diff --git a/app/javascript/dashboard/api/inbox/message.js b/app/javascript/dashboard/api/inbox/message.js
index 6cb885e3d..8f294a0ee 100644
--- a/app/javascript/dashboard/api/inbox/message.js
+++ b/app/javascript/dashboard/api/inbox/message.js
@@ -86,6 +86,12 @@ class MessageApi extends ApiClient {
     return axios.delete(`${this.url}/${conversationID}/messages/${messageId}`);
   }
 
+  retry(conversationID, messageId) {
+    return axios.post(
+      `${this.url}/${conversationID}/messages/${messageId}/retry`
+    );
+  }
+
   getPreviousMessages({ conversationId, after, before }) {
     const params = { before };
     if (after && Number(after) !== Number(before)) {
diff --git a/app/javascript/dashboard/components/widgets/conversation/Message.vue b/app/javascript/dashboard/components/widgets/conversation/Message.vue
index d7c9742ae..34ad5f59f 100644
--- a/app/javascript/dashboard/components/widgets/conversation/Message.vue
+++ b/app/javascript/dashboard/components/widgets/conversation/Message.vue
@@ -1,7 +1,7 @@
 <template>
   <li v-if="shouldRenderMessage" :id="`message${data.id}`" :class="alignBubble">
     <div :class="wrapClass">
-      <div v-if="isFailed" class="message-failed--alert">
+      <div v-if="isFailed && !hasOneDayPassed" class="message-failed--alert">
         <woot-button
           v-tooltip.top-end="$t('CONVERSATION.TRY_AGAIN')"
           size="tiny"
@@ -148,6 +148,7 @@ import { BUS_EVENTS } from 'shared/constants/busEvents';
 import { ACCOUNT_EVENTS } from 'dashboard/helper/AnalyticsHelper/events';
 import { LOCAL_STORAGE_KEYS } from 'dashboard/constants/localStorage';
 import { LocalStorage } from 'shared/helpers/localStorage';
+import { getDayDifferenceFromNow } from 'shared/helpers/DateHelper';
 
 export default {
   components: {
@@ -209,6 +210,10 @@ export default {
         created_at: this.data.created_at || '',
       }));
     },
+    hasOneDayPassed() {
+      // Disable retry button if the message is failed and the message is older than 24 hours
+      return getDayDifferenceFromNow(new Date(), this.data?.created_at) >= 1;
+    },
     shouldRenderMessage() {
       return (
         this.hasAttachments ||
diff --git a/app/javascript/dashboard/store/modules/conversations/actions.js b/app/javascript/dashboard/store/modules/conversations/actions.js
index 41516bcd6..6bf5501ad 100644
--- a/app/javascript/dashboard/store/modules/conversations/actions.js
+++ b/app/javascript/dashboard/store/modules/conversations/actions.js
@@ -11,6 +11,19 @@ import {
 } from './helpers/actionHelpers';
 import messageReadActions from './actions/messageReadActions';
 import messageTranslateActions from './actions/messageTranslateActions';
+
+export const hasMessageFailedWithExternalError = pendingMessage => {
+  // This helper is used to check if the message has failed with an external error.
+  // We have two cases
+  // 1. Messages that fail from the UI itself (due to large attachments or a failed network):
+  //    In this case, the message will have a status of failed but no external error. So we need to create that message again
+  // 2. Messages sent from Chatwoot but failed to deliver to the customer for some reason (user blocking or client system down):
+  //    In this case, the message will have a status of failed and an external error. So we need to retry that message
+  const { content_attributes: contentAttributes, status } = pendingMessage;
+  const externalError = contentAttributes?.external_error ?? '';
+  return status === MESSAGE_STATUS.FAILED && externalError !== '';
+};
+
 // actions
 const actions = {
   getConversation: async ({ commit }, conversationId) => {
@@ -242,12 +255,15 @@ const actions = {
   },
 
   sendMessageWithData: async ({ commit }, pendingMessage) => {
+    const { conversation_id: conversationId, id } = pendingMessage;
     try {
       commit(types.ADD_MESSAGE, {
         ...pendingMessage,
         status: MESSAGE_STATUS.PROGRESS,
       });
-      const response = await MessageApi.create(pendingMessage);
+      const response = hasMessageFailedWithExternalError(pendingMessage)
+        ? await MessageApi.retry(conversationId, id)
+        : await MessageApi.create(pendingMessage);
       commit(types.ADD_MESSAGE, {
         ...response.data,
         status: MESSAGE_STATUS.SENT,
diff --git a/app/javascript/dashboard/store/modules/specs/conversations/actions.spec.js b/app/javascript/dashboard/store/modules/specs/conversations/actions.spec.js
index 5ff27c03e..0b375a543 100644
--- a/app/javascript/dashboard/store/modules/specs/conversations/actions.spec.js
+++ b/app/javascript/dashboard/store/modules/specs/conversations/actions.spec.js
@@ -1,5 +1,7 @@
 import axios from 'axios';
-import actions from '../../conversations/actions';
+import actions, {
+  hasMessageFailedWithExternalError,
+} from '../../conversations/actions';
 import types from '../../../mutation-types';
 const dataToSend = {
   payload: [
@@ -18,6 +20,41 @@ const dispatch = jest.fn();
 global.axios = axios;
 jest.mock('axios');
 
+describe('#hasMessageFailedWithExternalError', () => {
+  it('returns false if message is sent', () => {
+    const pendingMessage = {
+      status: 'sent',
+      content_attributes: {},
+    };
+    expect(hasMessageFailedWithExternalError(pendingMessage)).toBe(false);
+  });
+  it('returns false if status is not failed', () => {
+    const pendingMessage = {
+      status: 'progress',
+      content_attributes: {},
+    };
+    expect(hasMessageFailedWithExternalError(pendingMessage)).toBe(false);
+  });
+
+  it('returns false if status is failed but no external error', () => {
+    const pendingMessage = {
+      status: 'failed',
+      content_attributes: {},
+    };
+    expect(hasMessageFailedWithExternalError(pendingMessage)).toBe(false);
+  });
+
+  it('returns true if status is failed and has external error', () => {
+    const pendingMessage = {
+      status: 'failed',
+      content_attributes: {
+        external_error: 'error',
+      },
+    };
+    expect(hasMessageFailedWithExternalError(pendingMessage)).toBe(true);
+  });
+});
+
 describe('#actions', () => {
   describe('#getConversation', () => {
     it('sends correct actions if API is success', async () => {
diff --git a/app/javascript/shared/helpers/DateHelper.js b/app/javascript/shared/helpers/DateHelper.js
index dcff6e4c5..dc6b8b4fd 100644
--- a/app/javascript/shared/helpers/DateHelper.js
+++ b/app/javascript/shared/helpers/DateHelper.js
@@ -2,7 +2,7 @@ import fromUnixTime from 'date-fns/fromUnixTime';
 import format from 'date-fns/format';
 import isToday from 'date-fns/isToday';
 import isYesterday from 'date-fns/isYesterday';
-import { endOfDay, getUnixTime, startOfDay } from 'date-fns';
+import { endOfDay, getUnixTime, startOfDay, differenceInDays } from 'date-fns';
 
 export const formatUnixDate = (date, dateFormat = 'MMM dd, yyyy') => {
   const unixDate = fromUnixTime(date);
@@ -45,3 +45,8 @@ export const generateRelativeTime = (value, unit, languageCode) => {
   });
   return rtf.format(value, unit);
 };
+
+export const getDayDifferenceFromNow = (now, timestampInSeconds) => {
+  const date = new Date(timestampInSeconds * 1000);
+  return differenceInDays(now, date);
+};
diff --git a/app/javascript/shared/helpers/specs/DateHelper.spec.js b/app/javascript/shared/helpers/specs/DateHelper.spec.js
index ee2e3ef67..63ef9edd8 100644
--- a/app/javascript/shared/helpers/specs/DateHelper.spec.js
+++ b/app/javascript/shared/helpers/specs/DateHelper.spec.js
@@ -4,6 +4,7 @@ import {
   formatDigitToString,
   isTimeAfter,
   generateRelativeTime,
+  getDayDifferenceFromNow,
 } from '../DateHelper';
 
 describe('#DateHelper', () => {
@@ -120,3 +121,25 @@ describe('generateRelativeTime', () => {
     expect(actualResult).toBe(expectedResult);
   });
 });
+
+describe('#getDayDifferenceFromNow', () => {
+  it('should return the difference if in same day', () => {
+    const now = new Date('2023-12-08T00:00:00.000Z');
+    const timestampInSeconds = 1702020305; // 08/12/2023, 12:55:05 (GMT+05:30)
+    const expectedResult = 0;
+
+    const actualResult = getDayDifferenceFromNow(now, timestampInSeconds);
+
+    expect(actualResult).toBe(expectedResult);
+  });
+
+  it('should return the difference if in different day', () => {
+    const now = new Date('2023-12-11T00:00:00.000Z');
+    const timestampInSeconds = 1702020305; // 08/12/2023, 12:55:05 (GMT+05:30)
+    const expectedResult = 2;
+
+    const actualResult = getDayDifferenceFromNow(now, timestampInSeconds);
+
+    expect(actualResult).toBe(expectedResult);
+  });
+});