diff --git a/app/javascript/dashboard/components/widgets/conversation/ReplyBox.vue b/app/javascript/dashboard/components/widgets/conversation/ReplyBox.vue
index 5ad5f66a4..23f339f46 100644
--- a/app/javascript/dashboard/components/widgets/conversation/ReplyBox.vue
+++ b/app/javascript/dashboard/components/widgets/conversation/ReplyBox.vue
@@ -964,6 +964,19 @@ export default {
         (item, index) => itemIndex !== index
       );
     },
+    setReplyToInPayload(payload) {
+      if (this.inReplyTo?.id) {
+        return {
+          ...payload,
+          contentAttributes: {
+            ...payload.contentAttributes,
+            in_reply_to: this.inReplyTo.id,
+          },
+        };
+      }
+
+      return payload;
+    },
     getMessagePayloadForWhatsapp(message) {
       const multipleMessagePayload = [];
 
@@ -973,41 +986,41 @@ export default {
           const attachedFile = this.globalConfig.directUploadsEnabled
             ? attachment.blobSignedId
             : attachment.resource.file;
-          const attachmentPayload = {
+          let attachmentPayload = {
             conversationId: this.currentChat.id,
             files: [attachedFile],
             private: false,
             message: caption,
             sender: this.sender,
           };
+
+          attachmentPayload = this.setReplyToInPayload(attachmentPayload);
           multipleMessagePayload.push(attachmentPayload);
           caption = '';
         });
       } else {
-        const messagePayload = {
+        let messagePayload = {
           conversationId: this.currentChat.id,
           message,
           private: false,
           sender: this.sender,
         };
+
+        messagePayload = this.setReplyToInPayload(messagePayload);
+
         multipleMessagePayload.push(messagePayload);
       }
 
       return multipleMessagePayload;
     },
     getMessagePayload(message) {
-      const messagePayload = {
+      let messagePayload = {
         conversationId: this.currentChat.id,
         message,
         private: this.isPrivate,
         sender: this.sender,
       };
-
-      if (this.inReplyTo?.id) {
-        messagePayload.contentAttributes = {
-          in_reply_to: this.inReplyTo.id,
-        };
-      }
+      messagePayload = this.setReplyToInPayload(messagePayload);
 
       if (this.attachedFiles && this.attachedFiles.length) {
         messagePayload.files = [];
diff --git a/app/javascript/dashboard/components/widgets/conversation/bubble/ReplyTo.vue b/app/javascript/dashboard/components/widgets/conversation/bubble/ReplyTo.vue
index 06b6f0445..fb557293b 100644
--- a/app/javascript/dashboard/components/widgets/conversation/bubble/ReplyTo.vue
+++ b/app/javascript/dashboard/components/widgets/conversation/bubble/ReplyTo.vue
@@ -1,10 +1,11 @@
 <template>
   <div
-    class="px-2 py-1.5 -mx-2 rounded-sm min-w-[15rem] mb-2"
+    class="px-2 py-1.5 rounded-sm min-w-[10rem] mb-2"
     :class="{
       'bg-slate-100 dark:bg-slate-600 dark:text-slate-50':
         messageType === MESSAGE_TYPE.INCOMING,
       'bg-woot-600 text-woot-50': messageType === MESSAGE_TYPE.OUTGOING,
+      '-mx-2': message.content,
     }"
   >
     <message-preview
diff --git a/app/models/message.rb b/app/models/message.rb
index 702c1193e..93258da5a 100644
--- a/app/models/message.rb
+++ b/app/models/message.rb
@@ -239,13 +239,11 @@ class Message < ApplicationRecord
     in_reply_to = content_attributes[:in_reply_to]
     in_reply_to_external_id = content_attributes[:in_reply_to_external_id]
 
-    if in_reply_to.present? && in_reply_to_external_id.blank?
-      message = conversation.messages.find_by(id: in_reply_to)
-      content_attributes[:in_reply_to_external_id] = message.try(:source_id)
-    elsif in_reply_to_external_id.present? && in_reply_to.blank?
-      message = conversation.messages.find_by(source_id: in_reply_to_external_id)
-      content_attributes[:in_reply_to] = message.try(:id)
-    end
+    Messages::InReplyToMessageBuilder.new(
+      message: self,
+      in_reply_to: in_reply_to,
+      in_reply_to_external_id: in_reply_to_external_id
+    ).perform
   end
 
   def ensure_content_type
diff --git a/app/services/messages/in_reply_to_message_builder.rb b/app/services/messages/in_reply_to_message_builder.rb
new file mode 100644
index 000000000..be4724694
--- /dev/null
+++ b/app/services/messages/in_reply_to_message_builder.rb
@@ -0,0 +1,24 @@
+class Messages::InReplyToMessageBuilder
+  pattr_initialize [:message!, :in_reply_to!, :in_reply_to_external_id!]
+
+  delegate :conversation, to: :message
+
+  def perform
+    set_in_reply_to_attribute if @in_reply_to.present? || @in_reply_to_external_id.present?
+  end
+
+  private
+
+  def set_in_reply_to_attribute
+    @message.content_attributes[:in_reply_to_external_id] = in_reply_to_message.try(:source_id)
+    @message.content_attributes[:in_reply_to] = in_reply_to_message.try(:id)
+  end
+
+  def in_reply_to_message
+    return conversation.messages.find_by(id: @in_reply_to) if @in_reply_to.present?
+
+    return conversation.messages.find_by(source_id: @in_reply_to_external_id) if @in_reply_to_external_id
+
+    nil
+  end
+end
diff --git a/app/services/whatsapp/incoming_message_base_service.rb b/app/services/whatsapp/incoming_message_base_service.rb
index 0fd758979..2d3b4efd3 100644
--- a/app/services/whatsapp/incoming_message_base_service.rb
+++ b/app/services/whatsapp/incoming_message_base_service.rb
@@ -144,8 +144,7 @@ class Whatsapp::IncomingMessageBaseService
       message_type: :incoming,
       sender: @contact,
       source_id: message[:id].to_s,
-      in_reply_to_external_id: @in_reply_to_external_id,
-      in_reply_to: @in_reply_to
+      in_reply_to_external_id: @in_reply_to_external_id
     )
   end
 
diff --git a/app/services/whatsapp/incoming_message_service_helpers.rb b/app/services/whatsapp/incoming_message_service_helpers.rb
index ad2fccd03..76a31576e 100644
--- a/app/services/whatsapp/incoming_message_service_helpers.rb
+++ b/app/services/whatsapp/incoming_message_service_helpers.rb
@@ -88,15 +88,7 @@ module Whatsapp::IncomingMessageServiceHelpers
   end
 
   def process_in_reply_to(message)
-    return if message['context'].blank?
-
-    @in_reply_to_external_id = message['context']['id']
-
-    return if @in_reply_to_external_id.blank?
-
-    in_reply_to_message = Message.find_by(source_id: @in_reply_to_external_id)
-
-    @in_reply_to = in_reply_to_message.id if in_reply_to_message.present?
+    @in_reply_to_external_id = message['context']&.[]('id')
   end
 
   def find_message_by_source_id(source_id)
diff --git a/app/services/whatsapp/providers/whatsapp_cloud_service.rb b/app/services/whatsapp/providers/whatsapp_cloud_service.rb
index d1092e2ff..f1af38e36 100644
--- a/app/services/whatsapp/providers/whatsapp_cloud_service.rb
+++ b/app/services/whatsapp/providers/whatsapp_cloud_service.rb
@@ -78,6 +78,7 @@ class Whatsapp::Providers::WhatsappCloudService < Whatsapp::Providers::BaseServi
       headers: api_headers,
       body: {
         messaging_product: 'whatsapp',
+        context: whatsapp_reply_context(message),
         to: phone_number,
         text: { body: message.content },
         type: 'text'
@@ -100,6 +101,7 @@ class Whatsapp::Providers::WhatsappCloudService < Whatsapp::Providers::BaseServi
       headers: api_headers,
       body: {
         :messaging_product => 'whatsapp',
+        :context => whatsapp_reply_context(message),
         'to' => phone_number,
         'type' => type,
         type.to_s => type_content
@@ -132,6 +134,15 @@ class Whatsapp::Providers::WhatsappCloudService < Whatsapp::Providers::BaseServi
     }
   end
 
+  def whatsapp_reply_context(message)
+    reply_to = message.content_attributes[:in_reply_to_external_id]
+    return nil if reply_to.blank?
+
+    {
+      message_id: reply_to
+    }
+  end
+
   def send_interactive_text_message(phone_number, message)
     payload = create_payload_based_on_items(message)
 
diff --git a/spec/services/whatsapp/providers/whatsapp_cloud_service_spec.rb b/spec/services/whatsapp/providers/whatsapp_cloud_service_spec.rb
index 1bf115476..7c2b79b8d 100644
--- a/spec/services/whatsapp/providers/whatsapp_cloud_service_spec.rb
+++ b/spec/services/whatsapp/providers/whatsapp_cloud_service_spec.rb
@@ -3,8 +3,18 @@ require 'rails_helper'
 describe Whatsapp::Providers::WhatsappCloudService do
   subject(:service) { described_class.new(whatsapp_channel: whatsapp_channel) }
 
+  let(:conversation) { create(:conversation, inbox: whatsapp_channel.inbox) }
   let(:whatsapp_channel) { create(:channel_whatsapp, provider: 'whatsapp_cloud', validate_provider_config: false, sync_templates: false) }
-  let(:message) { create(:message, message_type: :outgoing, content: 'test', inbox: whatsapp_channel.inbox) }
+
+  let(:message) do
+    create(:message, conversation: conversation, message_type: :outgoing, content: 'test', inbox: whatsapp_channel.inbox, source_id: 'external_id')
+  end
+
+  let(:message_with_reply) do
+    create(:message, conversation: conversation, message_type: :outgoing, content: 'reply', inbox: whatsapp_channel.inbox,
+                     content_attributes: { in_reply_to: message.id })
+  end
+
   let(:response_headers) { { 'Content-Type' => 'application/json' } }
   let(:whatsapp_response) { { messages: [{ id: 'message_id' }] } }
 
@@ -19,6 +29,7 @@ describe Whatsapp::Providers::WhatsappCloudService do
           .with(
             body: {
               messaging_product: 'whatsapp',
+              context: nil,
               to: '+123456789',
               text: { body: message.content },
               type: 'text'
@@ -28,6 +39,23 @@ describe Whatsapp::Providers::WhatsappCloudService do
         expect(service.send_message('+123456789', message)).to eq 'message_id'
       end
 
+      it 'calls message endpoints for a reply to messages' do
+        stub_request(:post, 'https://graph.facebook.com/v13.0/123456789/messages')
+          .with(
+            body: {
+              messaging_product: 'whatsapp',
+              context: {
+                message_id: message.source_id
+              },
+              to: '+123456789',
+              text: { body: message_with_reply.content },
+              type: 'text'
+            }.to_json
+          )
+          .to_return(status: 200, body: whatsapp_response.to_json, headers: response_headers)
+        expect(service.send_message('+123456789', message_with_reply)).to eq 'message_id'
+      end
+
       it 'calls message endpoints for image attachment message messages' do
         attachment = message.attachments.new(account_id: message.account_id, file_type: :image)
         attachment.file.attach(io: Rails.root.join('spec/assets/avatar.png').open, filename: 'avatar.png', content_type: 'image/png')