diff --git a/app/controllers/twilio/callback_controller.rb b/app/controllers/twilio/callback_controller.rb
index ff5db952d..ff16e9386 100644
--- a/app/controllers/twilio/callback_controller.rb
+++ b/app/controllers/twilio/callback_controller.rb
@@ -24,9 +24,10 @@ class Twilio::CallbackController < ApplicationController
       :Body,
       :ToCountry,
       :FromState,
-      :MediaUrl0,
-      :MediaContentType0,
-      :MessagingServiceSid
+      *Array.new(10) { |i| :"MediaUrl#{i}" },
+      *Array.new(10) { |i| :"MediaContentType#{i}" },
+      :MessagingServiceSid,
+      :NumMedia
     )
   end
 end
diff --git a/app/services/twilio/incoming_message_service.rb b/app/services/twilio/incoming_message_service.rb
index 5c5854ee6..7a335c87d 100644
--- a/app/services/twilio/incoming_message_service.rb
+++ b/app/services/twilio/incoming_message_service.rb
@@ -106,15 +106,22 @@ class Twilio::IncomingMessageService
   end
 
   def attach_files
-    return if params[:MediaUrl0].blank?
+    num_media = params[:NumMedia].to_i
+    return if num_media.zero?
 
-    attachment_file = download_attachment_file
+    num_media.times do |i|
+      media_url = params[:"MediaUrl#{i}"]
+      attach_single_file(media_url) if media_url.present?
+    end
+  end
 
+  def attach_single_file(media_url)
+    attachment_file = download_attachment_file(media_url)
     return if attachment_file.blank?
 
     @message.attachments.new(
       account_id: @message.account_id,
-      file_type: file_type(params[:MediaContentType0]),
+      file_type: file_type(attachment_file.content_type),
       file: {
         io: attachment_file,
         filename: attachment_file.original_filename,
@@ -123,24 +130,22 @@ class Twilio::IncomingMessageService
     )
   end
 
-  def download_attachment_file
-    download_with_auth
+  def download_attachment_file(media_url)
+    download_with_auth(media_url)
   rescue Down::Error, Down::ClientError => e
-    handle_download_attachment_error(e)
+    handle_download_attachment_error(e, media_url)
   end
 
-  def download_with_auth
+  def download_with_auth(media_url)
     Down.download(
-      params[:MediaUrl0],
-      # https://support.twilio.com/hc/en-us/articles/223183748-Protect-Media-Access-with-HTTP-Basic-Authentication-for-Programmable-Messaging
+      media_url,
       http_basic_authentication: [twilio_channel.account_sid, twilio_channel.auth_token || twilio_channel.api_key_sid]
     )
   end
 
-  # This is just a temporary workaround since some users have not yet enabled media protection. We will remove this in the future.
-  def handle_download_attachment_error(error)
+  def handle_download_attachment_error(error, media_url)
     Rails.logger.info "Error downloading attachment from Twilio: #{error.message}: Retrying"
-    Down.download(params[:MediaUrl0])
+    Down.download(media_url)
   rescue StandardError => e
     Rails.logger.info "Error downloading attachment from Twilio: #{e.message}: Skipping"
     nil
diff --git a/spec/services/twilio/incoming_message_service_spec.rb b/spec/services/twilio/incoming_message_service_spec.rb
index 5f4dcec69..c8812e45d 100644
--- a/spec/services/twilio/incoming_message_service_spec.rb
+++ b/spec/services/twilio/incoming_message_service_spec.rb
@@ -173,7 +173,7 @@ describe Twilio::IncomingMessageService do
     context 'when a message with an attachment is received' do
       before do
         stub_request(:get, 'https://chatwoot-assets.local/sample.png')
-          .to_return(status: 200, body: 'image data', headers: {})
+          .to_return(status: 200, body: 'image data', headers: { 'Content-Type' => 'image/png' })
       end
 
       let(:params_with_attachment) do
@@ -203,7 +203,7 @@ describe Twilio::IncomingMessageService do
           .to_raise(Down::Error.new('Download error'))
 
         stub_request(:get, 'https://chatwoot-assets.local/sample.png')
-          .to_return(status: 200, body: 'image data', headers: {})
+          .to_return(status: 200, body: 'image data', headers: { 'Content-Type' => 'image/png' })
       end
 
       let(:params_with_attachment_error) do
@@ -229,5 +229,36 @@ describe Twilio::IncomingMessageService do
         expect(conversation.reload.messages.last.attachments.first.file_type).to eq('image')
       end
     end
+
+    context 'when a message with multiple attachments is received' do
+      before do
+        stub_request(:get, 'https://chatwoot-assets.local/sample.png')
+          .to_return(status: 200, body: 'image data 1', headers: { 'Content-Type' => 'image/png' })
+        stub_request(:get, 'https://chatwoot-assets.local/sample.jpg')
+          .to_return(status: 200, body: 'image data 2', headers: { 'Content-Type' => 'image/jpeg' })
+      end
+
+      let(:params_with_multiple_attachments) do
+        {
+          SmsSid: 'SMxx',
+          From: '+12345',
+          AccountSid: 'ACxxx',
+          MessagingServiceSid: twilio_channel.messaging_service_sid,
+          Body: 'testing multiple media',
+          NumMedia: '2',
+          MediaContentType0: 'image/png',
+          MediaUrl0: 'https://chatwoot-assets.local/sample.png',
+          MediaContentType1: 'image/jpeg',
+          MediaUrl1: 'https://chatwoot-assets.local/sample.jpg'
+        }
+      end
+
+      it 'creates a new message with multiple media attachments in existing conversation' do
+        described_class.new(params: params_with_multiple_attachments).perform
+        expect(conversation.reload.messages.last.content).to eq('testing multiple media')
+        expect(conversation.reload.messages.last.attachments.count).to eq(2)
+        expect(conversation.reload.messages.last.attachments.map(&:file_type)).to contain_exactly('image', 'image')
+      end
+    end
   end
 end