diff --git a/app/controllers/api/v1/widget/conversations_controller.rb b/app/controllers/api/v1/widget/conversations_controller.rb
index 00e718614..b94fc0d90 100644
--- a/app/controllers/api/v1/widget/conversations_controller.rb
+++ b/app/controllers/api/v1/widget/conversations_controller.rb
@@ -1,6 +1,7 @@
 class Api::V1::Widget::ConversationsController < Api::V1::Widget::BaseController
   include Events::Types
-  before_action :render_not_found_if_empty, only: [:toggle_typing, :toggle_status, :set_custom_attributes, :destroy_custom_attributes]
+  before_action :render_not_found_if_empty,
+                only: [:toggle_typing, :toggle_status, :request_handoff, :set_custom_attributes, :destroy_custom_attributes]
 
   def index
     @conversation = conversation
@@ -64,6 +65,11 @@ class Api::V1::Widget::ConversationsController < Api::V1::Widget::BaseController
     head :ok
   end
 
+  def request_handoff
+    perform_handoff if conversation.pending?
+    head :ok
+  end
+
   def set_custom_attributes
     conversation.update!(custom_attributes: permitted_params[:custom_attributes])
   end
@@ -99,4 +105,40 @@ class Api::V1::Widget::ConversationsController < Api::V1::Widget::BaseController
                                                                message: [:content, :referer_url, :timestamp, :echo_id],
                                                                custom_attributes: {})
   end
+
+  def perform_handoff
+    assistant = captain_assistant
+    previous_executed_by = Current.executed_by
+    Current.executed_by = assistant if assistant
+
+    I18n.with_locale(conversation.account.locale) do
+      create_captain_handoff_message(assistant) if assistant
+      conversation.bot_handoff!
+      send_out_of_office_message_after_handoff
+    end
+  ensure
+    Current.executed_by = previous_executed_by
+  end
+
+  def captain_assistant
+    return unless inbox.respond_to?(:captain_assistant)
+
+    inbox.captain_assistant
+  end
+
+  def create_captain_handoff_message(assistant)
+    conversation.messages.create!(
+      message_type: :outgoing,
+      account_id: conversation.account_id,
+      inbox_id: conversation.inbox_id,
+      sender: assistant,
+      content: assistant.config['handoff_message'].presence || I18n.t('conversations.captain.handoff')
+    )
+  end
+
+  def send_out_of_office_message_after_handoff
+    return if conversation.campaign.present?
+
+    ::MessageTemplates::Template::OutOfOffice.perform_if_applicable(conversation)
+  end
 end
diff --git a/app/javascript/widget/api/conversation.js b/app/javascript/widget/api/conversation.js
index 05e81ff9f..588f68b87 100755
--- a/app/javascript/widget/api/conversation.js
+++ b/app/javascript/widget/api/conversation.js
@@ -62,6 +62,12 @@ const toggleStatus = async () => {
   );
 };
 
+const requestHandoff = async () => {
+  return API.post(
+    `/api/v1/widget/conversations/request_handoff${window.location.search}`
+  );
+};
+
 const setCustomAttributes = async customAttributes => {
   return API.post(
     `/api/v1/widget/conversations/set_custom_attributes${window.location.search}`,
@@ -90,6 +96,7 @@ export {
   setUserLastSeenAt,
   sendEmailTranscript,
   toggleStatus,
+  requestHandoff,
   setCustomAttributes,
   deleteCustomAttribute,
 };
diff --git a/app/javascript/widget/components/ChatFooter.vue b/app/javascript/widget/components/ChatFooter.vue
index c85727a2b..aa8fd4aa4 100755
--- a/app/javascript/widget/components/ChatFooter.vue
+++ b/app/javascript/widget/components/ChatFooter.vue
@@ -5,12 +5,15 @@ import CustomButton from 'shared/components/Button.vue';
 import FooterReplyTo from 'widget/components/FooterReplyTo.vue';
 import ChatInputWrap from 'widget/components/ChatInputWrap.vue';
 import { BUS_EVENTS } from 'shared/constants/busEvents';
+import { CONVERSATION_STATUS } from 'shared/constants/messages';
 import { sendEmailTranscript } from 'widget/api/conversation';
 import { useRouter } from 'vue-router';
 import { IFrameHelper } from '../helpers/utils';
 import { CHATWOOT_ON_START_CONVERSATION } from '../constants/sdkEvents';
 import { emitter } from 'shared/helpers/mitt';
 
+const CAPTAIN_HANDOFF_REPLY_THRESHOLD = 5;
+
 export default {
   components: {
     ChatInputWrap,
@@ -24,6 +27,7 @@ export default {
   data() {
     return {
       inReplyTo: null,
+      isRequestingHandoff: false,
     };
   },
   computed: {
@@ -31,6 +35,7 @@ export default {
       conversationAttributes: 'conversationAttributes/getConversationParams',
       widgetColor: 'appConfig/getWidgetColor',
       conversationSize: 'conversation/getConversationSize',
+      captainReplyCount: 'conversation/getCaptainReplyCount',
       currentUser: 'contacts/getCurrentUser',
       isWidgetStyleFlat: 'appConfig/isWidgetStyleFlat',
     }),
@@ -45,6 +50,12 @@ export default {
     showEmailTranscriptButton() {
       return this.hasEmail;
     },
+    showCaptainHandoffButton() {
+      return (
+        this.conversationAttributes.status === CONVERSATION_STATUS.PENDING &&
+        this.captainReplyCount >= CAPTAIN_HANDOFF_REPLY_THRESHOLD
+      );
+    },
     hasEmail() {
       return this.currentUser && this.currentUser.has_email;
     },
@@ -58,7 +69,11 @@ export default {
     emitter.on(BUS_EVENTS.TOGGLE_REPLY_TO_MESSAGE, this.toggleReplyTo);
   },
   methods: {
-    ...mapActions('conversation', ['sendMessage', 'sendAttachment']),
+    ...mapActions('conversation', [
+      'sendMessage',
+      'sendAttachment',
+      'requestHandoff',
+    ]),
     ...mapActions('conversationAttributes', ['getAttributes']),
     async handleSendMessage(content) {
       await this.sendMessage({
@@ -90,6 +105,18 @@ export default {
     toggleReplyTo(message) {
       this.inReplyTo = message;
     },
+    async handleRequestHandoff() {
+      try {
+        this.isRequestingHandoff = true;
+        await this.requestHandoff();
+      } catch (error) {
+        emitter.emit(BUS_EVENTS.SHOW_ALERT, {
+          message: this.$t('CAPTAIN_HANDOFF.ERROR'),
+        });
+      } finally {
+        this.isRequestingHandoff = false;
+      }
+    },
     async sendTranscript() {
       if (this.hasEmail) {
         try {
@@ -124,6 +151,17 @@ export default {
       :in-reply-to="inReplyTo"
       @dismiss="inReplyTo = null"
     />
+    <CustomButton
+      v-if="showCaptainHandoffButton"
+      block
+      class="mb-2 font-medium"
+      :bg-color="widgetColor"
+      :text-color="textColor"
+      :disabled="isRequestingHandoff"
+      @click="handleRequestHandoff"
+    >
+      {{ $t('CAPTAIN_HANDOFF.BUTTON_TEXT') }}
+    </CustomButton>
     <ChatInputWrap
       class="shadow-sm"
       :on-send-message="handleSendMessage"
diff --git a/app/javascript/widget/i18n/locale/en.json b/app/javascript/widget/i18n/locale/en.json
index c3d6ddfc1..094b58884 100644
--- a/app/javascript/widget/i18n/locale/en.json
+++ b/app/javascript/widget/i18n/locale/en.json
@@ -47,6 +47,10 @@
   "CONTINUE_CONVERSATION": "Continue conversation",
   "YOU": "You",
   "START_NEW_CONVERSATION": "Start a new conversation",
+  "CAPTAIN_HANDOFF": {
+    "BUTTON_TEXT": "Talk to a support agent",
+    "ERROR": "Could not request a handoff, please try again"
+  },
   "VIEW_UNREAD_MESSAGES": "You have unread messages",
   "UNREAD_VIEW": {
     "VIEW_MESSAGES_BUTTON": "See new messages",
diff --git a/app/javascript/widget/store/modules/conversation/actions.js b/app/javascript/widget/store/modules/conversation/actions.js
index aa08af615..69c8ebc1a 100644
--- a/app/javascript/widget/store/modules/conversation/actions.js
+++ b/app/javascript/widget/store/modules/conversation/actions.js
@@ -6,6 +6,7 @@ import {
   toggleTyping,
   setUserLastSeenAt,
   toggleStatus,
+  requestHandoff,
   setCustomAttributes,
   deleteCustomAttribute,
 } from 'widget/api/conversation';
@@ -212,6 +213,11 @@ export const actions = {
     await toggleStatus();
   },
 
+  requestHandoff: async ({ dispatch }) => {
+    await requestHandoff();
+    dispatch('conversationAttributes/getAttributes', {}, { root: true });
+  },
+
   setCustomAttributes: async (
     { commit, rootGetters },
     customAttributes = {}
diff --git a/app/javascript/widget/store/modules/conversation/getters.js b/app/javascript/widget/store/modules/conversation/getters.js
index ef1cd1cc3..a74ac45e1 100644
--- a/app/javascript/widget/store/modules/conversation/getters.js
+++ b/app/javascript/widget/store/modules/conversation/getters.js
@@ -39,6 +39,15 @@ export const getters = {
   getMessageCount: _state => {
     return Object.values(_state.conversations).length;
   },
+  getCaptainReplyCount: _state => {
+    return Object.values(_state.conversations).filter(message => {
+      const { message_type: messageType, sender = {} } = message;
+      return (
+        messageType === MESSAGE_TYPE.OUTGOING &&
+        sender.type === 'captain_assistant'
+      );
+    }).length;
+  },
   getUnreadMessageCount: _state => {
     const { userLastSeenAt } = _state.meta;
     return Object.values(_state.conversations).filter(chat => {
diff --git a/config/routes.rb b/config/routes.rb
index eff17e714..6c74d0b2d 100644
--- a/config/routes.rb
+++ b/config/routes.rb
@@ -419,6 +419,7 @@ Rails.application.routes.draw do
             post :update_last_seen
             post :toggle_typing
             post :transcript
+            post :request_handoff
             get  :toggle_status
           end
         end