,
 			from: fromNumber,
 			body: message,
+			...mediaUrl && { mediaUrl },
 		});
 	}
 
diff --git a/app/sms/server/settings.js b/app/sms/server/settings.js
index 80b06946ef9..466df5d8c65 100644
--- a/app/sms/server/settings.js
+++ b/app/sms/server/settings.js
@@ -47,6 +47,25 @@ Meteor.startup(function() {
 				i18nLabel: 'Auth_Token',
 				secret: true,
 			});
+			this.add('SMS_Twilio_FileUpload_Enabled', true, {
+				type: 'boolean',
+				enableQuery: {
+					_id: 'SMS_Service',
+					value: 'twilio',
+				},
+				i18nLabel: 'FileUpload_Enabled',
+				secret: true,
+			});
+			this.add('SMS_Twilio_FileUpload_MediaTypeWhiteList', 'image/*,audio/*,video/*,text/*,application/pdf', {
+				type: 'string',
+				enableQuery: {
+					_id: 'SMS_Service',
+					value: 'twilio',
+				},
+				i18nLabel: 'FileUpload_MediaTypeWhiteList',
+				i18nDescription: 'FileUpload_MediaTypeWhiteListDescription',
+				secret: true,
+			});
 		});
 
 		this.section('Voxtelesys', function() {
diff --git a/package.json b/package.json
index 385f636ec2d..01088ac51b1 100644
--- a/package.json
+++ b/package.json
@@ -220,7 +220,7 @@
 		"tar-stream": "^1.6.2",
 		"toastr": "^2.1.4",
 		"turndown": "^5.0.1",
-		"twilio": "^3.25.0",
+		"twilio": "^3.35.0",
 		"twit": "^2.2.11",
 		"ua-parser-js": "^0.7.19",
 		"underscore": "^1.9.1",