diff --git a/app/javascript/dashboard/components-next/message/Message.vue b/app/javascript/dashboard/components-next/message/Message.vue
index 586a4b4cb..dd655d0cc 100644
--- a/app/javascript/dashboard/components-next/message/Message.vue
+++ b/app/javascript/dashboard/components-next/message/Message.vue
@@ -131,6 +131,8 @@ const props = defineProps({
   sourceId: { type: String, default: '' }, // eslint-disable-line vue/no-unused-properties
 });
 
+const emit = defineEmits(['retry']);
+
 const contextMenuPosition = ref({});
 const showBackgroundHighlight = ref(false);
 const showContextMenu = ref(false);
@@ -524,6 +526,7 @@ provideMessageContext({
         class="[grid-area:meta]"
         :class="flexOrientationClass"
         :error="contentAttributes.externalError"
+        @retry="emit('retry')"
       />
     </div>
     <div v-if="shouldShowContextMenu" class="context-menu-wrap">
diff --git a/app/javascript/dashboard/components-next/message/MessageError.vue b/app/javascript/dashboard/components-next/message/MessageError.vue
index d3a03e746..cd17c1e3f 100644
--- a/app/javascript/dashboard/components-next/message/MessageError.vue
+++ b/app/javascript/dashboard/components-next/message/MessageError.vue
@@ -1,16 +1,22 @@
 <script setup>
+import { computed } from 'vue';
 import Icon from 'next/icon/Icon.vue';
 import { useI18n } from 'vue-i18n';
 import { useMessageContext } from './provider.js';
-import { ORIENTATION } from './constants';
+import { hasOneDayPassed } from 'shared/helpers/timeHelper';
+import { ORIENTATION, MESSAGE_STATUS } from './constants';
 
 defineProps({
   error: { type: String, required: true },
 });
 
-const { orientation } = useMessageContext();
+const emit = defineEmits(['retry']);
+
+const { orientation, status, createdAt } = useMessageContext();
 
 const { t } = useI18n();
+
+const canRetry = computed(() => !hasOneDayPassed(createdAt.value));
 </script>
 
 <template>
@@ -35,5 +41,14 @@ const { t } = useI18n();
         {{ error }}
       </div>
     </div>
+    <button
+      v-if="canRetry"
+      type="button"
+      :disabled="status !== MESSAGE_STATUS.FAILED"
+      class="bg-n-alpha-2 rounded-md size-5 grid place-content-center cursor-pointer"
+      @click="emit('retry')"
+    >
+      <Icon icon="i-lucide-refresh-ccw" class="text-n-ruby-11 size-[14px]" />
+    </button>
   </div>
 </template>
diff --git a/app/javascript/dashboard/components-next/message/MessageList.vue b/app/javascript/dashboard/components-next/message/MessageList.vue
index 44b317c56..4c4fe1a1d 100644
--- a/app/javascript/dashboard/components-next/message/MessageList.vue
+++ b/app/javascript/dashboard/components-next/message/MessageList.vue
@@ -37,6 +37,8 @@ const props = defineProps({
   },
 });
 
+const emit = defineEmits(['retry']);
+
 const allMessages = computed(() => {
   return useCamelCase(props.messages, { deep: true });
 });
@@ -113,6 +115,7 @@ const getInReplyToMessage = parentMessage => {
         :inbox-supports-reply-to="inboxSupportsReplyTo"
         :current-user-id="currentUserId"
         data-clarity-mask="True"
+        @retry="emit('retry', message)"
       />
     </template>
     <slot name="after" />
diff --git a/app/javascript/dashboard/components/widgets/conversation/MessagesView.vue b/app/javascript/dashboard/components/widgets/conversation/MessagesView.vue
index 1f850cd74..3cb46c05f 100644
--- a/app/javascript/dashboard/components/widgets/conversation/MessagesView.vue
+++ b/app/javascript/dashboard/components/widgets/conversation/MessagesView.vue
@@ -4,6 +4,7 @@ import { ref, provide } from 'vue';
 import { useConfig } from 'dashboard/composables/useConfig';
 import { useKeyboardEvents } from 'dashboard/composables/useKeyboardEvents';
 import { useAI } from 'dashboard/composables/useAI';
+import { useSnakeCase } from 'dashboard/composables/useTransformKeys';
 
 // components
 import ReplyBox from './ReplyBox.vue';
@@ -437,6 +438,11 @@ export default {
     makeMessagesRead() {
       this.$store.dispatch('markMessagesRead', { id: this.currentChat.id });
     },
+    async handleMessageRetry(message) {
+      if (!message) return;
+      const payload = useSnakeCase(message);
+      await this.$store.dispatch('sendMessageWithData', payload);
+    },
   },
 };
 </script>
@@ -465,6 +471,7 @@ export default {
       :is-an-email-channel="isAnEmailChannel"
       :inbox-supports-reply-to="inboxSupportsReplyTo"
       :messages="getMessages"
+      @retry="handleMessageRetry"
     >
       <template #beforeAll>
         <transition name="slide-up">
diff --git a/app/javascript/shared/helpers/specs/timeHelper.spec.js b/app/javascript/shared/helpers/specs/timeHelper.spec.js
index 13d04568f..e7a4e025f 100644
--- a/app/javascript/shared/helpers/specs/timeHelper.spec.js
+++ b/app/javascript/shared/helpers/specs/timeHelper.spec.js
@@ -4,6 +4,8 @@ import {
   dynamicTime,
   dateFormat,
   shortTimestamp,
+  getDayDifferenceFromNow,
+  hasOneDayPassed,
 } from 'shared/helpers/timeHelper';
 
 beforeEach(() => {
@@ -90,3 +92,148 @@ describe('#shortTimestamp', () => {
     expect(shortTimestamp('4 years ago', true)).toEqual('4y ago');
   });
 });
+
+describe('#getDayDifferenceFromNow', () => {
+  it('returns 0 for timestamps from today', () => {
+    // Mock current date: May 5, 2023
+    const now = new Date(Date.UTC(2023, 4, 5, 12, 0, 0)); // 12:00 PM
+    const todayTimestamp = Math.floor(now.getTime() / 1000); // Same day
+
+    expect(getDayDifferenceFromNow(now, todayTimestamp)).toEqual(0);
+  });
+
+  it('returns 2 for timestamps from 2 days ago', () => {
+    const now = new Date(Date.UTC(2023, 4, 5, 12, 0, 0)); // May 5, 2023
+    const twoDaysAgoTimestamp = Math.floor(
+      new Date(Date.UTC(2023, 4, 3, 10, 0, 0)).getTime() / 1000
+    ); // May 3, 2023
+
+    expect(getDayDifferenceFromNow(now, twoDaysAgoTimestamp)).toEqual(2);
+  });
+
+  it('returns 7 for timestamps from a week ago', () => {
+    const now = new Date(Date.UTC(2023, 4, 5, 12, 0, 0)); // May 5, 2023
+    const weekAgoTimestamp = Math.floor(
+      new Date(Date.UTC(2023, 3, 28, 8, 0, 0)).getTime() / 1000
+    ); // April 28, 2023
+
+    expect(getDayDifferenceFromNow(now, weekAgoTimestamp)).toEqual(7);
+  });
+
+  it('returns 30 for timestamps from a month ago', () => {
+    const now = new Date(Date.UTC(2023, 4, 5, 12, 0, 0)); // May 5, 2023
+    const monthAgoTimestamp = Math.floor(
+      new Date(Date.UTC(2023, 3, 5, 12, 0, 0)).getTime() / 1000
+    ); // April 5, 2023
+
+    expect(getDayDifferenceFromNow(now, monthAgoTimestamp)).toEqual(30);
+  });
+
+  it('handles edge case with different times on same day', () => {
+    const now = new Date(Date.UTC(2023, 4, 5, 23, 59, 59)); // May 5, 2023 11:59:59 PM
+    const morningTimestamp = Math.floor(
+      new Date(Date.UTC(2023, 4, 5, 0, 0, 1)).getTime() / 1000
+    ); // May 5, 2023 12:00:01 AM
+
+    expect(getDayDifferenceFromNow(now, morningTimestamp)).toEqual(0);
+  });
+
+  it('handles cross-month boundaries correctly', () => {
+    const now = new Date(Date.UTC(2023, 4, 1, 12, 0, 0)); // May 1, 2023
+    const lastMonthTimestamp = Math.floor(
+      new Date(Date.UTC(2023, 3, 30, 12, 0, 0)).getTime() / 1000
+    ); // April 30, 2023
+
+    expect(getDayDifferenceFromNow(now, lastMonthTimestamp)).toEqual(1);
+  });
+
+  it('handles cross-year boundaries correctly', () => {
+    const now = new Date(Date.UTC(2023, 0, 2, 12, 0, 0)); // January 2, 2023
+    const lastYearTimestamp = Math.floor(
+      new Date(Date.UTC(2022, 11, 31, 12, 0, 0)).getTime() / 1000
+    ); // December 31, 2022
+
+    expect(getDayDifferenceFromNow(now, lastYearTimestamp)).toEqual(2);
+  });
+});
+
+describe('#hasOneDayPassed', () => {
+  beforeEach(() => {
+    // Mock current date: May 5, 2023, 12:00 PM UTC (1683288000)
+    const mockDate = new Date(1683288000 * 1000);
+    vi.setSystemTime(mockDate);
+  });
+
+  it('returns false for timestamps from today', () => {
+    // Same day, different time - May 5, 2023 8:00 AM UTC
+    const todayTimestamp = 1683273600;
+
+    expect(hasOneDayPassed(todayTimestamp)).toBe(false);
+  });
+
+  it('returns false for timestamps from yesterday (less than 24 hours)', () => {
+    // Yesterday but less than 24 hours ago - May 4, 2023 6:00 PM UTC (18 hours ago)
+    const yesterdayTimestamp = 1683230400;
+
+    expect(hasOneDayPassed(yesterdayTimestamp)).toBe(false);
+  });
+
+  it('returns true for timestamps from exactly 1 day ago', () => {
+    // Exactly 24 hours ago - May 4, 2023 12:00 PM UTC
+    const oneDayAgoTimestamp = 1683201600;
+
+    expect(hasOneDayPassed(oneDayAgoTimestamp)).toBe(true);
+  });
+
+  it('returns true for timestamps from more than 1 day ago', () => {
+    // 2 days ago - May 3, 2023 10:00 AM UTC
+    const twoDaysAgoTimestamp = 1683108000;
+
+    expect(hasOneDayPassed(twoDaysAgoTimestamp)).toBe(true);
+  });
+
+  it('returns true for timestamps from a week ago', () => {
+    // 7 days ago - April 28, 2023 8:00 AM UTC
+    const weekAgoTimestamp = 1682668800;
+
+    expect(hasOneDayPassed(weekAgoTimestamp)).toBe(true);
+  });
+
+  it('returns true for null timestamp (defensive check)', () => {
+    expect(hasOneDayPassed(null)).toBe(true);
+  });
+
+  it('returns true for undefined timestamp (defensive check)', () => {
+    expect(hasOneDayPassed(undefined)).toBe(true);
+  });
+
+  it('returns true for zero timestamp (defensive check)', () => {
+    expect(hasOneDayPassed(0)).toBe(true);
+  });
+
+  it('returns true for empty string timestamp (defensive check)', () => {
+    expect(hasOneDayPassed('')).toBe(true);
+  });
+
+  it('handles cross-month boundaries correctly', () => {
+    // Set current time to May 1, 2023 12:00 PM UTC (1682942400)
+    const mayFirst = new Date(1682942400 * 1000);
+    vi.setSystemTime(mayFirst);
+
+    // April 29, 2023 12:00 PM UTC (1682769600) - 2 days ago, crossing month boundary
+    const crossMonthTimestamp = 1682769600;
+
+    expect(hasOneDayPassed(crossMonthTimestamp)).toBe(true);
+  });
+
+  it('handles cross-year boundaries correctly', () => {
+    // Set current time to January 2, 2023 12:00 PM UTC (1672660800)
+    const newYear = new Date(1672660800 * 1000);
+    vi.setSystemTime(newYear);
+
+    // December 30, 2022 12:00 PM UTC (1672401600) - 3 days ago, crossing year boundary
+    const crossYearTimestamp = 1672401600;
+
+    expect(hasOneDayPassed(crossYearTimestamp)).toBe(true);
+  });
+});
diff --git a/app/javascript/shared/helpers/timeHelper.js b/app/javascript/shared/helpers/timeHelper.js
index 6e041c7ec..5347d2410 100644
--- a/app/javascript/shared/helpers/timeHelper.js
+++ b/app/javascript/shared/helpers/timeHelper.js
@@ -3,6 +3,7 @@ import {
   isSameYear,
   fromUnixTime,
   formatDistanceToNow,
+  differenceInDays,
 } from 'date-fns';
 
 /**
@@ -91,3 +92,25 @@ export const shortTimestamp = (time, withAgo = false) => {
     .replace(' years ago', `y${suffix}`);
   return convertToShortTime;
 };
+
+/**
+ * Calculates the difference in days between now and a given timestamp.
+ * @param {Date} now - Current date/time.
+ * @param {number} timestampInSeconds - Unix timestamp in seconds.
+ * @returns {number} Number of days difference.
+ */
+export const getDayDifferenceFromNow = (now, timestampInSeconds) => {
+  const date = new Date(timestampInSeconds * 1000);
+  return differenceInDays(now, date);
+};
+
+/**
+ * Checks if more than 24 hours have passed since a given timestamp.
+ * Useful for determining if retry/refresh actions should be disabled.
+ * @param {number} timestamp - Unix timestamp.
+ * @returns {boolean} True if more than 24 hours have passed.
+ */
+export const hasOneDayPassed = timestamp => {
+  if (!timestamp) return true; // Defensive check
+  return getDayDifferenceFromNow(new Date(), timestamp) >= 1;
+};