diff --git a/app/javascript/dashboard/components-next/message/Message.vue b/app/javascript/dashboard/components-next/message/Message.vue
index 1993df60e..528d78030 100644
--- a/app/javascript/dashboard/components-next/message/Message.vue
+++ b/app/javascript/dashboard/components-next/message/Message.vue
@@ -30,6 +30,11 @@ import MessageStatus from './MessageStatus.vue';
  * @property {string} type - Type of sender
  */
 
+/**
+ * @typedef {Object} ContentAttributes
+ * @property {string} externalError - an error message to be shown if the message failed to send
+ */
+
 /**
  * @typedef {Object} Props
  * @property {number} id - The unique identifier for the message
@@ -38,6 +43,7 @@ import MessageStatus from './MessageStatus.vue';
  * @property {boolean} [private=false] - Whether the message is private
  * @property {number} createdAt - Timestamp when the message was created
  * @property {Sender|null} [sender=null] - The sender information
+ * @property {ContentAttributes} [contentAttributes={}] - Additional attributes of the message content
  * @property {number|null} [senderId=null] - The ID of the sender
  * @property {string|null} [senderType=null] - The type of the sender
  * @property {string|null} [error=null] - Error message if the message failed to send
@@ -81,9 +87,9 @@ const props = defineProps({
     type: String,
     required: true,
   },
-  error: {
-    type: String,
-    default: '',
+  contentAttributes: {
+    type: Object,
+    default: () => {},
   },
   currentUserId: {
     type: Number,
@@ -101,7 +107,7 @@ const props = defineProps({
  */
 const variant = computed(() => {
   if (props.private) return MESSAGE_VARIANTS.PRIVATE;
-  if (props.error) return MESSAGE_VARIANTS.ERROR;
+  if (props.status === MESSAGE_STATUS.FAILED) return MESSAGE_VARIANTS.ERROR;
 
   const variants = {
     [MESSAGE_TYPES.INCOMING]: MESSAGE_VARIANTS.USER,
@@ -207,10 +213,10 @@ const shouldShowAvatar = computed(() => {
         class="[grid-area:bubble]"
       />
       <MessageError
-        v-if="error"
+        v-if="contentAttributes.externalError"
         class="[grid-area:meta]"
         :class="flexOrientationClass"
-        :error="error"
+        :error="contentAttributes.externalError"
       />
       <div
         v-else-if="!shouldGroupWithNext"
diff --git a/app/javascript/dashboard/components-next/message/Messages.story.vue b/app/javascript/dashboard/components-next/message/Messages.story.vue
index 9d05534a2..84cad389f 100644
--- a/app/javascript/dashboard/components-next/message/Messages.story.vue
+++ b/app/javascript/dashboard/components-next/message/Messages.story.vue
@@ -2,715 +2,719 @@
 import Message from './Message.vue';
 import camelcaseKeys from 'camelcase-keys';
 
-const messages = [
-  {
-    id: 5272,
-    content: 'Hey, how are ya, I had a few questions about Chatwoot?',
-    inbox_id: 475,
-    conversation_id: 43,
-    message_type: 0,
-    content_type: 'text',
-    status: 'sent',
-    content_attributes: {
-      in_reply_to: null,
+const messages = camelcaseKeys(
+  [
+    {
+      id: 5272,
+      content: 'Hey, how are ya, I had a few questions about Chatwoot?',
+      inbox_id: 475,
+      conversation_id: 43,
+      message_type: 0,
+      content_type: 'text',
+      status: 'sent',
+      content_attributes: {
+        in_reply_to: null,
+      },
+      created_at: 1732195656,
+      private: false,
+      source_id: null,
+      sender: {
+        additional_attributes: {},
+        custom_attributes: {},
+        email: 'hey@example.com',
+        id: 597,
+        identifier: null,
+        name: 'hey',
+        phone_number: null,
+        thumbnail: '',
+        type: 'contact',
+      },
     },
-    created_at: 1732195656,
-    private: false,
-    source_id: null,
-    sender: {
+    {
+      id: 5273,
+      content: 'Give the team a way to reach you.',
+      inbox_id: 475,
+      conversation_id: 43,
+      message_type: 3,
+      content_type: 'text',
+      status: 'read',
+      content_attributes: {},
+      created_at: 1732195656,
+      private: false,
+      source_id: null,
+    },
+    {
+      id: 5274,
+      content: 'Get notified by email',
+      account_id: 1,
+      inbox_id: 475,
+      conversation_id: 43,
+      message_type: 3,
+      created_at: 1732195656,
+      updated_at: '2024-11-21T13:27:53.612Z',
+      private: false,
+      status: 'read',
+      source_id: null,
+      content_type: 'input_email',
+      content_attributes: {
+        submitted_email: 'hey@example.com',
+      },
+      sender_type: null,
+      sender_id: null,
+      external_source_ids: {},
       additional_attributes: {},
-      custom_attributes: {},
-      email: 'hey@example.com',
-      id: 597,
-      identifier: null,
-      name: 'hey',
-      phone_number: null,
-      thumbnail: '',
-      type: 'contact',
-    },
-  },
-  {
-    id: 5273,
-    content: 'Give the team a way to reach you.',
-    inbox_id: 475,
-    conversation_id: 43,
-    message_type: 3,
-    content_type: 'text',
-    status: 'read',
-    content_attributes: {},
-    created_at: 1732195656,
-    private: false,
-    source_id: null,
-  },
-  {
-    id: 5274,
-    content: 'Get notified by email',
-    account_id: 1,
-    inbox_id: 475,
-    conversation_id: 43,
-    message_type: 3,
-    created_at: 1732195656,
-    updated_at: '2024-11-21T13:27:53.612Z',
-    private: false,
-    status: 'read',
-    source_id: null,
-    content_type: 'input_email',
-    content_attributes: {
-      submitted_email: 'hey@example.com',
-    },
-    sender_type: null,
-    sender_id: null,
-    external_source_ids: {},
-    additional_attributes: {},
-    processed_message_content: 'Get notified by email',
-    sentiment: {},
-    conversation: {
-      assignee_id: null,
-      unread_count: 1,
-      last_activity_at: 1732195656,
-      contact_inbox: {
-        source_id: 'b018c554-8e17-4102-8a0b-f6d20d021017',
+      processed_message_content: 'Get notified by email',
+      sentiment: {},
+      conversation: {
+        assignee_id: null,
+        unread_count: 1,
+        last_activity_at: 1732195656,
+        contact_inbox: {
+          source_id: 'b018c554-8e17-4102-8a0b-f6d20d021017',
+        },
       },
     },
-  },
-  {
-    id: 5275,
-    content:
-      'Does the Startup plan include the two users from the Free plan, or do I have to buy those separately?',
-    account_id: 1,
-    inbox_id: 475,
-    conversation_id: 43,
-    message_type: 0,
-    created_at: 1732195735,
-    updated_at: '2024-11-21T13:28:55.508Z',
-    private: false,
-    status: 'sent',
-    source_id: null,
-    content_type: 'text',
-    content_attributes: {
-      in_reply_to: null,
-    },
-    sender_type: 'Contact',
-    sender_id: 597,
-    external_source_ids: {},
-    additional_attributes: {},
-    processed_message_content:
-      'Does the Startup plan include the two users from the Free plan, or do I have to buy those separately?',
-    sentiment: {},
-    conversation: {
-      assignee_id: null,
-      unread_count: 1,
-      last_activity_at: 1732195735,
-      contact_inbox: {
-        source_id: 'b018c554-8e17-4102-8a0b-f6d20d021017',
+    {
+      id: 5275,
+      content:
+        'Does the Startup plan include the two users from the Free plan, or do I have to buy those separately?',
+      account_id: 1,
+      inbox_id: 475,
+      conversation_id: 43,
+      message_type: 0,
+      created_at: 1732195735,
+      updated_at: '2024-11-21T13:28:55.508Z',
+      private: false,
+      status: 'sent',
+      source_id: null,
+      content_type: 'text',
+      content_attributes: {
+        in_reply_to: null,
       },
-    },
-    sender: {
+      sender_type: 'Contact',
+      sender_id: 597,
+      external_source_ids: {},
       additional_attributes: {},
-      custom_attributes: {},
-      email: 'hey@example.com',
-      id: 597,
-      identifier: null,
-      name: 'hey',
-      phone_number: null,
-      thumbnail: '',
-      type: 'contact',
-    },
-  },
-  {
-    conversation_id: 43,
-    status: 'read',
-    content_type: 'text',
-    processed_message_content: 'John self-assigned this conversation',
-    id: 5276,
-    content: 'John self-assigned this conversation',
-    account_id: 1,
-    inbox_id: 475,
-    message_type: 2,
-    created_at: 1732195741,
-    updated_at: '2024-11-21T13:30:26.788Z',
-    private: false,
-    source_id: null,
-    content_attributes: {},
-    sender_type: null,
-    sender_id: null,
-    external_source_ids: {},
-    additional_attributes: {},
-    sentiment: {},
-    conversation: {
-      assignee_id: 1,
-      unread_count: 0,
-      last_activity_at: 1732195826,
-      contact_inbox: {
-        source_id: 'b018c554-8e17-4102-8a0b-f6d20d021017',
+      processed_message_content:
+        'Does the Startup plan include the two users from the Free plan, or do I have to buy those separately?',
+      sentiment: {},
+      conversation: {
+        assignee_id: null,
+        unread_count: 1,
+        last_activity_at: 1732195735,
+        contact_inbox: {
+          source_id: 'b018c554-8e17-4102-8a0b-f6d20d021017',
+        },
+      },
+      sender: {
+        additional_attributes: {},
+        custom_attributes: {},
+        email: 'hey@example.com',
+        id: 597,
+        identifier: null,
+        name: 'hey',
+        phone_number: null,
+        thumbnail: '',
+        type: 'contact',
       },
     },
-    previous_changes: {
-      updated_at: ['2024-11-21T13:29:01.570Z', '2024-11-21T13:30:26.788Z'],
-      status: ['sent', 'read'],
-    },
-  },
-  {
-    conversation_id: 43,
-    status: 'read',
-    content_type: 'text',
-    processed_message_content:
-      'Hey thanks for your interest in upgrading, no, the seats are not included, you will have to purchase them alongside the rest. How many seats are you planning to upgrade to?',
-    id: 5277,
-    content:
-      'Hey thanks for your interest in upgrading, no, the seats are not included, you will have to purchase them alongside the rest. How many seats are you planning to upgrade to?',
-    account_id: 1,
-    inbox_id: 475,
-    message_type: 1,
-    created_at: 1732195826,
-    updated_at: '2024-11-21T13:30:26.837Z',
-    private: false,
-    source_id: null,
-    content_attributes: {},
-    sender_type: 'User',
-    sender_id: 1,
-    external_source_ids: {},
-    additional_attributes: {},
-    sentiment: {},
-    conversation: {
-      assignee_id: 1,
-      unread_count: 0,
-      last_activity_at: 1732195826,
-      contact_inbox: {
-        source_id: 'b018c554-8e17-4102-8a0b-f6d20d021017',
-      },
-    },
-    sender: {
-      id: 1,
-      name: 'John',
-      available_name: 'John',
-      avatar_url:
-        'http://localhost:3000/rails/active_storage/representations/redirect/eyJfcmFpbHMiOnsibWVzc2FnZSI6IkJBaHBBaDBLIiwiZXhwIjpudWxsLCJwdXIiOiJibG9iX2lkIn19--4e625d80e7ef2dc41354392bc214832fbe640840/eyJfcmFpbHMiOnsibWVzc2FnZSI6IkJBaDdCem9MWm05eWJXRjBTU0lJY0c1bkJqb0dSVlE2RTNKbGMybDZaVjkwYjE5bWFXeHNXd2RwQWZvdyIsImV4cCI6bnVsbCwicHVyIjoidmFyaWF0aW9uIn19--ebe60765d222d11ade39165eae49cc4b2de18d89/picologo.png',
-      type: 'user',
-      availability_status: null,
-      thumbnail:
-        'http://localhost:3000/rails/active_storage/representations/redirect/eyJfcmFpbHMiOnsibWVzc2FnZSI6IkJBaHBBaDBLIiwiZXhwIjpudWxsLCJwdXIiOiJibG9iX2lkIn19--4e625d80e7ef2dc41354392bc214832fbe640840/eyJfcmFpbHMiOnsibWVzc2FnZSI6IkJBaDdCem9MWm05eWJXRjBTU0lJY0c1bkJqb0dSVlE2RTNKbGMybDZaVjkwYjE5bWFXeHNXd2RwQWZvdyIsImV4cCI6bnVsbCwicHVyIjoidmFyaWF0aW9uIn19--ebe60765d222d11ade39165eae49cc4b2de18d89/picologo.png',
-    },
-    previous_changes: {
-      updated_at: ['2024-11-21T13:30:26.149Z', '2024-11-21T13:30:26.837Z'],
-      status: ['sent', 'read'],
-    },
-  },
-  {
-    id: 5278,
-    content: "Oh, that's unfortunate",
-    account_id: 1,
-    inbox_id: 475,
-    conversation_id: 43,
-    message_type: 0,
-    created_at: 1732195820,
-    updated_at: '2024-11-21T13:30:38.070Z',
-    private: false,
-    status: 'sent',
-    source_id: null,
-    content_type: 'text',
-    content_attributes: {
-      in_reply_to: null,
-    },
-    sender_type: 'Contact',
-    sender_id: 597,
-    external_source_ids: {},
-    additional_attributes: {},
-    processed_message_content: "Oh, that's unfortunate",
-    sentiment: {},
-    conversation: {
-      assignee_id: 1,
-      unread_count: 1,
-      last_activity_at: 1732195820,
-      contact_inbox: {
-        source_id: 'b018c554-8e17-4102-8a0b-f6d20d021017',
-      },
-    },
-    sender: {
+    {
+      conversation_id: 43,
+      status: 'read',
+      content_type: 'text',
+      processed_message_content: 'John self-assigned this conversation',
+      id: 5276,
+      content: 'John self-assigned this conversation',
+      account_id: 1,
+      inbox_id: 475,
+      message_type: 2,
+      created_at: 1732195741,
+      updated_at: '2024-11-21T13:30:26.788Z',
+      private: false,
+      source_id: null,
+      content_attributes: {},
+      sender_type: null,
+      sender_id: null,
+      external_source_ids: {},
       additional_attributes: {},
-      custom_attributes: {},
-      email: 'hey@example.com',
-      id: 597,
-      identifier: null,
-      name: 'hey',
-      phone_number: null,
-      thumbnail: '',
-      type: 'contact',
-    },
-  },
-  {
-    id: 5279,
-    content:
-      'I plan to upgrade to 4 agents for now, but will grow to 6 in the next three months. ',
-    account_id: 1,
-    inbox_id: 475,
-    conversation_id: 43,
-    message_type: 0,
-    created_at: 1732195820,
-    updated_at: '2024-11-21T13:31:05.284Z',
-    private: false,
-    status: 'sent',
-    source_id: null,
-    content_type: 'text',
-    content_attributes: {
-      in_reply_to: null,
-    },
-    sender_type: 'Contact',
-    sender_id: 597,
-    external_source_ids: {},
-    additional_attributes: {},
-    processed_message_content:
-      'I plan to upgrade to 4 agents for now, but will grow to 6 in the next three months. ',
-    sentiment: {},
-    conversation: {
-      assignee_id: 1,
-      unread_count: 1,
-      last_activity_at: 1732195885,
-      contact_inbox: {
-        source_id: 'b018c554-8e17-4102-8a0b-f6d20d021017',
+      sentiment: {},
+      conversation: {
+        assignee_id: 1,
+        unread_count: 0,
+        last_activity_at: 1732195826,
+        contact_inbox: {
+          source_id: 'b018c554-8e17-4102-8a0b-f6d20d021017',
+        },
+      },
+      previous_changes: {
+        updated_at: ['2024-11-21T13:29:01.570Z', '2024-11-21T13:30:26.788Z'],
+        status: ['sent', 'read'],
       },
     },
-    sender: {
+    {
+      conversation_id: 43,
+      status: 'read',
+      content_type: 'text',
+      processed_message_content:
+        'Hey thanks for your interest in upgrading, no, the seats are not included, you will have to purchase them alongside the rest. How many seats are you planning to upgrade to?',
+      id: 5277,
+      content:
+        'Hey thanks for your interest in upgrading, no, the seats are not included, you will have to purchase them alongside the rest. How many seats are you planning to upgrade to?',
+      account_id: 1,
+      inbox_id: 475,
+      message_type: 1,
+      created_at: 1732195826,
+      updated_at: '2024-11-21T13:30:26.837Z',
+      private: false,
+      source_id: null,
+      content_attributes: {},
+      sender_type: 'User',
+      sender_id: 1,
+      external_source_ids: {},
       additional_attributes: {},
-      custom_attributes: {},
-      email: 'hey@example.com',
-      id: 597,
-      identifier: null,
-      name: 'hey',
-      phone_number: null,
-      thumbnail: '',
-      type: 'contact',
+      sentiment: {},
+      conversation: {
+        assignee_id: 1,
+        unread_count: 0,
+        last_activity_at: 1732195826,
+        contact_inbox: {
+          source_id: 'b018c554-8e17-4102-8a0b-f6d20d021017',
+        },
+      },
+      sender: {
+        id: 1,
+        name: 'John',
+        available_name: 'John',
+        avatar_url:
+          'http://localhost:3000/rails/active_storage/representations/redirect/eyJfcmFpbHMiOnsibWVzc2FnZSI6IkJBaHBBaDBLIiwiZXhwIjpudWxsLCJwdXIiOiJibG9iX2lkIn19--4e625d80e7ef2dc41354392bc214832fbe640840/eyJfcmFpbHMiOnsibWVzc2FnZSI6IkJBaDdCem9MWm05eWJXRjBTU0lJY0c1bkJqb0dSVlE2RTNKbGMybDZaVjkwYjE5bWFXeHNXd2RwQWZvdyIsImV4cCI6bnVsbCwicHVyIjoidmFyaWF0aW9uIn19--ebe60765d222d11ade39165eae49cc4b2de18d89/picologo.png',
+        type: 'user',
+        availability_status: null,
+        thumbnail:
+          'http://localhost:3000/rails/active_storage/representations/redirect/eyJfcmFpbHMiOnsibWVzc2FnZSI6IkJBaHBBaDBLIiwiZXhwIjpudWxsLCJwdXIiOiJibG9iX2lkIn19--4e625d80e7ef2dc41354392bc214832fbe640840/eyJfcmFpbHMiOnsibWVzc2FnZSI6IkJBaDdCem9MWm05eWJXRjBTU0lJY0c1bkJqb0dSVlE2RTNKbGMybDZaVjkwYjE5bWFXeHNXd2RwQWZvdyIsImV4cCI6bnVsbCwicHVyIjoidmFyaWF0aW9uIn19--ebe60765d222d11ade39165eae49cc4b2de18d89/picologo.png',
+      },
+      previous_changes: {
+        updated_at: ['2024-11-21T13:30:26.149Z', '2024-11-21T13:30:26.837Z'],
+        status: ['sent', 'read'],
+      },
+    },
+    {
+      id: 5278,
+      content: "Oh, that's unfortunate",
+      account_id: 1,
+      inbox_id: 475,
+      conversation_id: 43,
+      message_type: 0,
+      created_at: 1732195820,
+      updated_at: '2024-11-21T13:30:38.070Z',
+      private: false,
+      status: 'sent',
+      source_id: null,
+      content_type: 'text',
+      content_attributes: {
+        in_reply_to: null,
+      },
+      sender_type: 'Contact',
+      sender_id: 597,
+      external_source_ids: {},
+      additional_attributes: {},
+      processed_message_content: "Oh, that's unfortunate",
+      sentiment: {},
+      conversation: {
+        assignee_id: 1,
+        unread_count: 1,
+        last_activity_at: 1732195820,
+        contact_inbox: {
+          source_id: 'b018c554-8e17-4102-8a0b-f6d20d021017',
+        },
+      },
+      sender: {
+        additional_attributes: {},
+        custom_attributes: {},
+        email: 'hey@example.com',
+        id: 597,
+        identifier: null,
+        name: 'hey',
+        phone_number: null,
+        thumbnail: '',
+        type: 'contact',
+      },
+    },
+    {
+      id: 5279,
+      content:
+        'I plan to upgrade to 4 agents for now, but will grow to 6 in the next three months. ',
+      account_id: 1,
+      inbox_id: 475,
+      conversation_id: 43,
+      message_type: 0,
+      created_at: 1732195820,
+      updated_at: '2024-11-21T13:31:05.284Z',
+      private: false,
+      status: 'sent',
+      source_id: null,
+      content_type: 'text',
+      content_attributes: {
+        in_reply_to: null,
+      },
+      sender_type: 'Contact',
+      sender_id: 597,
+      external_source_ids: {},
+      additional_attributes: {},
+      processed_message_content:
+        'I plan to upgrade to 4 agents for now, but will grow to 6 in the next three months. ',
+      sentiment: {},
+      conversation: {
+        assignee_id: 1,
+        unread_count: 1,
+        last_activity_at: 1732195885,
+        contact_inbox: {
+          source_id: 'b018c554-8e17-4102-8a0b-f6d20d021017',
+        },
+      },
+      sender: {
+        additional_attributes: {},
+        custom_attributes: {},
+        email: 'hey@example.com',
+        id: 597,
+        identifier: null,
+        name: 'hey',
+        phone_number: null,
+        thumbnail: '',
+        type: 'contact',
+      },
     },
-  },
 
-  {
-    id: 5280,
-    content: 'Is it possible to get a discount?',
-    account_id: 1,
-    inbox_id: 475,
-    conversation_id: 43,
-    message_type: 0,
-    created_at: 1732195886,
-    updated_at: '2024-11-21T13:31:12.545Z',
-    private: false,
-    status: 'sent',
-    source_id: null,
-    content_type: 'text',
-    content_attributes: {
-      in_reply_to: null,
-    },
-    sender_type: 'Contact',
-    sender_id: 597,
-    external_source_ids: {},
-    additional_attributes: {},
-    processed_message_content: 'Is it possible to get a discount?',
-    sentiment: {},
-    conversation: {
-      assignee_id: 1,
-      unread_count: 1,
-      last_activity_at: 1732195872,
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+        available_name: 'John',
+        avatar_url:
+          'http://localhost:3000/rails/active_storage/representations/redirect/eyJfcmFpbHMiOnsibWVzc2FnZSI6IkJBaHBBaDBLIiwiZXhwIjpudWxsLCJwdXIiOiJibG9iX2lkIn19--4e625d80e7ef2dc41354392bc214832fbe640840/eyJfcmFpbHMiOnsibWVzc2FnZSI6IkJBaDdCem9MWm05eWJXRjBTU0lJY0c1bkJqb0dSVlE2RTNKbGMybDZaVjkwYjE5bWFXeHNXd2RwQWZvdyIsImV4cCI6bnVsbCwicHVyIjoidmFyaWF0aW9uIn19--ebe60765d222d11ade39165eae49cc4b2de18d89/picologo.png',
+        type: 'user',
+        availability_status: null,
+        thumbnail:
+          'http://localhost:3000/rails/active_storage/representations/redirect/eyJfcmFpbHMiOnsibWVzc2FnZSI6IkJBaHBBaDBLIiwiZXhwIjpudWxsLCJwdXIiOiJibG9iX2lkIn19--4e625d80e7ef2dc41354392bc214832fbe640840/eyJfcmFpbHMiOnsibWVzc2FnZSI6IkJBaDdCem9MWm05eWJXRjBTU0lJY0c1bkJqb0dSVlE2RTNKbGMybDZaVjkwYjE5bWFXeHNXd2RwQWZvdyIsImV4cCI6bnVsbCwicHVyIjoidmFyaWF0aW9uIn19--ebe60765d222d11ade39165eae49cc4b2de18d89/picologo.png',
+      },
+      previous_changes: {
+        updated_at: ['2024-11-21T13:33:11.667Z', '2024-11-21T13:33:12.229Z'],
+        status: ['sent', 'read'],
       },
     },
-    sender: {
-      id: 1,
-      name: 'John',
-      available_name: 'John',
-      avatar_url:
-        'http://localhost:3000/rails/active_storage/representations/redirect/eyJfcmFpbHMiOnsibWVzc2FnZSI6IkJBaHBBaDBLIiwiZXhwIjpudWxsLCJwdXIiOiJibG9iX2lkIn19--4e625d80e7ef2dc41354392bc214832fbe640840/eyJfcmFpbHMiOnsibWVzc2FnZSI6IkJBaDdCem9MWm05eWJXRjBTU0lJY0c1bkJqb0dSVlE2RTNKbGMybDZaVjkwYjE5bWFXeHNXd2RwQWZvdyIsImV4cCI6bnVsbCwicHVyIjoidmFyaWF0aW9uIn19--ebe60765d222d11ade39165eae49cc4b2de18d89/picologo.png',
-      type: 'user',
-      availability_status: null,
-      thumbnail:
-        'http://localhost:3000/rails/active_storage/representations/redirect/eyJfcmFpbHMiOnsibWVzc2FnZSI6IkJBaHBBaDBLIiwiZXhwIjpudWxsLCJwdXIiOiJibG9iX2lkIn19--4e625d80e7ef2dc41354392bc214832fbe640840/eyJfcmFpbHMiOnsibWVzc2FnZSI6IkJBaDdCem9MWm05eWJXRjBTU0lJY0c1bkJqb0dSVlE2RTNKbGMybDZaVjkwYjE5bWFXeHNXd2RwQWZvdyIsImV4cCI6bnVsbCwicHVyIjoidmFyaWF0aW9uIn19--ebe60765d222d11ade39165eae49cc4b2de18d89/picologo.png',
-    },
-    previous_changes: {
-      updated_at: ['2024-11-21T13:33:33.511Z', '2024-11-21T13:33:33.879Z'],
-      status: ['sent', 'read'],
-    },
-  },
-  {
-    id: 5287,
-    content: 'John set the priority to urgent',
-    account_id: 1,
-    inbox_id: 475,
-    conversation_id: 43,
-    message_type: 2,
-    created_at: 1732196017,
-    updated_at: '2024-11-21T13:33:37.569Z',
-    private: false,
-    status: 'sent',
-    source_id: null,
-    content_type: 'text',
-    content_attributes: {},
-    sender_type: null,
-    sender_id: null,
-    external_source_ids: {},
-    additional_attributes: {},
-    processed_message_content: 'John set the priority to urgent',
-    sentiment: {},
-    conversation: {
-      assignee_id: 1,
-      unread_count: 0,
-      last_activity_at: 1732196017,
-      contact_inbox: {
-        source_id: 'b018c554-8e17-4102-8a0b-f6d20d021017',
+    {
+      conversation_id: 43,
+      status: 'failed',
+      content_type: 'text',
+      processed_message_content:
+        "Let us know if you have any questions, I'll close this conversation for now",
+      id: 5286,
+      content:
+        "Let us know if you have any questions, I'll close this conversation for now",
+      account_id: 1,
+      inbox_id: 475,
+      message_type: 1,
+      created_at: 1732196013,
+      updated_at: '2024-11-21T13:33:33.879Z',
+      private: false,
+      source_id: null,
+      content_attributes: {
+        external_error:
+          'Business account is restricted from messaging users in this country.',
+      },
+      sender_type: 'User',
+      sender_id: 1,
+      external_source_ids: {},
+      additional_attributes: {},
+      sentiment: {},
+      conversation: {
+        assignee_id: 1,
+        unread_count: 0,
+        last_activity_at: 1732196013,
+        contact_inbox: {
+          source_id: 'b018c554-8e17-4102-8a0b-f6d20d021017',
+        },
+      },
+      sender: {
+        id: 1,
+        name: 'John',
+        available_name: 'John',
+        avatar_url:
+          'http://localhost:3000/rails/active_storage/representations/redirect/eyJfcmFpbHMiOnsibWVzc2FnZSI6IkJBaHBBaDBLIiwiZXhwIjpudWxsLCJwdXIiOiJibG9iX2lkIn19--4e625d80e7ef2dc41354392bc214832fbe640840/eyJfcmFpbHMiOnsibWVzc2FnZSI6IkJBaDdCem9MWm05eWJXRjBTU0lJY0c1bkJqb0dSVlE2RTNKbGMybDZaVjkwYjE5bWFXeHNXd2RwQWZvdyIsImV4cCI6bnVsbCwicHVyIjoidmFyaWF0aW9uIn19--ebe60765d222d11ade39165eae49cc4b2de18d89/picologo.png',
+        type: 'user',
+        availability_status: null,
+        thumbnail:
+          'http://localhost:3000/rails/active_storage/representations/redirect/eyJfcmFpbHMiOnsibWVzc2FnZSI6IkJBaHBBaDBLIiwiZXhwIjpudWxsLCJwdXIiOiJibG9iX2lkIn19--4e625d80e7ef2dc41354392bc214832fbe640840/eyJfcmFpbHMiOnsibWVzc2FnZSI6IkJBaDdCem9MWm05eWJXRjBTU0lJY0c1bkJqb0dSVlE2RTNKbGMybDZaVjkwYjE5bWFXeHNXd2RwQWZvdyIsImV4cCI6bnVsbCwicHVyIjoidmFyaWF0aW9uIn19--ebe60765d222d11ade39165eae49cc4b2de18d89/picologo.png',
+      },
+      previous_changes: {
+        updated_at: ['2024-11-21T13:33:33.511Z', '2024-11-21T13:33:33.879Z'],
+        status: ['sent', 'read'],
       },
     },
-  },
-  {
-    id: 5288,
-    content: 'John added billing',
-    account_id: 1,
-    inbox_id: 475,
-    conversation_id: 43,
-    message_type: 2,
-    created_at: 1732196020,
-    updated_at: '2024-11-21T13:33:40.207Z',
-    private: false,
-    status: 'sent',
-    source_id: null,
-    content_type: 'text',
-    content_attributes: {},
-    sender_type: null,
-    sender_id: null,
-    external_source_ids: {},
-    additional_attributes: {},
-    processed_message_content: 'John added billing',
-    sentiment: {},
-    conversation: {
-      assignee_id: 1,
-      unread_count: 0,
-      last_activity_at: 1732196020,
-      contact_inbox: {
-        source_id: 'b018c554-8e17-4102-8a0b-f6d20d021017',
+    {
+      id: 5287,
+      content: 'John set the priority to urgent',
+      account_id: 1,
+      inbox_id: 475,
+      conversation_id: 43,
+      message_type: 2,
+      created_at: 1732196017,
+      updated_at: '2024-11-21T13:33:37.569Z',
+      private: false,
+      status: 'sent',
+      source_id: null,
+      content_type: 'text',
+      content_attributes: {},
+      sender_type: null,
+      sender_id: null,
+      external_source_ids: {},
+      additional_attributes: {},
+      processed_message_content: 'John set the priority to urgent',
+      sentiment: {},
+      conversation: {
+        assignee_id: 1,
+        unread_count: 0,
+        last_activity_at: 1732196017,
+        contact_inbox: {
+          source_id: 'b018c554-8e17-4102-8a0b-f6d20d021017',
+        },
       },
     },
-  },
-  {
-    id: 5289,
-    content: 'John added delivery',
-    account_id: 1,
-    inbox_id: 475,
-    conversation_id: 43,
-    message_type: 2,
-    created_at: 1732196020,
-    updated_at: '2024-11-21T13:33:40.822Z',
-    private: false,
-    status: 'sent',
-    source_id: null,
-    content_type: 'text',
-    content_attributes: {},
-    sender_type: null,
-    sender_id: null,
-    external_source_ids: {},
-    additional_attributes: {},
-    processed_message_content: 'John added delivery',
-    sentiment: {},
-    conversation: {
-      assignee_id: 1,
-      unread_count: 0,
-      last_activity_at: 1732196020,
-      contact_inbox: {
-        source_id: 'b018c554-8e17-4102-8a0b-f6d20d021017',
+    {
+      id: 5288,
+      content: 'John added billing',
+      account_id: 1,
+      inbox_id: 475,
+      conversation_id: 43,
+      message_type: 2,
+      created_at: 1732196020,
+      updated_at: '2024-11-21T13:33:40.207Z',
+      private: false,
+      status: 'sent',
+      source_id: null,
+      content_type: 'text',
+      content_attributes: {},
+      sender_type: null,
+      sender_id: null,
+      external_source_ids: {},
+      additional_attributes: {},
+      processed_message_content: 'John added billing',
+      sentiment: {},
+      conversation: {
+        assignee_id: 1,
+        unread_count: 0,
+        last_activity_at: 1732196020,
+        contact_inbox: {
+          source_id: 'b018c554-8e17-4102-8a0b-f6d20d021017',
+        },
       },
     },
-  },
-  {
-    id: 5290,
-    content: 'Conversation was marked resolved by John',
-    account_id: 1,
-    inbox_id: 475,
-    conversation_id: 43,
-    message_type: 2,
-    created_at: 1732196029,
-    updated_at: '2024-11-21T13:33:49.059Z',
-    private: false,
-    status: 'sent',
-    source_id: null,
-    content_type: 'text',
-    content_attributes: {},
-    sender_type: null,
-    sender_id: null,
-    external_source_ids: {},
-    additional_attributes: {},
-    processed_message_content: 'Conversation was marked resolved by John',
-    sentiment: {},
-    conversation: {
-      assignee_id: 1,
-      unread_count: 0,
-      last_activity_at: 1732196029,
-      contact_inbox: {
-        source_id: 'b018c554-8e17-4102-8a0b-f6d20d021017',
+    {
+      id: 5289,
+      content: 'John added delivery',
+      account_id: 1,
+      inbox_id: 475,
+      conversation_id: 43,
+      message_type: 2,
+      created_at: 1732196020,
+      updated_at: '2024-11-21T13:33:40.822Z',
+      private: false,
+      status: 'sent',
+      source_id: null,
+      content_type: 'text',
+      content_attributes: {},
+      sender_type: null,
+      sender_id: null,
+      external_source_ids: {},
+      additional_attributes: {},
+      processed_message_content: 'John added delivery',
+      sentiment: {},
+      conversation: {
+        assignee_id: 1,
+        unread_count: 0,
+        last_activity_at: 1732196020,
+        contact_inbox: {
+          source_id: 'b018c554-8e17-4102-8a0b-f6d20d021017',
+        },
       },
     },
-  },
-].map(camelcaseKeys);
+    {
+      id: 5290,
+      content: 'Conversation was marked resolved by John',
+      account_id: 1,
+      inbox_id: 475,
+      conversation_id: 43,
+      message_type: 2,
+      created_at: 1732196029,
+      updated_at: '2024-11-21T13:33:49.059Z',
+      private: false,
+      status: 'sent',
+      source_id: null,
+      content_type: 'text',
+      content_attributes: {},
+      sender_type: null,
+      sender_id: null,
+      external_source_ids: {},
+      additional_attributes: {},
+      processed_message_content: 'Conversation was marked resolved by John',
+      sentiment: {},
+      conversation: {
+        assignee_id: 1,
+        unread_count: 0,
+        last_activity_at: 1732196029,
+        contact_inbox: {
+          source_id: 'b018c554-8e17-4102-8a0b-f6d20d021017',
+        },
+      },
+    },
+  ],
+  { deep: true }
+);
 
 const shouldGroupWithNext = index => {
   if (index === messages.length - 1) return false;
@@ -718,6 +722,8 @@ const shouldGroupWithNext = index => {
   const current = messages[index];
   const next = messages[index + 1];
 
+  if (next.status === 'failed') return false;
+
   const nextSenderId = next.senderId ?? next.sender?.id;
   const currentSenderId = current.senderId ?? current.sender?.id;
   if (currentSenderId !== nextSenderId) return false;