diff --git a/app/adapters/whats_app_adapter/three_sixty_dialog_outbound.rb b/app/adapters/whats_app_adapter/three_sixty_dialog_outbound.rb
index 6015f95c1..2e425f3cd 100644
--- a/app/adapters/whats_app_adapter/three_sixty_dialog_outbound.rb
+++ b/app/adapters/whats_app_adapter/three_sixty_dialog_outbound.rb
@@ -112,10 +112,8 @@ def send_message_template(recipient, message)
       end
 
       def send_message(recipient, message)
-        files = message.files
-
-        if files.present?
-          WhatsAppAdapter::ThreeSixtyDialogOutbound::File.perform_later(message_id: message.id) if files.present?
+        if message.files.present?
+          WhatsAppAdapter::ThreeSixtyDialogOutbound::File.perform_later(message_id: message.id)
 
         else
 
diff --git a/app/adapters/whats_app_adapter/three_sixty_dialog_outbound/file.rb b/app/adapters/whats_app_adapter/three_sixty_dialog_outbound/file.rb
index 33b5b97b6..82852eae7 100644
--- a/app/adapters/whats_app_adapter/three_sixty_dialog_outbound/file.rb
+++ b/app/adapters/whats_app_adapter/three_sixty_dialog_outbound/file.rb
@@ -8,8 +8,6 @@ class File < ApplicationJob
       # rubocop:disable Metrics/AbcSize
       def perform(message_id:)
         @message = Message.find(message_id)
-        organization = Organization.find(message.organization.id)
-
         @recipient = message.recipient
 
         unless caption_it?
@@ -19,7 +17,7 @@ def perform(message_id:)
 
         message.request.external_file_ids.each do |file_id|
           url = URI.parse("#{ENV.fetch('THREE_SIXTY_DIALOG_WHATS_APP_REST_API_ENDPOINT', 'https://stoplight.io/mocks/360dialog/360dialog-partner-api/24588693')}/messages")
-          headers = { 'D360-API-KEY' => organization.three_sixty_dialog_client_api_key, 'Content-Type' => 'application/json' }
+          headers = { 'D360-API-KEY' => message.organization.three_sixty_dialog_client_api_key, 'Content-Type' => 'application/json' }
           request = Net::HTTP::Post.new(url.to_s, headers)
           body = payload(file_id)
           body[:image][:caption] = message.text if caption_it?
diff --git a/app/controllers/whats_app/three_sixty_dialog_webhook_controller.rb b/app/controllers/whats_app/three_sixty_dialog_webhook_controller.rb
index 7632f00d1..1689a03f1 100644
--- a/app/controllers/whats_app/three_sixty_dialog_webhook_controller.rb
+++ b/app/controllers/whats_app/three_sixty_dialog_webhook_controller.rb
@@ -7,8 +7,8 @@ class ThreeSixtyDialogWebhookController < ApplicationController
 
     def message
       head :ok
-      handle_error(@components[:statuses].first[:errors].first) and return if @components[:statuses]&.first[:errors].present?
-      return if @components[:statuses].present? # TODO: Handle statuses
+      handle_statuses and return if @components[:statuses].present? # TODO: Handle statuses
+      handle_errors(@components[:errors]) and return if @components[:errors].present?
 
       WhatsAppAdapter::ThreeSixtyDialog::ProcessWebhookJob.perform_later(organization_id: @organization.id, components: @components)
     end
@@ -24,8 +24,8 @@ def message_params
                     entry: [:id, {
                       changes: [:field, {
                         value: [:messaging_product,
-                                { metadata: %i[display_phone_number phone_number_id] },
-                                { contacts: [:wa_id, { profile: [:name] }],
+                                { metadata: %i[display_phone_number phone_number_id],
+                                  contacts: [:wa_id, { profile: [:name] }],
                                   messages: [:from, :id, :type, :timestamp,
                                              { text: [:body] }, { button: %i[payload text] },
                                              { image: %i[id mime_type sha256 caption] }, { voice: %i[id mime_type sha256] },
@@ -38,16 +38,26 @@ def message_params
                                              { context: %i[from id] }],
                                   statuses: [:id, :status, :timestamp, :expiration_timestamp, :recipient_id,
                                              { conversation: [:id, { origin: [:type] }] },
-                                             { pricing: %i[billable pricing_model category],
-                                               errors: [:code, :title, :message, :href, { error_data: [:details] }] }] }]
+                                             { pricing: %i[billable pricing_model category] },
+                                             { errors: [:code, :title, :message, :href, { error_data: [:details] }] }],
+                                  errors: [:code, :title, :message, :href, { error_data: [:details] }] }]
 
                       }]
                     }])
     end
 
-    def handle_error(error)
-      exception = WhatsAppAdapter::ThreeSixtyDialogError.new(error_code: error[:code], message: error[:title])
-      ErrorNotifier.report(exception, context: { details: error[:error_data][:details] })
+    def handle_statuses
+      statuses = @components[:statuses]
+      statuses.each do |status|
+        handle_errors(status[:errors]) if status[:errors]
+      end
+    end
+
+    def handle_errors(errors)
+      errors.each do |error|
+        exception = WhatsAppAdapter::ThreeSixtyDialogError.new(error_code: error[:code], message: error[:title])
+        ErrorNotifier.report(exception, context: { details: error[:error_data][:details] })
+      end
     end
   end
 end
diff --git a/spec/adapters/whats_app_adapter/three_sixty_dialog_outbound_spec.rb b/spec/adapters/whats_app_adapter/three_sixty_dialog_outbound_spec.rb
index 4d5aa17cc..87c20572b 100644
--- a/spec/adapters/whats_app_adapter/three_sixty_dialog_outbound_spec.rb
+++ b/spec/adapters/whats_app_adapter/three_sixty_dialog_outbound_spec.rb
@@ -123,12 +123,14 @@
         end
 
         context 'contributor has sent a reply within 24 hours' do
-          before { create(:message, sender: contributor) }
+          before do
+            create(:message, sender: contributor)
+          end
 
           it 'enqueues a File job with file, contributor, text' do
             expect do
               subject.call
-            end.to(have_enqueued_job(WhatsAppAdapter::ThreeSixtyDialog::UploadFileJob).on_queue('default').with do |params|
+            end.to(have_enqueued_job(WhatsAppAdapter::ThreeSixtyDialogOutbound::File).on_queue('default').with do |params|
                      expect(params[:message_id]).to eq(message.id)
                    end)
           end
diff --git a/spec/jobs/whats_app_adapter/three_sixty_dialog/process_webhook_job_spec.rb b/spec/jobs/whats_app_adapter/three_sixty_dialog/process_webhook_job_spec.rb
index 1dc731ad7..334ad0d9c 100644
--- a/spec/jobs/whats_app_adapter/three_sixty_dialog/process_webhook_job_spec.rb
+++ b/spec/jobs/whats_app_adapter/three_sixty_dialog/process_webhook_job_spec.rb
@@ -78,6 +78,17 @@
           end
 
           describe 'with no external id' do
+            let(:base_uri) { 'https://waba-v2.360dialog.io' }
+            let(:external_file_id) { '545466424653131' }
+
+            before do
+              latest_message.request.update!(external_file_ids: [external_file_id])
+              allow(ENV).to receive(:fetch).with(
+                'THREE_SIXTY_DIALOG_WHATS_APP_REST_API_ENDPOINT', 'https://stoplight.io/mocks/360dialog/360dialog-partner-api/24588693'
+              ).and_return(base_uri)
+              stub_request(:post, "#{base_uri}/messages").to_return(status: 200, body: { messages: [id: 'some_external_id'] }.to_json)
+            end
+
             it 'enqueues a job to send the latest received message' do
               expect do
                 subject.call
@@ -86,26 +97,32 @@
               )
             end
 
+            it 'updates the message with the external id' do
+              perform_enqueued_jobs(only: WhatsAppAdapter::ThreeSixtyDialogOutbound::Text) do
+                expect { subject.call }.to (change { latest_message.reload.external_id }).from(nil).to('some_external_id')
+              end
+            end
+
             context 'message with file, no text' do
               let(:message_file) do
                 [create(:file, message: latest_message,
                                attachment: Rack::Test::UploadedFile.new(Rails.root.join('spec/fixtures/files/matt.jpeg'), 'image/jpeg'))]
               end
-              let(:external_file_id) { '545466424653131' }
 
               before do
                 latest_message.update!(text: '', files: message_file)
-                allow(ENV).to receive(:fetch).with(
-                  'THREE_SIXTY_DIALOG_WHATS_APP_REST_API_ENDPOINT', 'https://stoplight.io/mocks/360dialog/360dialog-partner-api/24588693'
-                ).and_return('https://waba-v2.360dialog.io')
               end
 
               it 'enqueues a job to send the file' do
-                expect { subject.call }.to have_enqueued_job(WhatsAppAdapter::ThreeSixtyDialog::UploadFileJob)
-                  .and have_enqueued_job(WhatsAppAdapter::ThreeSixtyDialogOutbound::File).with({
-                                                                                                 message_id: latest_message.id,
-                                                                                                 file_id: external_file_id
-                                                                                               })
+                expect { subject.call }.to have_enqueued_job(
+                  WhatsAppAdapter::ThreeSixtyDialogOutbound::File
+                ).with({ message_id: latest_message.id })
+              end
+
+              it 'updates the message with the external id' do
+                perform_enqueued_jobs(only: WhatsAppAdapter::ThreeSixtyDialogOutbound::File) do
+                  expect { subject.call }.to (change { latest_message.reload.external_id }).from(nil).to('some_external_id')
+                end
               end
 
               context 'message with file and text' do
@@ -116,17 +133,23 @@
                 it 'enqueues a job to upload the file' do
                   expect do
                     subject.call
-                  end.to have_enqueued_job(WhatsAppAdapter::ThreeSixtyDialog::UploadFileJob).on_queue('default').with(
+                  end.to have_enqueued_job(WhatsAppAdapter::ThreeSixtyDialogOutbound::File).on_queue('default').with(
                     message_id: latest_message.id
                   )
                 end
 
-                it 'enqueues a job to send out the text' do
-                  expect do
-                    subject.call
-                  end.to have_enqueued_job(WhatsAppAdapter::ThreeSixtyDialogOutbound::Text).on_queue('default').with(
-                    text_payload.merge({ message_id: latest_message.id })
-                  )
+                context 'given the text is greater than 1024' do
+                  before { latest_message.update!(text: Faker::Lorem.characters(number: 1025)) }
+
+                  it 'enqueues a job to send out the text' do
+                    perform_enqueued_jobs(only: WhatsAppAdapter::ThreeSixtyDialogOutbound::File) do
+                      expect do
+                        subject.call
+                      end.to have_enqueued_job(WhatsAppAdapter::ThreeSixtyDialogOutbound::Text).on_queue('default').with(
+                        text_payload.merge({ message_id: latest_message.id })
+                      )
+                    end
+                  end
                 end
               end
             end
diff --git a/spec/jobs/whats_app_adapter/three_sixty_dialog/upload_file_job_spec.rb b/spec/services/whats_app_adapter/three_sixty_dialog/upload_file_service_spec.rb
similarity index 63%
rename from spec/jobs/whats_app_adapter/three_sixty_dialog/upload_file_job_spec.rb
rename to spec/services/whats_app_adapter/three_sixty_dialog/upload_file_service_spec.rb
index c2894c0c4..3ba3d3d62 100644
--- a/spec/jobs/whats_app_adapter/three_sixty_dialog/upload_file_job_spec.rb
+++ b/spec/services/whats_app_adapter/three_sixty_dialog/upload_file_service_spec.rb
@@ -2,9 +2,9 @@
 
 require 'rails_helper'
 
-RSpec.describe WhatsAppAdapter::ThreeSixtyDialog::UploadFileJob do
-  describe '#perform_later(message_id:)' do
-    subject { -> { described_class.new.perform(message_id: message.id) } }
+RSpec.describe WhatsAppAdapter::ThreeSixtyDialog::UploadFileService do
+  describe '#call(request_id:)' do
+    subject { -> { described_class.call(request_id: message.request.id) } }
 
     let(:organization) { create(:organization, three_sixty_dialog_client_api_key: 'valid_api_key') }
     let(:message) { create(:message, request: create(:request, :with_file, organization: organization)) }
@@ -17,12 +17,7 @@
     end
 
     it 'schedules a job to send out the message with the file', vcr: { cassette_name: :three_sixty_dialog_upload_file_job } do
-      expect { subject.call }.to have_enqueued_job(
-        WhatsAppAdapter::ThreeSixtyDialogOutbound::File
-      ).with({
-               message_id: message.id,
-               file_id: external_file_id
-             })
+      expect { subject.call }.to (change { message.reload.request.external_file_ids }).from([]).to([external_file_id])
     end
   end
 end