diff --git a/lib/twitter/rest/direct_messages.rb b/lib/twitter/rest/direct_messages.rb
index 362bd5e51..6561e2992 100644
--- a/lib/twitter/rest/direct_messages.rb
+++ b/lib/twitter/rest/direct_messages.rb
@@ -1,6 +1,7 @@
 require 'twitter/arguments'
 require 'twitter/direct_message'
 require 'twitter/direct_message_event'
+require 'twitter/rest/upload_utils'
 require 'twitter/rest/utils'
 require 'twitter/user'
 require 'twitter/utils'
@@ -8,6 +9,7 @@
 module Twitter
   module REST
     module DirectMessages
+      include Twitter::REST::UploadUtils
       include Twitter::REST::Utils
       include Twitter::Utils
 
@@ -192,6 +194,27 @@ def create_direct_message_event(*args)
         Twitter::DirectMessageEvent.new(response[:event])
       end
 
+      # Create a new direct message event to the specified user from the authenticating user with media
+      #
+      # @see https://developer.twitter.com/en/docs/direct-messages/sending-and-receiving/api-reference/new-event
+      # @see https://developer.twitter.com/en/docs/direct-messages/message-attachments/guides/attaching-media
+      # @note This method requires an access token with RWD (read, write & direct message) permissions. Consult The Application Permission Model for more information.
+      # @rate_limited Yes
+      # @authentication Requires user context
+      # @raise [Twitter::Error::Unauthorized] Error raised when supplied user credentials are not valid.
+      # @return [Twitter::DirectMessageEvent] The created direct message event.
+      # @param user [Integer, String, Twitter::User] A Twitter user ID, screen name, URI, or object.
+      # @param text [String] The text of your direct message, up to 10,000 characters.
+      # @param media [File] A media file (PNG, JPEG, GIF or MP4).
+      # @param options [Hash] A customizable set of options.
+      def create_direct_message_event_with_media(user, text, media, options = {})
+        media_id = upload(media, media_category_prefix: 'dm')[:media_id]
+        options = options.dup
+        options[:event] = {type: 'message_create', message_create: {target: {recipient_id: extract_id(user)}, message_data: {text: text, attachment: {type: 'media', media: {id: media_id}}}}}
+        response = Twitter::REST::Request.new(self, :json_post, '/1.1/direct_messages/events/new.json', options).perform
+        Twitter::DirectMessageEvent.new(response[:event])
+      end
+
     private
 
       def format_json_options(user_id, text, options)
diff --git a/lib/twitter/rest/tweets.rb b/lib/twitter/rest/tweets.rb
index e28644a5a..6fb21713b 100644
--- a/lib/twitter/rest/tweets.rb
+++ b/lib/twitter/rest/tweets.rb
@@ -2,6 +2,7 @@
 require 'twitter/error'
 require 'twitter/oembed'
 require 'twitter/rest/request'
+require 'twitter/rest/upload_utils'
 require 'twitter/rest/utils'
 require 'twitter/tweet'
 require 'twitter/utils'
@@ -9,6 +10,7 @@
 module Twitter
   module REST
     module Tweets
+      include Twitter::REST::UploadUtils
       include Twitter::REST::Utils
       include Twitter::Utils
       MAX_TWEETS_PER_REQUEST = 100
@@ -323,43 +325,6 @@ def unretweet(*args)
 
     private
 
-      # Uploads images and videos. Videos require multiple requests and uploads in chunks of 5 Megabytes.
-      # The only supported video format is mp4.
-      #
-      # @see https://dev.twitter.com/rest/public/uploading-media
-      def upload(media)
-        return chunk_upload(media, 'video/mp4', 'tweet_video') if File.extname(media) == '.mp4'
-        return chunk_upload(media, 'image/gif', 'tweet_gif') if File.extname(media) == '.gif' && File.size(media) > 5_000_000
-
-        Twitter::REST::Request.new(self, :multipart_post, 'https://upload.twitter.com/1.1/media/upload.json', key: :media, file: media).perform
-      end
-
-      # rubocop:disable MethodLength
-      def chunk_upload(media, media_type, media_category)
-        init = Twitter::REST::Request.new(self, :post, 'https://upload.twitter.com/1.1/media/upload.json',
-                                          command: 'INIT',
-                                          media_type: media_type,
-                                          media_category: media_category,
-                                          total_bytes: media.size).perform
-
-        until media.eof?
-          chunk = media.read(5_000_000)
-          seg ||= -1
-          Twitter::REST::Request.new(self, :multipart_post, 'https://upload.twitter.com/1.1/media/upload.json',
-                                     command: 'APPEND',
-                                     media_id: init[:media_id],
-                                     segment_index: seg += 1,
-                                     key: :media,
-                                     file: StringIO.new(chunk)).perform
-        end
-
-        media.close
-
-        Twitter::REST::Request.new(self, :post, 'https://upload.twitter.com/1.1/media/upload.json',
-                                   command: 'FINALIZE', media_id: init[:media_id]).perform
-      end
-      # rubocop:enable MethodLength
-
       def array_wrap(object)
         if object.respond_to?(:to_ary)
           object.to_ary || [object]
diff --git a/lib/twitter/rest/upload_utils.rb b/lib/twitter/rest/upload_utils.rb
new file mode 100644
index 000000000..d13839744
--- /dev/null
+++ b/lib/twitter/rest/upload_utils.rb
@@ -0,0 +1,46 @@
+require 'twitter/rest/request'
+
+module Twitter
+  module REST
+    module UploadUtils
+    private
+
+      # Uploads images and videos. Videos require multiple requests and uploads in chunks of 5 Megabytes.
+      # The only supported video format is mp4.
+      #
+      # @see https://dev.twitter.com/rest/public/uploading-media
+      def upload(media, media_category_prefix: 'tweet')
+        return chunk_upload(media, 'video/mp4', "#{media_category_prefix}_video") if File.extname(media) == '.mp4'
+        return chunk_upload(media, 'image/gif', "#{media_category_prefix}_gif") if File.extname(media) == '.gif' && File.size(media) > 5_000_000
+
+        Twitter::REST::Request.new(self, :multipart_post, 'https://upload.twitter.com/1.1/media/upload.json', key: :media, file: media).perform
+      end
+
+      # rubocop:disable MethodLength
+      def chunk_upload(media, media_type, media_category)
+        init = Twitter::REST::Request.new(self, :post, 'https://upload.twitter.com/1.1/media/upload.json',
+                                          command: 'INIT',
+                                          media_type: media_type,
+                                          media_category: media_category,
+                                          total_bytes: media.size).perform
+
+        until media.eof?
+          chunk = media.read(5_000_000)
+          seg ||= -1
+          Twitter::REST::Request.new(self, :multipart_post, 'https://upload.twitter.com/1.1/media/upload.json',
+                                     command: 'APPEND',
+                                     media_id: init[:media_id],
+                                     segment_index: seg += 1,
+                                     key: :media,
+                                     file: StringIO.new(chunk)).perform
+        end
+
+        media.close
+
+        Twitter::REST::Request.new(self, :post, 'https://upload.twitter.com/1.1/media/upload.json',
+                                   command: 'FINALIZE', media_id: init[:media_id]).perform
+      end
+      # rubocop:enable MethodLength
+    end
+  end
+end
diff --git a/spec/twitter/rest/direct_messages_spec.rb b/spec/twitter/rest/direct_messages_spec.rb
index 688a174b3..5515f3f43 100644
--- a/spec/twitter/rest/direct_messages_spec.rb
+++ b/spec/twitter/rest/direct_messages_spec.rb
@@ -165,4 +165,74 @@
       expect(direct_message_event.direct_message.text).to eq('testing')
     end
   end
+
+  describe '#create_direct_message_event_with_media' do
+    before do
+      stub_post('/1.1/direct_messages/events/new.json').to_return(body: fixture('direct_message_event.json'), headers: {content_type: 'application/json; charset=utf-8'})
+      stub_request(:post, 'https://upload.twitter.com/1.1/media/upload.json').to_return(body: fixture('upload.json'), headers: {content_type: 'application/json; charset=utf-8'})
+    end
+    context 'with a gif image' do
+      it 'requests the correct resource' do
+        @client.create_direct_message_event_with_media(58_983, 'testing', fixture('pbjt.gif'))
+        expect(a_request(:post, 'https://upload.twitter.com/1.1/media/upload.json')).to have_been_made
+        expect(a_post('/1.1/direct_messages/events/new.json')).to have_been_made
+      end
+      it 'returns a DirectMessageEvent' do
+        direct_message_event = @client.create_direct_message_event_with_media(58_983, 'testing', fixture('pbjt.gif'))
+        expect(direct_message_event).to be_a Twitter::DirectMessageEvent
+        expect(direct_message_event.direct_message.text).to eq('testing')
+      end
+      context 'which size is bigger than 5 megabytes' do
+        let(:big_gif) { fixture('pbjt.gif') }
+        before do
+          expect(File).to receive(:size).with(big_gif).and_return(7_000_000)
+        end
+        it 'requests the correct resource' do
+          @client.create_direct_message_event_with_media(58_983, 'testing', big_gif)
+          expect(a_request(:post, 'https://upload.twitter.com/1.1/media/upload.json')).to have_been_made.times(3)
+          expect(a_post('/1.1/direct_messages/events/new.json')).to have_been_made
+        end
+        it 'returns a DirectMessageEvent' do
+          direct_message_event = @client.create_direct_message_event_with_media(58_983, 'testing', big_gif)
+          expect(direct_message_event).to be_a Twitter::DirectMessageEvent
+          expect(direct_message_event.direct_message.text).to eq('testing')
+        end
+      end
+    end
+    context 'with a jpe image' do
+      it 'requests the correct resource' do
+        @client.create_direct_message_event_with_media(58_983, 'You always have options', fixture('wildcomet2.jpe'))
+        expect(a_request(:post, 'https://upload.twitter.com/1.1/media/upload.json')).to have_been_made
+        expect(a_post('/1.1/direct_messages/events/new.json')).to have_been_made
+      end
+    end
+    context 'with a jpeg image' do
+      it 'requests the correct resource' do
+        @client.create_direct_message_event_with_media(58_983, 'You always have options', fixture('me.jpeg'))
+        expect(a_request(:post, 'https://upload.twitter.com/1.1/media/upload.json')).to have_been_made
+        expect(a_post('/1.1/direct_messages/events/new.json')).to have_been_made
+      end
+    end
+    context 'with a png image' do
+      it 'requests the correct resource' do
+        @client.create_direct_message_event_with_media(58_983, 'You always have options', fixture('we_concept_bg2.png'))
+        expect(a_request(:post, 'https://upload.twitter.com/1.1/media/upload.json')).to have_been_made
+        expect(a_post('/1.1/direct_messages/events/new.json')).to have_been_made
+      end
+    end
+    context 'with a mp4 video' do
+      it 'requests the correct resources' do
+        @client.create_direct_message_event_with_media(58_983, 'You always have options', fixture('1080p.mp4'))
+        expect(a_request(:post, 'https://upload.twitter.com/1.1/media/upload.json')).to have_been_made.times(3)
+        expect(a_post('/1.1/direct_messages/events/new.json')).to have_been_made
+      end
+    end
+    context 'with a Tempfile' do
+      it 'requests the correct resource' do
+        @client.create_direct_message_event_with_media(58_983, 'You always have options', Tempfile.new('tmp'))
+        expect(a_request(:post, 'https://upload.twitter.com/1.1/media/upload.json')).to have_been_made
+        expect(a_post('/1.1/direct_messages/events/new.json')).to have_been_made
+      end
+    end
+  end
 end