From d017156f32e9a02a43f06d014df24d1025713606 Mon Sep 17 00:00:00 2001
From: Pranav <pranav@chatwoot.com>
Date: Wed, 5 Mar 2025 17:10:24 -0800
Subject: [PATCH 1/3] fix: Disable syncing IMAP if the account is suspended
 (#11031)

This PR disables the IMAP syncing if the account is suspended.
---
 Gemfile.lock                                  |  2 +-
 .../inboxes/fetch_imap_email_inboxes_job.rb   | 11 +++++--
 .../fetch_imap_email_inboxes_job_spec.rb      | 33 ++++++++++++++++---
 3 files changed, 39 insertions(+), 7 deletions(-)

diff --git a/Gemfile.lock b/Gemfile.lock
index 8591a0c34..857319fc4 100644
--- a/Gemfile.lock
+++ b/Gemfile.lock
@@ -561,7 +561,7 @@ GEM
       activesupport (>= 3.0.0)
     raabro (1.4.0)
     racc (1.8.1)
-    rack (2.2.11)
+    rack (2.2.12)
     rack-attack (6.7.0)
       rack (>= 1.0, < 4)
     rack-contrib (2.5.0)
diff --git a/app/jobs/inboxes/fetch_imap_email_inboxes_job.rb b/app/jobs/inboxes/fetch_imap_email_inboxes_job.rb
index b360940e3..56e8c2235 100644
--- a/app/jobs/inboxes/fetch_imap_email_inboxes_job.rb
+++ b/app/jobs/inboxes/fetch_imap_email_inboxes_job.rb
@@ -2,8 +2,15 @@ class Inboxes::FetchImapEmailInboxesJob < ApplicationJob
   queue_as :scheduled_jobs
 
   def perform
-    Inbox.where(channel_type: 'Channel::Email').all.find_each(batch_size: 100) do |inbox|
-      ::Inboxes::FetchImapEmailsJob.perform_later(inbox.channel) if inbox.channel.imap_enabled
+    email_inboxes = Inbox.where(channel_type: 'Channel::Email')
+    email_inboxes.find_each(batch_size: 100) do |inbox|
+      ::Inboxes::FetchImapEmailsJob.perform_later(inbox.channel) if should_fetch_emails?(inbox)
     end
   end
+
+  private
+
+  def should_fetch_emails?(inbox)
+    inbox.channel.imap_enabled && !inbox.account.suspended?
+  end
 end
diff --git a/spec/jobs/inboxes/fetch_imap_email_inboxes_job_spec.rb b/spec/jobs/inboxes/fetch_imap_email_inboxes_job_spec.rb
index ae4f540d4..18685a649 100644
--- a/spec/jobs/inboxes/fetch_imap_email_inboxes_job_spec.rb
+++ b/spec/jobs/inboxes/fetch_imap_email_inboxes_job_spec.rb
@@ -2,11 +2,19 @@ require 'rails_helper'
 
 RSpec.describe Inboxes::FetchImapEmailInboxesJob do
   let(:account) { create(:account) }
+  let(:suspended_account) { create(:account, status: 'suspended') }
+
   let(:imap_email_channel) do
-    create(:channel_email, imap_enabled: true, imap_address: 'imap.gmail.com', imap_port: 993, imap_login: 'imap@gmail.com',
-                           imap_password: 'password', account: account)
+    create(:channel_email, imap_enabled: true, account: account)
+  end
+
+  let(:imap_email_channel_suspended) do
+    create(:channel_email, imap_enabled: true, account: suspended_account)
+  end
+
+  let(:disabled_imap_channel) do
+    create(:channel_email, imap_enabled: false, account: account)
   end
-  let(:email_inbox) { create(:inbox, channel: imap_email_channel, account: account) }
 
   it 'enqueues the job' do
     expect { described_class.perform_later }.to have_enqueued_job(described_class)
@@ -14,9 +22,26 @@ RSpec.describe Inboxes::FetchImapEmailInboxesJob do
   end
 
   context 'when called' do
-    it 'fetch all the email channels' do
+    it 'fetches emails only for active accounts with imap enabled' do
+      # Should call perform_later only once for the active, imap-enabled inbox
       expect(Inboxes::FetchImapEmailsJob).to receive(:perform_later).with(imap_email_channel).once
 
+      # Should not call for suspended account or disabled IMAP channels
+      expect(Inboxes::FetchImapEmailsJob).not_to receive(:perform_later).with(imap_email_channel_suspended)
+      expect(Inboxes::FetchImapEmailsJob).not_to receive(:perform_later).with(disabled_imap_channel)
+
+      described_class.perform_now
+    end
+
+    it 'skips suspended accounts' do
+      expect(Inboxes::FetchImapEmailsJob).not_to receive(:perform_later).with(imap_email_channel_suspended)
+
+      described_class.perform_now
+    end
+
+    it 'skips disabled imap channels' do
+      expect(Inboxes::FetchImapEmailsJob).not_to receive(:perform_later).with(disabled_imap_channel)
+
       described_class.perform_now
     end
   end

From 7e1458fd32f8c24e4da84097f6510b120e22907b Mon Sep 17 00:00:00 2001
From: Sivin Varghese <64252451+iamsivin@users.noreply.github.com>
Date: Thu, 6 Mar 2025 10:53:02 +0530
Subject: [PATCH 2/3] fix: Issue when saving hotkeys (#11026)

# Pull Request Template

## Description

This PR fixes an issue when saving send message button hotkeys, where a
TypeError occurs: `this.updateUISettings is not a function`.

This issue arises after merging this PR
https://github.com/chatwoot/chatwoot/pull/10974

Fixes
https://chatwoot-p3.sentry.io/issues/6339976939/events/ca9946f92cb74428a72f1f74976a56a3/

## Type of change

- [x] Bug fix (non-breaking change which fixes an issue)

## Checklist:

- [x] My code follows the style guidelines of this project
- [x] I have performed a self-review of my code
- [ ] I have commented on my code, particularly in hard-to-understand
areas
- [ ] I have made corresponding changes to the documentation
- [x] My changes generate no new warnings
- [ ] I have added tests that prove my fix is effective or that my
feature works
- [x] New and existing unit tests pass locally with my changes
- [ ] Any dependent changes have been merged and published in downstream
modules
---
 .../dashboard/routes/dashboard/settings/profile/Index.vue      | 3 ++-
 1 file changed, 2 insertions(+), 1 deletion(-)

diff --git a/app/javascript/dashboard/routes/dashboard/settings/profile/Index.vue b/app/javascript/dashboard/routes/dashboard/settings/profile/Index.vue
index 85204627a..45a060e05 100644
--- a/app/javascript/dashboard/routes/dashboard/settings/profile/Index.vue
+++ b/app/javascript/dashboard/routes/dashboard/settings/profile/Index.vue
@@ -39,13 +39,14 @@ export default {
   },
   mixins: [globalConfigMixin],
   setup() {
-    const { isEditorHotKeyEnabled } = useUISettings();
+    const { isEditorHotKeyEnabled, updateUISettings } = useUISettings();
     const { currentFontSize, updateFontSize } = useFontSize();
 
     return {
       currentFontSize,
       updateFontSize,
       isEditorHotKeyEnabled,
+      updateUISettings,
     };
   },
   data() {

From 8d85a02ca9a7a4f81fb58e987758103219642801 Mon Sep 17 00:00:00 2001
From: Shivam Mishra <scm.mymail@gmail.com>
Date: Thu, 6 Mar 2025 20:09:47 +0530
Subject: [PATCH 3/3] feat: handle Channel errors (#11015)

This PR adds missing error handlers for the following channels and cases

1. WhatsApp - Generic Handlers for both Cloud and 360Dialog (Deprecated)
2. Instagram - Handler for a case where there is an HTTP error instead
of an `:error` in the 200 response
3. Facebook - Errors from the two sentry issues
([Net::OpenTimeout](https://chatwoot-p3.sentry.io/issues/6164805227) &
[JSON::ParserError](https://chatwoot-p3.sentry.io/issues/5903200786))
4. SMS: Generic handlers for Bandwidth SMS

#### Checklist

- [x] Bandwidth SMS
- [x] Whatsapp Cloud + 360 Dialog
- [x] Twilio SMS
- [x] Line
- [x] Telegram
- [x] Instagram
- [x] Facebook
- [x] GMail
- [x] 365 Mail
- [x] SMTP Mail

---------

Co-authored-by: Muhsin Keloth <muhsinkeramam@gmail.com>
---
 .../components-next/message/MessageError.vue  |   2 +-
 .../components-next/message/MessageMeta.vue   |   1 +
 app/models/channel/sms.rb                     |  21 +++-
 .../facebook/send_on_facebook_service.rb      |  21 +++-
 .../instagram/send_on_instagram_service.rb    |  28 +++--
 .../whatsapp/providers/base_service.rb        |  27 ++++
 .../providers/whatsapp_360_dialog_service.rb  |  12 +-
 .../providers/whatsapp_cloud_service.rb       |  12 +-
 .../facebook/send_on_facebook_service_spec.rb |  49 ++++++++
 .../send_on_instagram_service_spec.rb         | 108 +++++++++++-----
 .../providers/whatsapp_cloud_service_spec.rb  |  52 ++++++++
 .../whatsapp/send_on_whatsapp_service_spec.rb | 115 +++++++++---------
 12 files changed, 324 insertions(+), 124 deletions(-)

diff --git a/app/javascript/dashboard/components-next/message/MessageError.vue b/app/javascript/dashboard/components-next/message/MessageError.vue
index e113ada71..d3a03e746 100644
--- a/app/javascript/dashboard/components-next/message/MessageError.vue
+++ b/app/javascript/dashboard/components-next/message/MessageError.vue
@@ -26,7 +26,7 @@ const { t } = useI18n();
         />
       </div>
       <div
-        class="absolute bg-n-alpha-3 px-4 py-3 border rounded-xl border-n-strong text-n-slate-12 bottom-6 w-52 text-xs backdrop-blur-[100px] shadow-[0px_0px_24px_0px_rgba(0,0,0,0.12)] opacity-0 invisible group-hover:opacity-100 group-hover:visible transition-all"
+        class="absolute bg-n-alpha-3 px-4 py-3 border rounded-xl border-n-strong text-n-slate-12 bottom-6 w-52 text-xs backdrop-blur-[100px] shadow-[0px_0px_24px_0px_rgba(0,0,0,0.12)] opacity-0 invisible group-hover:opacity-100 group-hover:visible transition-all break-all"
         :class="{
           'ltr:left-0 rtl:right-0': orientation === ORIENTATION.LEFT,
           'ltr:right-0 rtl:left-0': orientation === ORIENTATION.RIGHT,
diff --git a/app/javascript/dashboard/components-next/message/MessageMeta.vue b/app/javascript/dashboard/components-next/message/MessageMeta.vue
index 3b276221b..41a0a3d15 100644
--- a/app/javascript/dashboard/components-next/message/MessageMeta.vue
+++ b/app/javascript/dashboard/components-next/message/MessageMeta.vue
@@ -102,6 +102,7 @@ const statusToShow = computed(() => {
   if (isRead.value) return MESSAGE_STATUS.READ;
   if (isDelivered.value) return MESSAGE_STATUS.DELIVERED;
   if (isSent.value) return MESSAGE_STATUS.SENT;
+  if (status.value === MESSAGE_STATUS.FAILED) return MESSAGE_STATUS.FAILED;
 
   return MESSAGE_STATUS.PROGRESS;
 });
diff --git a/app/models/channel/sms.rb b/app/models/channel/sms.rb
index e6f993e59..ab04f55f0 100644
--- a/app/models/channel/sms.rb
+++ b/app/models/channel/sms.rb
@@ -37,7 +37,7 @@ class Channel::Sms < ApplicationRecord
     body = message_body(contact_number, message.content)
     body['media'] = message.attachments.map(&:download_url) if message.attachments.present?
 
-    send_to_bandwidth(body)
+    send_to_bandwidth(body, message)
   end
 
   def send_text_message(contact_number, message_content)
@@ -56,7 +56,7 @@ class Channel::Sms < ApplicationRecord
     }
   end
 
-  def send_to_bandwidth(body)
+  def send_to_bandwidth(body, message = nil)
     response = HTTParty.post(
       "#{api_base_path}/users/#{provider_config['account_id']}/messages",
       basic_auth: bandwidth_auth,
@@ -64,7 +64,22 @@ class Channel::Sms < ApplicationRecord
       body: body.to_json
     )
 
-    response.success? ? response.parsed_response['id'] : nil
+    if response.success?
+      response.parsed_response['id']
+    else
+      handle_error(response, message)
+      nil
+    end
+  end
+
+  def handle_error(response, message)
+    Rails.logger.error("[#{account_id}] Error sending SMS: #{response.parsed_response['description']}")
+    return if message.blank?
+
+    # https://dev.bandwidth.com/apis/messaging-apis/messaging/#tag/Messages/operation/createMessage
+    message.external_error = response.parsed_response['description']
+    message.status = :failed
+    message.save!
   end
 
   def bandwidth_auth
diff --git a/app/services/facebook/send_on_facebook_service.rb b/app/services/facebook/send_on_facebook_service.rb
index 514ba3e1f..5dde19c5a 100644
--- a/app/services/facebook/send_on_facebook_service.rb
+++ b/app/services/facebook/send_on_facebook_service.rb
@@ -20,15 +20,30 @@ class Facebook::SendOnFacebookService < Base::SendOnChannelService
   end
 
   def send_message_to_facebook(delivery_params)
-    result = Facebook::Messenger::Bot.deliver(delivery_params, page_id: channel.page_id)
-    parsed_result = JSON.parse(result)
+    parsed_result = deliver_message(delivery_params)
+    return if parsed_result.nil?
+
     if parsed_result['error'].present?
       message.update!(status: :failed, external_error: external_error(parsed_result))
-      Rails.logger.info "Facebook::SendOnFacebookService: Error sending message to Facebook : Page - #{channel.page_id} : #{result}"
+      Rails.logger.info "Facebook::SendOnFacebookService: Error sending message to Facebook : Page - #{channel.page_id} : #{parsed_result}"
     end
+
     message.update!(source_id: parsed_result['message_id']) if parsed_result['message_id'].present?
   end
 
+  def deliver_message(delivery_params)
+    result = Facebook::Messenger::Bot.deliver(delivery_params, page_id: channel.page_id)
+    JSON.parse(result)
+  rescue JSON::ParserError
+    message.update!(status: :failed, external_error: 'Facebook was unable to process this request')
+    Rails.logger.error "Facebook::SendOnFacebookService: Error parsing JSON response from Facebook : Page - #{channel.page_id} : #{result}"
+    nil
+  rescue Net::OpenTimeout
+    message.update!(status: :failed, external_error: 'Request timed out, please try again later')
+    Rails.logger.error "Facebook::SendOnFacebookService: Timeout error sending message to Facebook : Page - #{channel.page_id}"
+    nil
+  end
+
   def fb_text_message_params
     {
       recipient: { id: contact.get_source_id(inbox.id) },
diff --git a/app/services/instagram/send_on_instagram_service.rb b/app/services/instagram/send_on_instagram_service.rb
index a681745d8..23cd04370 100644
--- a/app/services/instagram/send_on_instagram_service.rb
+++ b/app/services/instagram/send_on_instagram_service.rb
@@ -70,22 +70,28 @@ class Instagram::SendOnInstagramService < Base::SendOnChannelService
       query: query
     )
 
-    if response[:error].present?
-      Rails.logger.error("Instagram response: #{response['error']} : #{message_content}")
-      message.status = :failed
-      message.external_error = external_error(response)
+    handle_response(response, message_content)
+  end
+
+  def handle_response(response, message_content)
+    parsed_response = response.parsed_response
+    if response.success? && parsed_response['error'].blank?
+      message.update!(source_id: parsed_response['message_id'])
+
+      parsed_response
+    else
+      external_error = external_error(parsed_response)
+      Rails.logger.error("Instagram response: #{external_error} : #{message_content}")
+      message.update!(status: :failed, external_error: external_error)
+
+      nil
     end
-
-    message.source_id = response['message_id'] if response['message_id'].present?
-    message.save!
-
-    response
   end
 
   def external_error(response)
     # https://developers.facebook.com/docs/instagram-api/reference/error-codes/
-    error_message = response[:error][:message]
-    error_code = response[:error][:code]
+    error_message = response.dig('error', 'message')
+    error_code = response.dig('error', 'code')
 
     "#{error_code} - #{error_message}"
   end
diff --git a/app/services/whatsapp/providers/base_service.rb b/app/services/whatsapp/providers/base_service.rb
index 9923017dd..55714ba4d 100644
--- a/app/services/whatsapp/providers/base_service.rb
+++ b/app/services/whatsapp/providers/base_service.rb
@@ -27,6 +27,33 @@ class Whatsapp::Providers::BaseService
     raise 'Overwrite this method in child class'
   end
 
+  def error_message
+    raise 'Overwrite this method in child class'
+  end
+
+  def process_response(response)
+    parsed_response = response.parsed_response
+    if response.success? && parsed_response['error'].blank?
+      parsed_response['messages'].first['id']
+    else
+      handle_error(response)
+      nil
+    end
+  end
+
+  def handle_error(response)
+    Rails.logger.error response.body
+    return if @message.blank?
+
+    # https://developers.facebook.com/docs/whatsapp/cloud-api/support/error-codes/#sample-response
+    error_message = error_message(response)
+    return if error_message.blank?
+
+    @message.external_error = error_message
+    @message.status = :failed
+    @message.save!
+  end
+
   def create_buttons(items)
     buttons = []
     items.each do |item|
diff --git a/app/services/whatsapp/providers/whatsapp_360_dialog_service.rb b/app/services/whatsapp/providers/whatsapp_360_dialog_service.rb
index 668162905..61cdeebf1 100644
--- a/app/services/whatsapp/providers/whatsapp_360_dialog_service.rb
+++ b/app/services/whatsapp/providers/whatsapp_360_dialog_service.rb
@@ -1,5 +1,6 @@
 class Whatsapp::Providers::Whatsapp360DialogService < Whatsapp::Providers::BaseService
   def send_message(phone_number, message)
+    @message = message
     if message.attachments.present?
       send_attachment_message(phone_number, message)
     elsif message.content_type == 'input_select'
@@ -78,6 +79,7 @@ class Whatsapp::Providers::Whatsapp360DialogService < Whatsapp::Providers::BaseS
     }
     type_content['caption'] = message.content unless %w[audio sticker].include?(type)
     type_content['filename'] = attachment.file.filename if type == 'document'
+
     response = HTTParty.post(
       "#{api_base_path}/messages",
       headers: api_headers,
@@ -91,13 +93,9 @@ class Whatsapp::Providers::Whatsapp360DialogService < Whatsapp::Providers::BaseS
     process_response(response)
   end
 
-  def process_response(response)
-    if response.success?
-      response['messages'].first['id']
-    else
-      Rails.logger.error response.body
-      nil
-    end
+  def error_message(response)
+    # {"meta": {"success": false, "http_code": 400, "developer_message": "errro-message", "360dialog_trace_id": "someid"}}
+    response.parsed_response.dig('meta', 'developer_message')
   end
 
   def template_body_parameters(template_info)
diff --git a/app/services/whatsapp/providers/whatsapp_cloud_service.rb b/app/services/whatsapp/providers/whatsapp_cloud_service.rb
index f1af38e36..ec2275920 100644
--- a/app/services/whatsapp/providers/whatsapp_cloud_service.rb
+++ b/app/services/whatsapp/providers/whatsapp_cloud_service.rb
@@ -1,5 +1,7 @@
 class Whatsapp::Providers::WhatsappCloudService < Whatsapp::Providers::BaseService
   def send_message(phone_number, message)
+    @message = message
+
     if message.attachments.present?
       send_attachment_message(phone_number, message)
     elsif message.content_type == 'input_select'
@@ -111,13 +113,9 @@ class Whatsapp::Providers::WhatsappCloudService < Whatsapp::Providers::BaseServi
     process_response(response)
   end
 
-  def process_response(response)
-    if response.success?
-      response['messages'].first['id']
-    else
-      Rails.logger.error response.body
-      nil
-    end
+  def error_message(response)
+    # https://developers.facebook.com/docs/whatsapp/cloud-api/support/error-codes/#sample-response
+    response.parsed_response&.dig('error', 'message')
   end
 
   def template_body_parameters(template_info)
diff --git a/spec/services/facebook/send_on_facebook_service_spec.rb b/spec/services/facebook/send_on_facebook_service_spec.rb
index 2fcea8b72..cddf527cb 100644
--- a/spec/services/facebook/send_on_facebook_service_spec.rb
+++ b/spec/services/facebook/send_on_facebook_service_spec.rb
@@ -117,5 +117,54 @@ describe Facebook::SendOnFacebookService do
         expect(message.reload.status).to eq('failed')
       end
     end
+
+    context 'when deliver_message fails' do
+      let(:message) { create(:message, message_type: 'outgoing', inbox: facebook_inbox, account: account, conversation: conversation) }
+
+      it 'handles JSON parse errors' do
+        allow(bot).to receive(:deliver).and_return('invalid_json')
+        described_class.new(message: message).perform
+
+        expect(message.reload.status).to eq('failed')
+        expect(message.external_error).to eq('Facebook was unable to process this request')
+      end
+
+      it 'handles timeout errors' do
+        allow(bot).to receive(:deliver).and_raise(Net::OpenTimeout)
+        described_class.new(message: message).perform
+
+        expect(message.reload.status).to eq('failed')
+        expect(message.external_error).to eq('Request timed out, please try again later')
+      end
+
+      it 'handles facebook error with code' do
+        error_response = {
+          error: {
+            message: 'Invalid OAuth access token.',
+            type: 'OAuthException',
+            code: 190,
+            fbtrace_id: 'BLBz/WZt8dN'
+          }
+        }.to_json
+        allow(bot).to receive(:deliver).and_return(error_response)
+
+        described_class.new(message: message).perform
+
+        expect(message.reload.status).to eq('failed')
+        expect(message.external_error).to eq('190 - Invalid OAuth access token.')
+      end
+
+      it 'handles successful delivery with message_id' do
+        success_response = {
+          message_id: 'mid.1456970487936:c34767dfe57ee6e339'
+        }.to_json
+        allow(bot).to receive(:deliver).and_return(success_response)
+
+        described_class.new(message: message).perform
+
+        expect(message.reload.source_id).to eq('mid.1456970487936:c34767dfe57ee6e339')
+        expect(message.status).not_to eq('failed')
+      end
+    end
   end
 end
diff --git a/spec/services/instagram/send_on_instagram_service_spec.rb b/spec/services/instagram/send_on_instagram_service_spec.rb
index 8900171f3..3e88b1cdd 100644
--- a/spec/services/instagram/send_on_instagram_service_spec.rb
+++ b/spec/services/instagram/send_on_instagram_service_spec.rb
@@ -4,7 +4,7 @@ describe Instagram::SendOnInstagramService do
   subject(:send_reply_service) { described_class.new(message: message) }
 
   before do
-    stub_request(:post, /graph.facebook.com/)
+    stub_request(:post, /graph\.facebook\.com/)
     create(:message, message_type: :incoming, inbox: instagram_inbox, account: account, conversation: conversation)
   end
 
@@ -15,16 +15,49 @@ describe Instagram::SendOnInstagramService do
   let(:contact_inbox) { create(:contact_inbox, contact: contact, inbox: instagram_inbox) }
   let(:conversation) { create(:conversation, contact: contact, inbox: instagram_inbox, contact_inbox: contact_inbox) }
   let(:response) { double }
+  let(:mock_response) do
+    instance_double(
+      HTTParty::Response,
+      :success? => true,
+      :body => { message_id: 'anyrandommessageid1234567890' }.to_json,
+      :parsed_response => { 'message_id' => 'anyrandommessageid1234567890' }
+    )
+  end
+
+  let(:error_body) do
+    {
+      'error' => {
+        'message' => 'The Instagram account is restricted.',
+        'type' => 'OAuthException',
+        'code' => 400,
+        'fbtrace_id' => 'anyrandomfbtraceid1234567890'
+      }
+    }
+  end
+
+  let(:error_response) do
+    instance_double(
+      HTTParty::Response,
+      :success? => false,
+      :body => error_body.to_json,
+      :parsed_response => error_body
+    )
+  end
+
+  let(:response_with_error) do
+    instance_double(
+      HTTParty::Response,
+      :success? => true,
+      :body => error_body.to_json,
+      :parsed_response => error_body
+    )
+  end
 
   describe '#perform' do
     context 'with reply' do
       before do
         allow(Facebook::Messenger::Configuration::AppSecretProofCalculator).to receive(:call).and_return('app_secret_key', 'access_token')
-        allow(HTTParty).to receive(:post).and_return(
-          {
-            'message_id': 'anyrandommessageid1234567890'
-          }
-        )
+        allow(HTTParty).to receive(:post).and_return(mock_response)
       end
 
       context 'without message_tag HUMAN_AGENT' do
@@ -35,22 +68,8 @@ describe Instagram::SendOnInstagramService do
         it 'if message is sent from chatwoot and is outgoing' do
           message = create(:message, message_type: 'outgoing', inbox: instagram_inbox, account: account, conversation: conversation)
 
-          allow(HTTParty).to receive(:post).with(
-            {
-              recipient: { id: contact.get_source_id(instagram_inbox.id) },
-              message: {
-                text: message.content
-              }
-            }
-          ).and_return(
-            {
-              'message_id': 'anyrandommessageid1234567890'
-            }
-          )
-
           response = described_class.new(message: message).perform
-
-          expect(response).to eq({ message_id: 'anyrandommessageid1234567890' })
+          expect(response['message_id']).to eq('anyrandommessageid1234567890')
         end
 
         it 'if message is sent from chatwoot and is outgoing with multiple attachments' do
@@ -78,22 +97,13 @@ describe Instagram::SendOnInstagramService do
           message.save!
           response = described_class.new(message: message).perform
 
-          expect(response).to eq({ message_id: 'anyrandommessageid1234567890' })
+          expect(response['message_id']).to eq('anyrandommessageid1234567890')
         end
 
         it 'if message sent from chatwoot is failed' do
           message = create(:message, message_type: 'outgoing', inbox: instagram_inbox, account: account, conversation: conversation)
 
-          allow(HTTParty).to receive(:post).and_return(
-            {
-              'error': {
-                'message': 'The Instagram account is restricted.',
-                'type': 'OAuthException',
-                'code': 400,
-                'fbtrace_id': 'anyrandomfbtraceid1234567890'
-              }
-            }
-          )
+          allow(HTTParty).to receive(:post).and_return(response_with_error)
           described_class.new(message: message).perform
           expect(HTTParty).to have_received(:post)
           expect(message.reload.status).to eq('failed')
@@ -129,5 +139,39 @@ describe Instagram::SendOnInstagramService do
         end
       end
     end
+
+    context 'when handling errors' do
+      before do
+        allow(Facebook::Messenger::Configuration::AppSecretProofCalculator).to receive(:call).and_return('app_secret_key', 'access_token')
+      end
+
+      it 'handles HTTP errors' do
+        message = create(:message, message_type: 'outgoing', inbox: instagram_inbox, account: account, conversation: conversation)
+        allow(HTTParty).to receive(:post).and_return(error_response)
+
+        described_class.new(message: message).perform
+
+        expect(message.reload.status).to eq('failed')
+        expect(message.reload.external_error).to eq('400 - The Instagram account is restricted.')
+      end
+
+      it 'handles response errors' do
+        message = create(:message, message_type: 'outgoing', inbox: instagram_inbox, account: account, conversation: conversation)
+
+        error_response = instance_double(
+          HTTParty::Response,
+          success?: true,
+          body: { 'error' => { 'message' => 'Invalid message format', 'code' => 100 } }.to_json,
+          parsed_response: { 'error' => { 'message' => 'Invalid message format', 'code' => 100 } }
+        )
+
+        allow(HTTParty).to receive(:post).and_return(error_response)
+
+        described_class.new(message: message).perform
+
+        expect(message.reload.status).to eq('failed')
+        expect(message.reload.external_error).to eq('100 - Invalid message format')
+      end
+    end
   end
 end
diff --git a/spec/services/whatsapp/providers/whatsapp_cloud_service_spec.rb b/spec/services/whatsapp/providers/whatsapp_cloud_service_spec.rb
index 7c2b79b8d..134d69fee 100644
--- a/spec/services/whatsapp/providers/whatsapp_cloud_service_spec.rb
+++ b/spec/services/whatsapp/providers/whatsapp_cloud_service_spec.rb
@@ -263,4 +263,56 @@ describe Whatsapp::Providers::WhatsappCloudService do
       end
     end
   end
+
+  describe '#handle_error' do
+    let(:error_message) { 'Invalid message format' }
+    let(:error_response) do
+      {
+        'error' => {
+          'message' => error_message,
+          'code' => 100
+        }
+      }
+    end
+
+    let(:error_response_object) do
+      instance_double(
+        HTTParty::Response,
+        body: error_response.to_json,
+        parsed_response: error_response
+      )
+    end
+
+    before do
+      allow(Rails.logger).to receive(:error)
+    end
+
+    context 'when there is a message' do
+      it 'logs error and updates message status' do
+        service.instance_variable_set(:@message, message)
+        service.send(:handle_error, error_response_object)
+
+        expect(message.reload.status).to eq('failed')
+        expect(message.reload.external_error).to eq(error_message)
+      end
+    end
+
+    context 'when error message is blank' do
+      let(:error_response_object) do
+        instance_double(
+          HTTParty::Response,
+          body: '{}',
+          parsed_response: {}
+        )
+      end
+
+      it 'logs error but does not update message' do
+        service.instance_variable_set(:@message, message)
+        service.send(:handle_error, error_response_object)
+
+        expect(message.reload.status).not_to eq('failed')
+        expect(message.reload.external_error).to be_nil
+      end
+    end
+  end
 end
diff --git a/spec/services/whatsapp/send_on_whatsapp_service_spec.rb b/spec/services/whatsapp/send_on_whatsapp_service_spec.rb
index 0df9316f5..88f3f7740 100644
--- a/spec/services/whatsapp/send_on_whatsapp_service_spec.rb
+++ b/spec/services/whatsapp/send_on_whatsapp_service_spec.rb
@@ -12,13 +12,30 @@ describe Whatsapp::SendOnWhatsappService do
   describe '#perform' do
     before do
       stub_request(:post, 'https://waba.360dialog.io/v1/configs/webhook')
+      stub_request(:post, 'https://waba.360dialog.io/v1/messages')
     end
 
     context 'when a valid message' do
-      let(:whatsapp_request) { double }
+      let(:whatsapp_request) { instance_double(HTTParty::Response) }
       let!(:whatsapp_channel) { create(:channel_whatsapp, sync_templates: false) }
       let!(:contact_inbox) { create(:contact_inbox, inbox: whatsapp_channel.inbox, source_id: '123456789') }
       let!(:conversation) { create(:conversation, contact_inbox: contact_inbox, inbox: whatsapp_channel.inbox) }
+      let(:api_key) { 'test_key' }
+      let(:headers) { { 'D360-API-KEY' => api_key, 'Content-Type' => 'application/json' } }
+      let(:template_body) do
+        {
+          to: '123456789',
+          template: {
+            name: 'sample_shipping_confirmation',
+            namespace: '23423423_2342423_324234234_2343224',
+            language: { 'policy': 'deterministic', 'code': 'en_US' },
+            components: [{ 'type': 'body', 'parameters': [{ 'type': 'text', 'text': '3' }] }]
+          },
+          type: 'template'
+        }
+      end
+
+      let(:success_response) { { 'messages' => [{ 'id' => '123456789' }] }.to_json }
 
       it 'calls channel.send_message when with in 24 hour limit' do
         # to handle the case of 24 hour window limit.
@@ -26,14 +43,14 @@ describe Whatsapp::SendOnWhatsappService do
                          conversation: conversation)
         message = create(:message, message_type: :outgoing, content: 'test',
                                    conversation: conversation)
-        allow(HTTParty).to receive(:post).and_return(whatsapp_request)
-        allow(whatsapp_request).to receive(:success?).and_return(true)
-        allow(whatsapp_request).to receive(:[]).with('messages').and_return([{ 'id' => '123456789' }])
-        expect(HTTParty).to receive(:post).with(
-          'https://waba.360dialog.io/v1/messages',
-          headers: { 'D360-API-KEY' => 'test_key', 'Content-Type' => 'application/json' },
-          body: { 'to' => '123456789', 'text' => { 'body' => 'test' }, 'type' => 'text' }.to_json
-        )
+
+        stub_request(:post, 'https://waba.360dialog.io/v1/messages')
+          .with(
+            headers: headers,
+            body: { 'to' => '123456789', 'text' => { 'body' => 'test' }, 'type' => 'text' }.to_json
+          )
+          .to_return(status: 200, body: success_response, headers: { 'content-type' => 'application/json' })
+
         described_class.new(message: message).perform
         expect(message.reload.source_id).to eq('123456789')
       end
@@ -41,23 +58,13 @@ describe Whatsapp::SendOnWhatsappService do
       it 'calls channel.send_template when after 24 hour limit' do
         message = create(:message, message_type: :outgoing, content: 'Your package has been shipped. It will be delivered in 3 business days.',
                                    conversation: conversation)
-        allow(HTTParty).to receive(:post).and_return(whatsapp_request)
-        allow(whatsapp_request).to receive(:success?).and_return(true)
-        allow(whatsapp_request).to receive(:[]).with('messages').and_return([{ 'id' => '123456789' }])
-        expect(HTTParty).to receive(:post).with(
-          'https://waba.360dialog.io/v1/messages',
-          headers: { 'D360-API-KEY' => 'test_key', 'Content-Type' => 'application/json' },
-          body: {
-            to: '123456789',
-            template: {
-              name: 'sample_shipping_confirmation',
-              namespace: '23423423_2342423_324234234_2343224',
-              language: { 'policy': 'deterministic', 'code': 'en_US' },
-              components: [{ 'type': 'body', 'parameters': [{ 'type': 'text', 'text': '3' }] }]
-            },
-            type: 'template'
-          }.to_json
-        )
+
+        stub_request(:post, 'https://waba.360dialog.io/v1/messages')
+          .with(
+            headers: headers,
+            body: template_body.to_json
+          ).to_return(status: 200, body: success_response, headers: { 'content-type' => 'application/json' })
+
         described_class.new(message: message).perform
         expect(message.reload.source_id).to eq('123456789')
       end
@@ -65,23 +72,12 @@ describe Whatsapp::SendOnWhatsappService do
       it 'calls channel.send_template if template_params are present' do
         message = create(:message, additional_attributes: { template_params: template_params },
                                    content: 'Your package will be delivered in 3 business days.', conversation: conversation, message_type: :outgoing)
-        allow(HTTParty).to receive(:post).and_return(whatsapp_request)
-        allow(whatsapp_request).to receive(:success?).and_return(true)
-        allow(whatsapp_request).to receive(:[]).with('messages').and_return([{ 'id' => '123456789' }])
-        expect(HTTParty).to receive(:post).with(
-          'https://waba.360dialog.io/v1/messages',
-          headers: { 'D360-API-KEY' => 'test_key', 'Content-Type' => 'application/json' },
-          body: {
-            to: '123456789',
-            template: {
-              name: 'sample_shipping_confirmation',
-              namespace: '23423423_2342423_324234234_2343224',
-              language: { 'policy': 'deterministic', 'code': 'en_US' },
-              components: [{ 'type': 'body', 'parameters': [{ 'type': 'text', 'text': '3' }] }]
-            },
-            type: 'template'
-          }.to_json
-        )
+        stub_request(:post, 'https://waba.360dialog.io/v1/messages')
+          .with(
+            headers: headers,
+            body: template_body.to_json
+          ).to_return(status: 200, body: success_response, headers: { 'content-type' => 'application/json' })
+
         described_class.new(message: message).perform
         expect(message.reload.source_id).to eq('123456789')
       end
@@ -93,23 +89,22 @@ describe Whatsapp::SendOnWhatsappService do
           content: 'عميلنا العزيز الرجاء الرد على هذه الرسالة بكلمة *نعم* للرد على إستفساركم من قبل خدمة العملاء.',
           conversation: conversation
         )
-        allow(HTTParty).to receive(:post).and_return(whatsapp_request)
-        allow(whatsapp_request).to receive(:success?).and_return(true)
-        allow(whatsapp_request).to receive(:[]).with('messages').and_return([{ 'id' => '123456789' }])
-        expect(HTTParty).to receive(:post).with(
-          'https://waba.360dialog.io/v1/messages',
-          headers: { 'D360-API-KEY' => 'test_key', 'Content-Type' => 'application/json' },
-          body: {
-            to: '123456789',
-            template: {
-              name: 'customer_yes_no',
-              namespace: '2342384942_32423423_23423fdsdaf23',
-              language: { 'policy': 'deterministic', 'code': 'ar' },
-              components: [{ 'type': 'body', 'parameters': [] }]
-            },
-            type: 'template'
-          }.to_json
-        )
+
+        stub_request(:post, 'https://waba.360dialog.io/v1/messages')
+          .with(
+            headers: headers,
+            body: {
+              to: '123456789',
+              template: {
+                name: 'customer_yes_no',
+                namespace: '2342384942_32423423_23423fdsdaf23',
+                language: { 'policy': 'deterministic', 'code': 'ar' },
+                components: [{ 'type': 'body', 'parameters': [] }]
+              },
+              type: 'template'
+            }.to_json
+          ).to_return(status: 200, body: success_response, headers: { 'content-type' => 'application/json' })
+
         described_class.new(message: message).perform
         expect(message.reload.source_id).to eq('123456789')
       end