Revert "feat: Add support for image files in Captain (#11730 )"

This reverts commit 811eb66615.
fix: Reply time calculation for re-opened conversations (#11787 )
2025-06-28 16:54:24 -07:00 · 2025-06-27 10:48:07 +05:30 · 2025-06-26 19:16:06 +05:30
39 changed files with 806 additions and 690 deletions
@@ -0,0 +1,14 @@
+class Api::V1::Accounts::Integrations::NotionController < Api::V1::Accounts::BaseController
+  before_action :fetch_hook, only: [:destroy]
+
+  def destroy
+    @hook.destroy!
+    head :ok
+  end
+
+  private
+
+  def fetch_hook
+    @hook = Integrations::Hook.where(account: Current.account).find_by(app_id: 'notion')
+  end
+end
@@ -0,0 +1,21 @@
+class Api::V1::Accounts::Notion::AuthorizationsController < Api::V1::Accounts::OauthAuthorizationController
+  include NotionConcern
+
+  def create
+    redirect_url = notion_client.auth_code.authorize_url(
+      {
+        redirect_uri: "#{base_url}/notion/callback",
+        response_type: 'code',
+        owner: 'user',
+        state: state,
+        client_id: GlobalConfigService.load('NOTION_CLIENT_ID', nil)
+      }
+    )
+
+    if redirect_url
+      render json: { success: true, url: redirect_url }
+    else
+      render json: { success: false }, status: :unprocessable_entity
+    end
+  end
+end
@@ -0,0 +1,21 @@
+module NotionConcern
+  extend ActiveSupport::Concern
+
+  def notion_client
+    app_id = GlobalConfigService.load('NOTION_CLIENT_ID', nil)
+    app_secret = GlobalConfigService.load('NOTION_CLIENT_SECRET', nil)
+
+    ::OAuth2::Client.new(app_id, app_secret, {
+                           site: 'https://api.notion.com',
+                           authorize_url: 'https://api.notion.com/v1/oauth/authorize',
+                           token_url: 'https://api.notion.com/v1/oauth/token',
+                           auth_scheme: :basic_auth
+                         })
+  end
+
+  private
+
+  def scope
+    ''
+  end
+end
@@ -0,0 +1,36 @@
+class Notion::CallbacksController < OauthCallbackController
+  include NotionConcern
+
+  private
+
+  def provider_name
+    'notion'
+  end
+
+  def oauth_client
+    notion_client
+  end
+
+  def handle_response
+    hook = account.hooks.new(
+      access_token: parsed_body['access_token'],
+      status: 'enabled',
+      app_id: 'notion',
+      settings: {
+        token_type: parsed_body['token_type'],
+        workspace_name: parsed_body['workspace_name'],
+        workspace_id: parsed_body['workspace_id'],
+        workspace_icon: parsed_body['workspace_icon'],
+        bot_id: parsed_body['bot_id'],
+        owner: parsed_body['owner']
+      }
+    )
+
+    hook.save!
+    redirect_to notion_redirect_uri
+  end
+
+  def notion_redirect_uri
+    "#{ENV.fetch('FRONTEND_URL', nil)}/app/accounts/#{account.id}/settings/integrations/notion"
+  end
+end
@@ -39,6 +39,7 @@ class SuperAdmin::AppConfigsController < SuperAdmin::ApplicationController
      'email' => ['MAILER_INBOUND_EMAIL_DOMAIN'],
      'linear' => %w[LINEAR_CLIENT_ID LINEAR_CLIENT_SECRET],
      'slack' => %w[SLACK_CLIENT_ID SLACK_CLIENT_SECRET],
+      'notion' => %w[NOTION_CLIENT_ID NOTION_CLIENT_SECRET],
      'instagram' => %w[INSTAGRAM_APP_ID INSTAGRAM_APP_SECRET INSTAGRAM_VERIFY_TOKEN INSTAGRAM_API_VERSION ENABLE_INSTAGRAM_CHANNEL_HUMAN_AGENT]
    }

@@ -0,0 +1,14 @@
+/* global axios */
+import ApiClient from './ApiClient';
+
+class NotionOAuthClient extends ApiClient {
+  constructor() {
+    super('notion', { accountScoped: true });
+  }
+
+  generateAuthorization() {
+    return axios.post(`${this.url}/authorization`);
+  }
+}
+
+export default new NotionOAuthClient();
@@ -328,6 +328,14 @@
        "DESCRIPTION": "Linear workspace is not connected. Click the button below to connect your workspace to use this integration.",
        "BUTTON_TEXT": "Connect Linear workspace"
      }
+    },
+    "NOTION": {
+      "DELETE": {
+        "TITLE": "Are you sure you want to delete the Notion integration?",
+        "MESSAGE": "Deleting this integration will remove access to your Notion workspace and stop all related functionality.",
+        "CONFIRM": "Yes, delete",
+        "CANCEL": "Cancel"
+      }
    }
  },
  "CAPTAIN": {
@@ -0,0 +1,80 @@
+<script setup>
+import { ref, computed, onMounted } from 'vue';
+import {
+  useFunctionGetter,
+  useMapGetter,
+  useStore,
+} from 'dashboard/composables/store';
+import { useI18n } from 'vue-i18n';
+
+import ButtonNext from 'next/button/Button.vue';
+import notionClient from 'dashboard/api/notion_auth.js';
+
+import Integration from './Integration.vue';
+import Spinner from 'shared/components/Spinner.vue';
+
+const { t } = useI18n();
+const store = useStore();
+const integrationLoaded = ref(false);
+
+const integration = useFunctionGetter('integrations/getIntegration', 'notion');
+
+const uiFlags = useMapGetter('integrations/getUIFlags');
+
+const integrationAction = computed(() => {
+  if (integration.value.enabled) {
+    return 'disconnect';
+  }
+
+  return '';
+});
+
+const authorize = async () => {
+  const response = await notionClient.generateAuthorization();
+  const {
+    data: { url },
+  } = response;
+
+  window.location.href = url;
+};
+
+const initializeNotionIntegration = async () => {
+  await store.dispatch('integrations/get', 'notion');
+  integrationLoaded.value = true;
+};
+
+onMounted(() => {
+  initializeNotionIntegration();
+});
+</script>
+
+<template>
+  <div class="flex-grow flex-shrink p-4 overflow-auto mx-auto">
+    <div v-if="integrationLoaded && !uiFlags.isCreatingNotion">
+      <Integration
+        :integration-id="integration.id"
+        :integration-logo="integration.logo"
+        :integration-name="integration.name"
+        :integration-description="integration.description"
+        :integration-enabled="integration.enabled"
+        :integration-action="integrationAction"
+        :delete-confirmation-text="{
+          title: t('INTEGRATION_SETTINGS.NOTION.DELETE.TITLE'),
+          message: t('INTEGRATION_SETTINGS.NOTION.DELETE.MESSAGE'),
+        }"
+      >
+        <template #action>
+          <ButtonNext
+            faded
+            blue
+            :label="t('INTEGRATION_SETTINGS.CONNECT.BUTTON_TEXT')"
+            @click="authorize"
+          />
+        </template>
+      </Integration>
+    </div>
+    <div v-else class="flex items-center justify-center flex-1">
+      <Spinner size="" color-scheme="primary" />
+    </div>
+  </div>
+</template>
@@ -8,6 +8,7 @@ import DashboardApps from './DashboardApps/Index.vue';
 import Slack from './Slack.vue';
 import SettingsContent from '../Wrapper.vue';
 import Linear from './Linear.vue';
+import Notion from './Notion.vue';
 import Shopify from './Shopify.vue';

 export default {
@@ -90,6 +91,15 @@ export default {
          },
          props: route => ({ code: route.query.code }),
        },
+        {
+          path: 'notion',
+          name: 'settings_integrations_notion',
+          component: Notion,
+          meta: {
+            permissions: ['administrator'],
+          },
+          props: route => ({ code: route.query.code }),
+        },
        {
          path: 'shopify',
          name: 'settings_integrations_shopify',
@@ -47,6 +47,10 @@ class ReportingEventListener < BaseListener
    message = extract_message_and_account(event)[0]
    conversation = message.conversation
    waiting_since = event.data[:waiting_since]
+
+    return if waiting_since.blank?
+
+    # When waiting_since is nil, set reply_time to 0
    reply_time = message.created_at.to_i - waiting_since.to_i

    reporting_event = ReportingEvent.new(
@@ -198,11 +198,21 @@ class Conversation < ApplicationRecord
  private

  def execute_after_update_commit_callbacks
+    handle_resolved_status_change
    notify_status_change
    create_activity
    notify_conversation_updation
  end

+  def handle_resolved_status_change
+    # When conversation is resolved, clear waiting_since using update_column to avoid callbacks
+    return unless saved_change_to_status? && status == 'resolved'
+
+    # rubocop:disable Rails/SkipsModelValidations
+    update_column(:waiting_since, nil)
+    # rubocop:enable Rails/SkipsModelValidations
+  end
+
  def ensure_snooze_until_reset
    self.snoozed_until = nil unless snoozed?
  end
@@ -55,9 +55,11 @@ class Integrations::App
    when 'linear'
      GlobalConfigService.load('LINEAR_CLIENT_ID', nil).present?
    when 'shopify'
-      account.feature_enabled?('shopify_integration') && GlobalConfigService.load('SHOPIFY_CLIENT_ID', nil).present?
+      shopify_enabled?(account)
    when 'leadsquared'
      account.feature_enabled?('crm_integration')
+    when 'notion'
+      notion_enabled?(account)
    else
      true
    end
@@ -113,4 +115,14 @@ class Integrations::App
      all.detect { |app| app.id == params[:id] }
    end
  end
+
+  private
+
+  def shopify_enabled?(account)
+    account.feature_enabled?('shopify_integration') && GlobalConfigService.load('SHOPIFY_CLIENT_ID', nil).present?
+  end
+
+  def notion_enabled?(account)
+    account.feature_enabled?('notion_integration') && GlobalConfigService.load('NOTION_CLIENT_ID', nil).present?
+  end
 end
@@ -53,6 +53,10 @@ class Integrations::Hook < ApplicationRecord
    app_id == 'dialogflow'
  end

+  def notion?
+    app_id == 'notion'
+  end
+
  def disable
    update(status: 'disabled')
  end
@@ -156,9 +156,14 @@
    <path d="M 8 3 C 5.243 3 3 5.243 3 8 L 3 16 C 3 18.757 5.243 21 8 21 L 16 21 C 18.757 21 21 18.757 21 16 L 21 8 C 21 5.243 18.757 3 16 3 L 8 3 z M 8 5 L 16 5 C 17.654 5 19 6.346 19 8 L 19 16 C 19 17.654 17.654 19 16 19 L 8 19 C 6.346 19 5 17.654 5 16 L 5 8 C 5 6.346 6.346 5 8 5 z M 17 6 A 1 1 0 0 0 16 7 A 1 1 0 0 0 17 8 A 1 1 0 0 0 18 7 A 1 1 0 0 0 17 6 z M 12 7 C 9.243 7 7 9.243 7 12 C 7 14.757 9.243 17 12 17 C 14.757 17 17 14.757 17 12 C 17 9.243 14.757 7 12 7 z M 12 9 C 13.654 9 15 10.346 15 12 C 15 13.654 13.654 15 12 15 C 10.346 15 9 13.654 9 12 C 9 10.346 10.346 9 12 9 z"/>
  </symbol>
  
+  <symbol id="icon-notion" viewBox="0 0 24 24">
+    <path fill="currentColor" d="M6.104 5.91c.584.474.802.438 1.898.365l10.332-.62c.22 0 .037-.22-.036-.256l-1.716-1.24c-.329-.255-.767-.548-1.606-.475l-10.005.73c-.364.036-.437.219-.292.365zm.62 2.408v10.87c0 .585.292.803.95.767l11.354-.657c.657-.036.73-.438.73-.913V7.588c0-.474-.182-.73-.584-.693l-11.866.693c-.438.036-.584.255-.584.73m11.21.583c.072.328 0 .657-.33.694l-.547.109v8.025c-.475.256-.913.401-1.278.401c-.584 0-.73-.182-1.168-.729l-3.579-5.618v5.436l1.133.255s0 .656-.914.656l-2.519.146c-.073-.146 0-.51.256-.583l.657-.182v-7.187l-.913-.073c-.073-.329.11-.803.621-.84l2.702-.182l3.724 5.692V9.886l-.95-.109c-.072-.402.22-.693.585-.73zM4.131 3.429l10.406-.766c1.277-.11 1.606-.036 2.41.547l3.321 2.335c.548.401.731.51.731.948v12.805c0 .803-.292 1.277-1.314 1.35l-12.085.73c-.767.036-1.132-.073-1.534-.584L3.62 17.62c-.438-.584-.62-1.021-.62-1.533V4.705c0-.656.292-1.203 1.132-1.276"/>
+  </symbol>
+
  <symbol id="icon-shopify"  viewBox="0 0 32 32">
    <path fill="currentColor" d="m20.448 31.974l9.625-2.083s-3.474-23.484-3.5-23.641s-.156-.255-.281-.255c-.13 0-2.573-.182-2.573-.182s-1.703-1.698-1.922-1.88a.4.4 0 0 0-.161-.099l-1.219 28.141zm-4.833-16.901s-1.083-.563-2.365-.563c-1.932 0-2.005 1.203-2.005 1.521c0 1.641 4.318 2.286 4.318 6.172c0 3.057-1.922 5.01-4.542 5.01c-3.141 0-4.719-1.953-4.719-1.953l.859-2.781s1.661 1.422 3.042 1.422c.901 0 1.302-.724 1.302-1.245c0-2.156-3.542-2.255-3.542-5.807c-.047-2.984 2.094-5.891 6.438-5.891c1.677 0 2.5.479 2.5.479l-1.26 3.625zm-.719-13.969c.177 0 .359.052.536.182c-1.313.62-2.75 2.188-3.344 5.323a76 76 0 0 1-2.516.771c.688-2.38 2.359-6.26 5.323-6.26zm1.646 3.932v.182c-1.005.307-2.115.646-3.193.979c.62-2.37 1.776-3.526 2.781-3.958c.255.667.411 1.568.411 2.797zm.718-2.973c.922.094 1.521 1.151 1.901 2.339c-.464.151-.979.307-1.542.484v-.333c0-1.005-.13-1.828-.359-2.495zm3.99 1.718c-.031 0-.083.026-.104.026c-.026 0-.385.099-.953.281C19.63 2.442 18.625.927 16.849.927h-.156C16.183.281 15.558 0 15.021 0c-4.141 0-6.12 5.172-6.74 7.797c-1.594.484-2.75.844-2.88.896c-.901.286-.927.313-1.031 1.161c-.099.615-2.438 18.75-2.438 18.75L20.01 32z"/>
  </symbol>
+
  <symbol id="icon-slack" viewBox="0 0 24 24">
    <path fill="currentColor" d="M6.527 14.514A1.973 1.973 0 0 1 4.56 16.48a1.973 1.973 0 0 1-1.968-1.967c0-1.083.885-1.968 1.968-1.968h1.967zm.992 0c0-1.083.885-1.968 1.968-1.968s1.967.885 1.967 1.968v4.927a1.973 1.973 0 0 1-1.967 1.968a1.973 1.973 0 0 1-1.968-1.968zm1.968-7.987A1.973 1.973 0 0 1 7.519 4.56c0-1.083.885-1.967 1.968-1.967s1.967.884 1.967 1.967v1.968zm0 .992c1.083 0 1.967.884 1.967 1.967a1.973 1.973 0 0 1-1.967 1.968H4.56a1.973 1.973 0 0 1-1.968-1.968c0-1.083.885-1.967 1.968-1.967zm7.986 1.967c0-1.083.885-1.967 1.968-1.967s1.968.884 1.968 1.967a1.973 1.973 0 0 1-1.968 1.968h-1.968zm-.991 0a1.973 1.973 0 0 1-1.968 1.968a1.973 1.973 0 0 1-1.968-1.968V4.56c0-1.083.885-1.967 1.968-1.967s1.968.884 1.968 1.967zm-1.968 7.987c1.083 0 1.968.885 1.968 1.968a1.973 1.973 0 0 1-1.968 1.968a1.973 1.973 0 0 1-1.968-1.968v-1.968zm0-.992a1.973 1.973 0 0 1-1.968-1.967c0-1.083.885-1.968 1.968-1.968h4.927c1.083 0 1.968.885 1.968 1.968a1.973 1.973 0 0 1-1.968 1.967z"/>
  </symbol>
@@ -173,3 +173,6 @@
  display_name: Voice Channel
  enabled: false
  chatwoot_internal: true
+- name: notion_integration
+  display_name: Notion Integration
+  enabled: false
@@ -288,6 +288,25 @@
  type: secret
 ## ------ End of Configs added for Linear ------ ##

+## ------ Configs added for Notion ------ ##
+- name: NOTION_CLIENT_ID
+  display_title: 'Notion Client ID'
+  value:
+  locked: false
+  description: 'Notion client ID'
+- name: NOTION_CLIENT_SECRET
+  display_title: 'Notion Client Secret'
+  value:
+  locked: false
+  description: 'Notion client secret'
+  type: secret
+- name: NOTION_VERSION
+  display_title: 'Notion Version'
+  value: '2022-06-28'
+  locked: false
+  description: 'Notion version'
+## ------ End of Configs added for Notion ------ ##
+
 ## ------ Configs added for Slack ------ ##
 - name: SLACK_CLIENT_ID
  display_title: 'Slack Client ID'
@@ -63,6 +63,12 @@ linear:
  action: https://linear.app/oauth/authorize
  hook_type: account
  allow_multiple_hooks: false
+notion:
+  id: notion
+  logo: notion.png
+  i18n_key: notion
+  hook_type: account
+  allow_multiple_hooks: false
 slack:
  id: slack
  logo: slack.png
@@ -257,6 +257,10 @@ en:
      name: 'Linear'
      short_description: 'Create and link Linear issues directly from conversations.'
      description: 'Create issues in Linear directly from your conversation window. Alternatively, link existing Linear issues for a more streamlined and efficient issue tracking process.'
+    notion:
+      name: 'Notion'
+      short_description: 'Integrate databases, documents and pages directly with Captain.'
+      description: 'Connect your Notion workspace to enable Captain to access and generate intelligent responses using content from your databases, documents, and pages to provide more contextual customer support.'
    shopify:
      name: 'Shopify'
      short_description: 'Access order details and customer data from your Shopify store.'
@@ -228,6 +228,10 @@ Rails.application.routes.draw do
            resource :authorization, only: [:create]
          end

+          namespace :notion do
+            resource :authorization, only: [:create]
+          end
+
          resources :webhooks, only: [:index, :create, :update, :destroy]
          namespace :integrations do
            resources :apps, only: [:index, :show]
@@ -265,6 +269,11 @@ Rails.application.routes.draw do
                get :linked_issues
              end
            end
+            resource :notion, controller: 'notion', only: [] do
+              collection do
+                delete :destroy
+              end
+            end
          end
          resources :working_hours, only: [:update]

@@ -493,6 +502,7 @@ Rails.application.routes.draw do
  get 'microsoft/callback', to: 'microsoft/callbacks#show'
  get 'google/callback', to: 'google/callbacks#show'
  get 'instagram/callback', to: 'instagram/callbacks#show'
+  get 'notion/callback', to: 'notion/callbacks#show'
  # ----------------------------------------------------------------------
  # Routes for external service verifications
  get '.well-known/assetlinks.json' => 'android_app#assetlinks'
@@ -25,8 +25,8 @@ class Api::V1::Accounts::Captain::AssistantsController < Api::V1::Accounts::Base

  def playground
    response = Captain::Llm::AssistantChatService.new(assistant: @assistant).generate_response(
-      additional_message: params[:message_content],
-      message_history: message_history
+      params[:message_content],
+      message_history
    )

    render json: response
@@ -91,6 +91,12 @@ linear:
  enabled: true
  icon: 'icon-linear'
  config_key: 'linear'
+notion:
+  name: 'Notion'
+  description: 'Configuration for setting up Notion Integration'
+  enabled: true
+  icon: 'icon-notion'
+  config_key: 'notion'
 slack:
  name: 'Slack'
  description: 'Configuration for setting up Slack Integration'
@@ -26,7 +26,8 @@ class Captain::Conversation::ResponseBuilderJob < ApplicationJob

  def generate_and_process_response
    @response = Captain::Llm::AssistantChatService.new(assistant: @assistant).generate_response(
-      message_history: collect_previous_messages
+      @conversation.messages.incoming.last.content,
+      collect_previous_messages
    )

    return process_action('handoff') if handoff_requested?
@@ -42,11 +43,33 @@ class Captain::Conversation::ResponseBuilderJob < ApplicationJob
      .where(message_type: [:incoming, :outgoing])
      .where(private: false)
      .map do |message|
-      {
-        content: prepare_multimodal_message_content(message),
-        role: determine_role(message)
-      }
+        {
+          content: message_content(message),
+          role: determine_role(message)
+        }
+      end
+  end
+
+  def message_content(message)
+    return message.content if message.content.present?
+    return 'User has shared a message without content' unless message.attachments.any?
+
+    audio_transcriptions = extract_audio_transcriptions(message.attachments)
+    return audio_transcriptions if audio_transcriptions.present?
+
+    'User has shared an attachment'
+  end
+
+  def extract_audio_transcriptions(attachments)
+    audio_attachments = attachments.where(file_type: :audio)
+    return '' if audio_attachments.blank?
+
+    transcriptions = ''
+    audio_attachments.each do |attachment|
+      result = Messages::AudioTranscriptionService.new(attachment).perform
+      transcriptions += result[:transcriptions] if result[:success]
    end
+    transcriptions
  end

  def determine_role(message)
@@ -55,10 +78,6 @@ class Captain::Conversation::ResponseBuilderJob < ApplicationJob
    message.message_type == 'incoming' ? 'user' : 'system'
  end

-  def prepare_multimodal_message_content(message)
-    Captain::OpenAiMessageBuilderService.new(message: message).generate_content
-  end
-
  def handoff_requested?
    @response['response'] == 'conversation_handoff'
  end
@@ -12,16 +12,9 @@ class Captain::Llm::AssistantChatService < Llm::BaseOpenAiService
    register_tools
  end

-  # additional_message: A single message (String) from the user that should be appended to the chat.
-  #                    It can be an empty String or nil when you only want to supply historical messages.
-  # message_history:   An Array of already formatted messages that provide the previous context.
-  # role:              The role for the additional_message (defaults to `user`).
-  #
-  # NOTE: Parameters are provided as keyword arguments to improve clarity and avoid relying on
-  # positional ordering.
-  def generate_response(additional_message: nil, message_history: [], role: 'user')
-    @messages += message_history
-    @messages << { role: role, content: additional_message } if additional_message.present?
+  def generate_response(input, previous_messages = [], role = 'user')
+    @messages += previous_messages
+    @messages << { role: role, content: input } if input.present?
    request_chat_completion
  end

@@ -1,59 +0,0 @@
-class Captain::OpenAiMessageBuilderService
-  pattr_initialize [:message!]
-
-  def generate_content
-    parts = []
-    parts << text_part(@message.content) if @message.content.present?
-    parts.concat(attachment_parts(@message.attachments)) if @message.attachments.any?
-
-    return 'Message without content' if parts.blank?
-    return parts.first[:text] if parts.one? && parts.first[:type] == 'text'
-
-    parts
-  end
-
-  private
-
-  def text_part(text)
-    { type: 'text', text: text }
-  end
-
-  def image_part(image_url)
-    { type: 'image_url', image_url: { url: image_url } }
-  end
-
-  def attachment_parts(attachments)
-    image_attachments = attachments.where(file_type: :image)
-    image_content = image_parts(image_attachments)
-
-    transcription = extract_audio_transcriptions(attachments)
-    transcription_part = text_part(transcription) if transcription.present?
-
-    attachment_part = text_part('User has shared an attachment') if attachments.where.not(file_type: %i[image audio]).exists?
-
-    [image_content, transcription_part, attachment_part].flatten.compact
-  end
-
-  def image_parts(image_attachments)
-    image_attachments.each_with_object([]) do |attachment, parts|
-      url = get_attachment_url(attachment)
-      parts << image_part(url) if url.present?
-    end
-  end
-
-  def get_attachment_url(attachment)
-    return attachment.external_url if attachment.external_url.present?
-
-    attachment.file.attached? ? attachment.file_url : nil
-  end
-
-  def extract_audio_transcriptions(attachments)
-    audio_attachments = attachments.where(file_type: :audio)
-    return '' if audio_attachments.blank?
-
-    audio_attachments.map do |attachment|
-      result = Messages::AudioTranscriptionService.new(attachment).perform
-      result[:success] ? result[:transcriptions] : ''
-    end.join
-  end
-end
@@ -25,7 +25,6 @@ class Seeders::AccountSeeder
    seed_canned_responses
    seed_inboxes
    seed_contacts
-    seed_csat_responses
  end

  def set_up_account
@@ -117,17 +116,43 @@ class Seeders::AccountSeeder
        contact.update!(contact_data.slice('name', 'email'))
        Avatar::AvatarFromUrlJob.perform_later(contact, "https://xsgames.co/randomusers/avatar.php?g=#{contact_data['gender']}")
      end
+      contact_data['conversations'].each do |conversation_data|
+        inbox = @account.inboxes.find_by(channel_type: conversation_data['channel'])
+        contact_inbox = inbox.contact_inboxes.create_or_find_by!(contact: contact, source_id: (conversation_data['source_id'] || SecureRandom.hex))
+        create_conversation(contact_inbox: contact_inbox, conversation_data: conversation_data)
+      end
    end
+  end

-    # Create conversations after all contacts are created
-    Seeders::ConversationSeeder.new(account: @account, contact_data: @account_data['contacts']).perform!
+  def create_conversation(contact_inbox:, conversation_data:)
+    assignee = User.from_email(conversation_data['assignee']) if conversation_data['assignee'].present?
+    conversation = contact_inbox.conversations.create!(account: contact_inbox.inbox.account, contact: contact_inbox.contact,
+                                                       inbox: contact_inbox.inbox, assignee: assignee)
+    create_messages(conversation: conversation, messages: conversation_data['messages'])
+    conversation.update_labels(conversation_data[:labels]) if conversation_data[:labels].present?
+    conversation.update!(priority: conversation_data[:priority]) if conversation_data[:priority].present?
+  end
+
+  def create_messages(conversation:, messages:)
+    messages.each do |message_data|
+      sender = find_message_sender(conversation, message_data)
+      conversation.messages.create!(
+        message_data.slice('content', 'message_type').merge(
+          account: conversation.inbox.account, sender: sender, inbox: conversation.inbox
+        )
+      )
+    end
+  end
+
+  def find_message_sender(conversation, message_data)
+    if message_data['message_type'] == 'incoming'
+      conversation.contact
+    elsif message_data['sender'].present?
+      User.from_email(message_data['sender'])
+    end
  end

  def seed_inboxes
    Seeders::InboxSeeder.new(account: @account, company_data: @account_data[:company]).perform!
  end
-
-  def seed_csat_responses
-    Seeders::CsatSeeder.new(account: @account).perform!
-  end
 end
@@ -1,94 +0,0 @@
-## Class to generate sample conversations for a chatwoot test @Account.
-############################################################
-### Usage #####
-#
-#   # Seed an account with conversations
-#   Seeders::ConversationSeeder.new(account: Account.find(1), contact_data: []).perform!
-#
-#
-############################################################
-
-class Seeders::ConversationSeeder
-  def initialize(account:, contact_data:)
-    raise 'Conversation Seeding is not allowed in production.' unless ENV.fetch('ENABLE_ACCOUNT_SEEDING', !Rails.env.production?)
-
-    @account = account
-    @contact_data = contact_data
-  end
-
-  def perform!
-    seed_conversations
-  end
-
-  private
-
-  def seed_conversations
-    @contact_data.each do |contact_data|
-      contact = @account.contacts.find_by(email: contact_data['email'])
-      next unless contact
-
-      contact_data['conversations'].each do |conversation_data|
-        inbox = @account.inboxes.find_by(channel_type: conversation_data['channel'])
-        contact_inbox = inbox.contact_inboxes.create_or_find_by!(
-          contact: contact,
-          source_id: (conversation_data['source_id'] || SecureRandom.hex)
-        )
-        create_conversation(contact_inbox: contact_inbox, conversation_data: conversation_data)
-      end
-    end
-  end
-
-  def create_conversation(contact_inbox:, conversation_data:)
-    assignee = determine_assignee(conversation_data, contact_inbox.inbox)
-    conversation = build_conversation(contact_inbox, assignee)
-
-    create_messages(conversation: conversation, messages: conversation_data['messages'])
-    apply_conversation_attributes(conversation, conversation_data)
-    resolve_conversation_if_needed(conversation, assignee)
-  end
-
-  def determine_assignee(conversation_data, inbox)
-    assignee = User.from_email(conversation_data['assignee']) if conversation_data['assignee'].present?
-    assignee ||= @account.agents.sample if inbox.csat_survey_enabled
-    assignee
-  end
-
-  def build_conversation(contact_inbox, assignee)
-    contact_inbox.conversations.create!(
-      account: contact_inbox.inbox.account,
-      contact: contact_inbox.contact,
-      inbox: contact_inbox.inbox,
-      assignee: assignee
-    )
-  end
-
-  def apply_conversation_attributes(conversation, conversation_data)
-    conversation.update_labels(conversation_data[:labels]) if conversation_data[:labels].present?
-    conversation.update!(priority: conversation_data[:priority]) if conversation_data[:priority].present?
-  end
-
-  def resolve_conversation_if_needed(conversation, assignee)
-    return unless assignee.present? && rand > 0.4
-
-    conversation.update!(status: :resolved)
-  end
-
-  def create_messages(conversation:, messages:)
-    messages.each do |message_data|
-      sender = find_message_sender(conversation, message_data)
-      conversation.messages.create!(
-        message_data.slice('content', 'message_type').merge(
-          account: conversation.inbox.account, sender: sender, inbox: conversation.inbox
-        )
-      )
-    end
-  end
-
-  def find_message_sender(conversation, message_data)
-    if message_data['message_type'] == 'incoming'
-      conversation.contact
-    elsif message_data['sender'].present?
-      User.from_email(message_data['sender'])
-    end
-  end
-end
@@ -1,88 +0,0 @@
-## Class to generate sample CSAT survey responses for a chatwoot test @Account.
-############################################################
-### Usage #####
-#
-#   # Seed an account with CSAT responses
-#   Seeders::CsatSeeder.new(account: Account.find(1)).perform!
-#
-#
-############################################################
-
-class Seeders::CsatSeeder
-  def initialize(account:)
-    raise 'CSAT Seeding is not allowed in production.' unless ENV.fetch('ENABLE_ACCOUNT_SEEDING', !Rails.env.production?)
-
-    @account = account
-  end
-
-  def perform!
-    seed_csat_responses
-  end
-
-  private
-
-  def seed_csat_responses
-    resolved_conversations = @account.conversations.where(status: :resolved)
-    csat_enabled_inboxes = @account.inboxes.where(csat_survey_enabled: true)
-
-    return if resolved_conversations.empty? || csat_enabled_inboxes.empty?
-
-    # Create CSAT responses for resolved conversations in CSAT-enabled inboxes
-    resolved_conversations.joins(:inbox).where(inbox: csat_enabled_inboxes).find_each do |conversation|
-      # Only create CSAT for about 70% of resolved conversations to simulate real-world scenarios
-      next if rand > 0.7
-
-      # Get the last outgoing message to attach CSAT to
-      last_outgoing_message = conversation.messages.where(message_type: :outgoing).last
-      next unless last_outgoing_message
-
-      # Create CSAT survey response with varied ratings and feedback
-      create_csat_response(conversation, last_outgoing_message)
-    end
-  end
-
-  def create_csat_response(conversation, message)
-    # Generate realistic rating distribution (more positive ratings)
-    rating = case rand
-             when 0.0..0.05 then 1  # 5%
-             when 0.05..0.15 then 2 # 10%
-             when 0.15..0.35 then 3 # 20%
-             when 0.35..0.65 then 4 # 30%
-             else 5                 # 35%
-             end
-
-    feedback_messages = [
-      'Great service, very helpful!',
-      'Quick response and resolved my issue',
-      'Professional and courteous support',
-      'Could be faster but overall good',
-      'Satisfied with the resolution',
-      'Excellent customer service',
-      'Very knowledgeable agent',
-      'Resolved quickly, thank you!',
-      'Good experience overall',
-      'Agent was very patient and helpful',
-      'Really appreciate the help',
-      'Fast and efficient service',
-      'Agent went above and beyond',
-      'Clear explanations provided',
-      'Issue resolved on first contact',
-      '',  # Some responses have no feedback
-      '',
-      ''
-    ]
-
-    CsatSurveyResponse.create!(
-      account: @account,
-      conversation: conversation,
-      contact: conversation.contact,
-      message: message,
-      assigned_agent: conversation.assignee,
-      rating: rating,
-      feedback_message: feedback_messages.sample,
-      created_at: message.created_at + rand(5..30).minutes
-    )
-  rescue StandardError => e
-    Rails.logger.debug { "Failed to create CSAT response: #{e.message}" }
-  end
-end
@@ -30,31 +30,13 @@ class Seeders::InboxSeeder

  def seed_website_inbox
    channel = Channel::WebWidget.create!(account: @account, website_url: "https://#{@company_data['domain']}")
-    Inbox.create!(
-      channel: channel,
-      account: @account,
-      name: "#{@company_data['name']} Website",
-      csat_survey_enabled: true,
-      csat_config: {
-        'display_type' => 'emoji',
-        'message' => 'How would you rate your experience?'
-      }
-    )
+    Inbox.create!(channel: channel, account: @account, name: "#{@company_data['name']} Website")
  end

  def seed_facebook_inbox
    channel = Channel::FacebookPage.create!(account: @account, user_access_token: SecureRandom.hex, page_access_token: SecureRandom.hex,
                                            page_id: SecureRandom.hex)
-    Inbox.create!(
-      channel: channel,
-      account: @account,
-      name: "#{@company_data['name']} Facebook",
-      csat_survey_enabled: true,
-      csat_config: {
-        'display_type' => 'star',
-        'message' => 'Please rate your support experience'
-      }
-    )
+    Inbox.create!(channel: channel, account: @account, name: "#{@company_data['name']} Facebook")
  end

  def seed_twitter_inbox
@@ -89,16 +71,7 @@ class Seeders::InboxSeeder
  def seed_email_inbox
    channel = Channel::Email.create!(account: @account, email: "test#{SecureRandom.hex}@#{@company_data['domain']}",
                                     forward_to_email: "test_fwd#{SecureRandom.hex}@#{@company_data['domain']}")
-    Inbox.create!(
-      channel: channel,
-      account: @account,
-      name: "#{@company_data['name']} Email",
-      csat_survey_enabled: true,
-      csat_config: {
-        'display_type' => 'emoji',
-        'message' => 'How was your support experience today?'
-      }
-    )
+    Inbox.create!(channel: channel, account: @account, name: "#{@company_data['name']} Email")
  end

  def seed_api_inbox
@@ -477,55 +477,4 @@ contacts:
            - message_type: outgoing
              sender: michael_scott@paperlayer.test
              content: How may i help you ?
-    - name: "Robert Maxwell"
-      email: "rmaxwell@example.test"
-      gender: 'male'
-      conversations:
-        - channel: Channel::WebWidget
-          assignee: karn@paperlayer.test
-          messages:
-            - message_type: incoming
-              content: "Hi, I need help with my account settings."
-            - message_type: outgoing
-              sender: karn@paperlayer.test
-              content: "I'd be happy to help you with your account settings. What specifically would you like to change?"
-            - message_type: incoming
-              content: "I want to update my billing information."
-            - message_type: outgoing
-              sender: karn@paperlayer.test
-              content: "Perfect! I've sent you a secure link to update your billing information. Please check your email."
-    - name: "Sarah Johnson"
-      email: "sjohnson@demo.test"
-      gender: 'female'
-      conversations:
-        - channel: Channel::FacebookPage
-          assignee: danny@paperlayer.test
-          messages:
-            - message_type: incoming
-              content: "Hello, I'm having trouble with the mobile app."
-            - message_type: outgoing
-              sender: danny@paperlayer.test
-              content: "Sorry to hear that! Can you tell me what specific issue you're experiencing?"
-            - message_type: incoming
-              content: "The app keeps crashing when I try to upload a document."
-            - message_type: outgoing
-              sender: danny@paperlayer.test
-              content: "I understand how frustrating that must be. Let me help you troubleshoot this issue right away."
-    - name: "David Chen"
-      email: "dchen@sample.test"
-      gender: 'male'
-      conversations:
-        - channel: Channel::Email
-          source_id: "dchen@sample.test"
-          assignee: ben@paperlayer.test
-          messages:
-            - message_type: incoming
-              content: "I need assistance with integrating your API."
-            - message_type: outgoing
-              sender: ben@paperlayer.test
-              content: "I'll be happy to help with the API integration. What programming language are you using?"
-            - message_type: incoming
-              content: "We're using Python for our backend."
-            - message_type: outgoing
-              sender: ben@paperlayer.test
-              content: "Great! I'll send you our Python SDK documentation and some sample code to get you started."
+              sender: michael_scott@paperlayer.test
@@ -0,0 +1,53 @@
+require 'rails_helper'
+
+RSpec.describe 'Notion Authorization API', type: :request do
+  let(:account) { create(:account) }
+
+  describe 'POST /api/v1/accounts/{account.id}/notion/authorization' do
+    context 'when it is an unauthenticated user' do
+      it 'returns unauthorized' do
+        post "/api/v1/accounts/#{account.id}/notion/authorization"
+
+        expect(response).to have_http_status(:unauthorized)
+      end
+    end
+
+    context 'when it is an authenticated user' do
+      let(:agent) { create(:user, account: account, role: :agent) }
+      let(:administrator) { create(:user, account: account, role: :administrator) }
+
+      it 'returns unauthorized for agent' do
+        post "/api/v1/accounts/#{account.id}/notion/authorization",
+             headers: agent.create_new_auth_token,
+             params: { email: administrator.email },
+             as: :json
+
+        expect(response).to have_http_status(:unauthorized)
+      end
+
+      it 'creates a new authorization and returns the redirect url' do
+        post "/api/v1/accounts/#{account.id}/notion/authorization",
+             headers: administrator.create_new_auth_token,
+             params: { email: administrator.email },
+             as: :json
+
+        expect(response).to have_http_status(:success)
+
+        # Validate URL components
+        url = response.parsed_body['url']
+        uri = URI.parse(url)
+        params = CGI.parse(uri.query)
+
+        expect(url).to start_with('https://api.notion.com/v1/oauth/authorize')
+        expect(params['response_type']).to eq(['code'])
+        expect(params['owner']).to eq(['user'])
+        expect(params['redirect_uri']).to eq(["#{ENV.fetch('FRONTEND_URL', 'http://localhost:3000')}/notion/callback"])
+
+        # Validate state parameter exists and can be decoded back to the account
+        expect(params['state']).to be_present
+        decoded_account = GlobalID::Locator.locate_signed(params['state'].first, for: 'default')
+        expect(decoded_account).to eq(account)
+      end
+    end
+  end
+end
@@ -0,0 +1,56 @@
+require 'rails_helper'
+
+RSpec.describe NotionConcern, type: :concern do
+  let(:controller_class) do
+    Class.new do
+      include NotionConcern
+    end
+  end
+
+  let(:controller) { controller_class.new }
+
+  describe '#notion_client' do
+    let(:client_id) { 'test_notion_client_id' }
+    let(:client_secret) { 'test_notion_client_secret' }
+
+    before do
+      allow(GlobalConfigService).to receive(:load).with('NOTION_CLIENT_ID', nil).and_return(client_id)
+      allow(GlobalConfigService).to receive(:load).with('NOTION_CLIENT_SECRET', nil).and_return(client_secret)
+    end
+
+    it 'creates OAuth2 client with correct configuration' do
+      expect(OAuth2::Client).to receive(:new).with(
+        client_id,
+        client_secret,
+        {
+          site: 'https://api.notion.com',
+          authorize_url: 'https://api.notion.com/v1/oauth/authorize',
+          token_url: 'https://api.notion.com/v1/oauth/token',
+          auth_scheme: :basic_auth
+        }
+      )
+
+      controller.notion_client
+    end
+
+    it 'loads client credentials from GlobalConfigService' do
+      expect(GlobalConfigService).to receive(:load).with('NOTION_CLIENT_ID', nil)
+      expect(GlobalConfigService).to receive(:load).with('NOTION_CLIENT_SECRET', nil)
+
+      controller.notion_client
+    end
+
+    it 'returns OAuth2::Client instance' do
+      client = controller.notion_client
+      expect(client).to be_an_instance_of(OAuth2::Client)
+    end
+
+    it 'configures client with Notion-specific endpoints' do
+      client = controller.notion_client
+      expect(client.site).to eq('https://api.notion.com')
+      expect(client.options[:authorize_url]).to eq('https://api.notion.com/v1/oauth/authorize')
+      expect(client.options[:token_url]).to eq('https://api.notion.com/v1/oauth/token')
+      expect(client.options[:auth_scheme]).to eq(:basic_auth)
+    end
+  end
+end
@@ -0,0 +1,112 @@
+require 'rails_helper'
+
+RSpec.describe Notion::CallbacksController, type: :request do
+  let(:account) { create(:account) }
+  let(:state) { account.to_sgid.to_s }
+  let(:oauth_code) { 'test_oauth_code' }
+  let(:notion_redirect_uri) { "#{ENV.fetch('FRONTEND_URL', 'http://localhost:3000')}/app/accounts/#{account.id}/settings/integrations/notion" }
+
+  let(:notion_response_body) do
+    {
+      'access_token' => 'notion_access_token_123',
+      'token_type' => 'bearer',
+      'workspace_name' => 'Test Workspace',
+      'workspace_id' => 'workspace_123',
+      'workspace_icon' => 'https://notion.so/icon.png',
+      'bot_id' => 'bot_123',
+      'owner' => {
+        'type' => 'user',
+        'user' => {
+          'id' => 'user_123',
+          'name' => 'Test User'
+        }
+      }
+    }
+  end
+
+  describe 'GET /notion/callback' do
+    before do
+      account.enable_features('notion_integration')
+      stub_const('ENV', ENV.to_hash.merge(
+                          'FRONTEND_URL' => 'http://localhost:3000',
+                          'NOTION_CLIENT_ID' => 'test_client_id',
+                          'NOTION_CLIENT_SECRET' => 'test_client_secret'
+                        ))
+
+      controller = described_class.new
+      allow(controller).to receive(:account).and_return(account)
+      allow(controller).to receive(:notion_redirect_uri).and_return(notion_redirect_uri)
+      allow(described_class).to receive(:new).and_return(controller)
+    end
+
+    context 'when OAuth callback is successful' do
+      before do
+        stub_request(:post, 'https://api.notion.com/v1/oauth/token')
+          .to_return(
+            status: 200,
+            body: notion_response_body.to_json,
+            headers: { 'Content-Type' => 'application/json' }
+          )
+      end
+
+      it 'creates a new integration hook' do
+        expect do
+          get '/notion/callback', params: { code: oauth_code, state: state }
+        end.to change(Integrations::Hook, :count).by(1)
+
+        hook = Integrations::Hook.last
+        expect(hook.access_token).to eq('notion_access_token_123')
+        expect(hook.app_id).to eq('notion')
+        expect(hook.status).to eq('enabled')
+      end
+
+      it 'sets correct hook attributes' do
+        get '/notion/callback', params: { code: oauth_code, state: state }
+
+        hook = Integrations::Hook.last
+        expect(hook.account).to eq(account)
+        expect(hook.app_id).to eq('notion')
+        expect(hook.access_token).to eq('notion_access_token_123')
+        expect(hook.status).to eq('enabled')
+      end
+
+      it 'stores notion workspace data in settings' do
+        get '/notion/callback', params: { code: oauth_code, state: state }
+
+        hook = Integrations::Hook.last
+        expect(hook.settings['token_type']).to eq('bearer')
+        expect(hook.settings['workspace_name']).to eq('Test Workspace')
+        expect(hook.settings['workspace_id']).to eq('workspace_123')
+        expect(hook.settings['workspace_icon']).to eq('https://notion.so/icon.png')
+        expect(hook.settings['bot_id']).to eq('bot_123')
+        expect(hook.settings['owner']).to eq(notion_response_body['owner'])
+      end
+
+      it 'handles successful callback and creates hook' do
+        get '/notion/callback', params: { code: oauth_code, state: state }
+
+        # Due to controller mocking limitations in test,
+        # the redirect URL construction fails but hook creation succeeds
+        expect(Integrations::Hook.last.app_id).to eq('notion')
+        expect(response).to be_redirect
+      end
+    end
+
+    context 'when OAuth token request fails' do
+      before do
+        stub_request(:post, 'https://api.notion.com/v1/oauth/token')
+          .to_return(
+            status: 400,
+            body: { error: 'invalid_grant' }.to_json,
+            headers: { 'Content-Type' => 'application/json' }
+          )
+      end
+
+      it 'redirects to home page on error' do
+        get '/notion/callback', params: { code: oauth_code, state: state }
+
+        expect(response).to redirect_to('/')
+      end
+    end
+  end
+end
@@ -211,8 +211,8 @@ RSpec.describe 'Api::V1::Accounts::Captain::Assistants', type: :request do

        expect(response).to have_http_status(:success)
        expect(chat_service).to have_received(:generate_response).with(
-          additional_message: valid_params[:message_content],
-          message_history: valid_params[:message_history]
+          valid_params[:message_content],
+          valid_params[:message_history]
        )
        expect(json_response[:content]).to eq('Assistant response')
      end
@@ -232,8 +232,8 @@ RSpec.describe 'Api::V1::Accounts::Captain::Assistants', type: :request do

        expect(response).to have_http_status(:success)
        expect(chat_service).to have_received(:generate_response).with(
-          additional_message: params_without_history[:message_content],
-          message_history: []
+          params_without_history[:message_content],
+          []
        )
      end
    end
@@ -30,30 +30,5 @@ RSpec.describe Captain::Conversation::ResponseBuilderJob, type: :job do
      account.reload
      expect(account.usage_limits[:captain][:responses][:consumed]).to eq(1)
    end
-
-    context 'when message contains an image' do
-      let(:message_with_image) { create(:message, conversation: conversation, message_type: :incoming, content: 'Can you help with this error?') }
-      let(:image_attachment) { message_with_image.attachments.create!(account: account, file_type: :image, external_url: 'https://example.com/error.jpg') }
-
-      before do
-        image_attachment
-      end
-
-      it 'includes image URL directly in the message content for OpenAI vision analysis' do
-        # Expect the generate_response to receive multimodal content with image URL
-        expect(mock_llm_chat_service).to receive(:generate_response) do |**kwargs|
-          history = kwargs[:message_history]
-          last_entry = history.last
-          expect(last_entry[:content]).to be_an(Array)
-          expect(last_entry[:content].any? { |part| part[:type] == 'text' && part[:text] == 'Can you help with this error?' }).to be true
-          expect(last_entry[:content].any? do |part|
-            part[:type] == 'image_url' && part[:image_url][:url] == 'https://example.com/error.jpg'
-          end).to be true
-          { 'response' => 'I can see the error in your image. It appears to be a database connection issue.' }
-        end
-
-        described_class.perform_now(conversation, assistant)
-      end
-    end
  end
 end
@@ -1,309 +0,0 @@
-require 'rails_helper'
-
-RSpec.describe Captain::OpenAiMessageBuilderService do
-  subject(:service) { described_class.new(message: message) }
-
-  let(:message) { create(:message, content: 'Hello world') }
-
-  describe '#generate_content' do
-    context 'when message has only text content' do
-      it 'returns the text content directly' do
-        expect(service.generate_content).to eq('Hello world')
-      end
-    end
-
-    context 'when message has no content and no attachments' do
-      let(:message) { create(:message, content: nil) }
-
-      it 'returns default message' do
-        expect(service.generate_content).to eq('Message without content')
-      end
-    end
-
-    context 'when message has text content and attachments' do
-      before do
-        attachment = message.attachments.build(account_id: message.account_id, file_type: :image, external_url: 'https://example.com/image.jpg')
-        attachment.save!
-      end
-
-      it 'returns an array of content parts' do
-        result = service.generate_content
-        expect(result).to be_an(Array)
-        expect(result).to include({ type: 'text', text: 'Hello world' })
-        expect(result).to include({ type: 'image_url', image_url: { url: 'https://example.com/image.jpg' } })
-      end
-    end
-
-    context 'when message has only non-text attachments' do
-      let(:message) { create(:message, content: nil) }
-
-      before do
-        attachment = message.attachments.build(account_id: message.account_id, file_type: :image, external_url: 'https://example.com/image.jpg')
-        attachment.save!
-      end
-
-      it 'returns an array of content parts without text' do
-        result = service.generate_content
-        expect(result).to be_an(Array)
-        expect(result).to include({ type: 'image_url', image_url: { url: 'https://example.com/image.jpg' } })
-        expect(result).not_to include(hash_including(type: 'text', text: 'Hello world'))
-      end
-    end
-  end
-
-  describe '#attachment_parts' do
-    let(:message) { create(:message, content: nil) }
-    let(:attachments) { message.attachments }
-
-    context 'with image attachments' do
-      before do
-        attachment = message.attachments.build(account_id: message.account_id, file_type: :image, external_url: 'https://example.com/image.jpg')
-        attachment.save!
-      end
-
-      it 'includes image parts' do
-        result = service.send(:attachment_parts, attachments)
-        expect(result).to include({ type: 'image_url', image_url: { url: 'https://example.com/image.jpg' } })
-      end
-    end
-
-    context 'with audio attachments' do
-      let(:audio_attachment) do
-        attachment = message.attachments.build(account_id: message.account_id, file_type: :audio)
-        attachment.save!
-        attachment
-      end
-
-      before do
-        allow(Messages::AudioTranscriptionService).to receive(:new).with(audio_attachment).and_return(
-          instance_double(Messages::AudioTranscriptionService, perform: { success: true, transcriptions: 'Audio transcription text' })
-        )
-      end
-
-      it 'includes transcription text part' do
-        audio_attachment # trigger creation
-        result = service.send(:attachment_parts, attachments)
-        expect(result).to include({ type: 'text', text: 'Audio transcription text' })
-      end
-    end
-
-    context 'with other file types' do
-      before do
-        attachment = message.attachments.build(account_id: message.account_id, file_type: :file)
-        attachment.save!
-      end
-
-      it 'includes generic attachment message' do
-        result = service.send(:attachment_parts, attachments)
-        expect(result).to include({ type: 'text', text: 'User has shared an attachment' })
-      end
-    end
-
-    context 'with mixed attachment types' do
-      let(:image_attachment) do
-        attachment = message.attachments.build(account_id: message.account_id, file_type: :image, external_url: 'https://example.com/image.jpg')
-        attachment.save!
-        attachment
-      end
-
-      let(:audio_attachment) do
-        attachment = message.attachments.build(account_id: message.account_id, file_type: :audio)
-        attachment.save!
-        attachment
-      end
-
-      let(:document_attachment) do
-        attachment = message.attachments.build(account_id: message.account_id, file_type: :file)
-        attachment.save!
-        attachment
-      end
-
-      before do
-        allow(Messages::AudioTranscriptionService).to receive(:new).with(audio_attachment).and_return(
-          instance_double(Messages::AudioTranscriptionService, perform: { success: true, transcriptions: 'Audio text' })
-        )
-      end
-
-      it 'includes all relevant parts' do
-        image_attachment    # trigger creation
-        audio_attachment    # trigger creation
-        document_attachment # trigger creation
-
-        result = service.send(:attachment_parts, attachments)
-        expect(result).to include({ type: 'image_url', image_url: { url: 'https://example.com/image.jpg' } })
-        expect(result).to include({ type: 'text', text: 'Audio text' })
-        expect(result).to include({ type: 'text', text: 'User has shared an attachment' })
-      end
-    end
-  end
-
-  describe '#image_parts' do
-    let(:message) { create(:message, content: nil) }
-
-    context 'with valid image attachments' do
-      let(:image1) do
-        attachment = message.attachments.build(account_id: message.account_id, file_type: :image, external_url: 'https://example.com/image1.jpg')
-        attachment.save!
-        attachment
-      end
-
-      let(:image2) do
-        attachment = message.attachments.build(account_id: message.account_id, file_type: :image, external_url: 'https://example.com/image2.jpg')
-        attachment.save!
-        attachment
-      end
-
-      it 'returns image parts for all valid images' do
-        image1 # trigger creation
-        image2 # trigger creation
-
-        image_attachments = message.attachments.where(file_type: :image)
-        result = service.send(:image_parts, image_attachments)
-
-        expect(result).to include({ type: 'image_url', image_url: { url: 'https://example.com/image1.jpg' } })
-        expect(result).to include({ type: 'image_url', image_url: { url: 'https://example.com/image2.jpg' } })
-      end
-    end
-
-    context 'with image attachments without URLs' do
-      let(:image_attachment) do
-        attachment = message.attachments.build(account_id: message.account_id, file_type: :image, external_url: nil)
-        attachment.save!
-        attachment
-      end
-
-      before do
-        allow(image_attachment).to receive(:file).and_return(instance_double(ActiveStorage::Attached::One, attached?: false))
-      end
-
-      it 'skips images without valid URLs' do
-        image_attachment # trigger creation
-
-        image_attachments = message.attachments.where(file_type: :image)
-        result = service.send(:image_parts, image_attachments)
-
-        expect(result).to be_empty
-      end
-    end
-  end
-
-  describe '#get_attachment_url' do
-    let(:attachment) do
-      attachment = message.attachments.build(account_id: message.account_id, file_type: :image)
-      attachment.save!
-      attachment
-    end
-
-    context 'when attachment has external_url' do
-      before { attachment.update(external_url: 'https://example.com/image.jpg') }
-
-      it 'returns external_url' do
-        expect(service.send(:get_attachment_url, attachment)).to eq('https://example.com/image.jpg')
-      end
-    end
-
-    context 'when attachment has attached file' do
-      before do
-        attachment.update(external_url: nil)
-        allow(attachment).to receive(:file).and_return(instance_double(ActiveStorage::Attached::One, attached?: true))
-        allow(attachment).to receive(:file_url).and_return('https://local.com/file.jpg')
-      end
-
-      it 'returns file_url' do
-        expect(service.send(:get_attachment_url, attachment)).to eq('https://local.com/file.jpg')
-      end
-    end
-
-    context 'when attachment has no URL or file' do
-      before do
-        attachment.update(external_url: nil)
-        allow(attachment).to receive(:file).and_return(instance_double(ActiveStorage::Attached::One, attached?: false))
-      end
-
-      it 'returns nil' do
-        expect(service.send(:get_attachment_url, attachment)).to be_nil
-      end
-    end
-  end
-
-  describe '#extract_audio_transcriptions' do
-    let(:message) { create(:message, content: nil) }
-
-    context 'with no audio attachments' do
-      it 'returns empty string' do
-        result = service.send(:extract_audio_transcriptions, message.attachments)
-        expect(result).to eq('')
-      end
-    end
-
-    context 'with successful audio transcriptions' do
-      let(:audio1) do
-        attachment = message.attachments.build(account_id: message.account_id, file_type: :audio)
-        attachment.save!
-        attachment
-      end
-
-      let(:audio2) do
-        attachment = message.attachments.build(account_id: message.account_id, file_type: :audio)
-        attachment.save!
-        attachment
-      end
-
-      before do
-        allow(Messages::AudioTranscriptionService).to receive(:new).with(audio1).and_return(
-          instance_double(Messages::AudioTranscriptionService, perform: { success: true, transcriptions: 'First audio text. ' })
-        )
-        allow(Messages::AudioTranscriptionService).to receive(:new).with(audio2).and_return(
-          instance_double(Messages::AudioTranscriptionService, perform: { success: true, transcriptions: 'Second audio text.' })
-        )
-      end
-
-      it 'concatenates all successful transcriptions' do
-        audio1 # trigger creation
-        audio2 # trigger creation
-
-        attachments = message.attachments
-        result = service.send(:extract_audio_transcriptions, attachments)
-        expect(result).to eq('First audio text. Second audio text.')
-      end
-    end
-
-    context 'with failed audio transcriptions' do
-      let(:audio_attachment) do
-        attachment = message.attachments.build(account_id: message.account_id, file_type: :audio)
-        attachment.save!
-        attachment
-      end
-
-      before do
-        allow(Messages::AudioTranscriptionService).to receive(:new).with(audio_attachment).and_return(
-          instance_double(Messages::AudioTranscriptionService, perform: { success: false, transcriptions: nil })
-        )
-      end
-
-      it 'returns empty string for failed transcriptions' do
-        audio_attachment # trigger creation
-
-        attachments = message.attachments
-        result = service.send(:extract_audio_transcriptions, attachments)
-        expect(result).to eq('')
-      end
-    end
-  end
-
-  describe 'private helper methods' do
-    describe '#text_part' do
-      it 'returns correct text part format' do
-        result = service.send(:text_part, 'Hello world')
-        expect(result).to eq({ type: 'text', text: 'Hello world' })
-      end
-    end
-
-    describe '#image_part' do
-      it 'returns correct image part format' do
-        result = service.send(:image_part, 'https://example.com/image.jpg')
-        expect(result).to eq({ type: 'image_url', image_url: { url: 'https://example.com/image.jpg' } })
-      end
-    end
-  end
-end
@@ -66,6 +66,34 @@ describe ReportingEventListener do
  end

  describe '#reply_created' do
+    let(:contact) { create(:contact, account: account) }
+
+    def create_customer_message(conversation, created_at: Time.current)
+      create(:message,
+             message_type: 'incoming',
+             account: account,
+             inbox: inbox,
+             conversation: conversation,
+             sender: contact,
+             created_at: created_at)
+    end
+
+    def create_agent_message(conversation, created_at: Time.current, sender: user)
+      create(:message,
+             message_type: 'outgoing',
+             account: account,
+             inbox: inbox,
+             conversation: conversation,
+             sender: sender,
+             created_at: created_at)
+    end
+
+    def create_reply_event(agent_message, waiting_since, event_time = nil)
+      Events::Base.new('reply.created', event_time || agent_message.created_at,
+                       waiting_since: waiting_since,
+                       message: agent_message)
+    end
+
    it 'creates reply created event' do
      event = Events::Base.new('reply.created', Time.zone.now, waiting_since: 2.hours.ago, message: message)
      listener.reply_created(event)
@@ -74,6 +102,88 @@ describe ReportingEventListener do
      expect(events.length).to be 1
      expect(events.first.value).to be_within(1).of(7200)
    end
+
+    context 'when conversation is reopened' do
+      let(:resolved_conversation) do
+        create(:conversation, account: account, inbox: inbox, assignee: user,
+                              status: 'resolved', contact: contact)
+      end
+
+      context 'when customer sends message after resolution' do
+        it 'calculates reply time from the reopening message' do
+          customer_message_time = 3.hours.ago
+          create_customer_message(resolved_conversation, created_at: customer_message_time)
+
+          resolved_conversation.reload
+          expect(resolved_conversation.status).to eq('open')
+
+          agent_reply_time = 1.hour.ago
+          agent_message = create_agent_message(resolved_conversation, created_at: agent_reply_time)
+
+          event = create_reply_event(agent_message, customer_message_time)
+          listener.reply_created(event)
+
+          events = account.reporting_events.where(name: 'reply_time', conversation_id: resolved_conversation.id)
+          expect(events.length).to be 1
+          expect(events.first.value).to be_within(60).of(7200)
+        end
+      end
+
+      context 'when conversation has multiple reopenings' do
+        it 'tracks reply time correctly for each reopening' do
+          create_customer_message(resolved_conversation, created_at: 5.hours.ago)
+          first_agent_reply = create_agent_message(resolved_conversation, created_at: 4.hours.ago)
+
+          event = create_reply_event(first_agent_reply, 5.hours.ago)
+          listener.reply_created(event)
+
+          resolved_conversation.update!(status: 'resolved')
+
+          create_customer_message(resolved_conversation, created_at: 2.hours.ago)
+          second_agent_reply = create_agent_message(resolved_conversation, created_at: 1.5.hours.ago)
+
+          event = create_reply_event(second_agent_reply, 2.hours.ago)
+          listener.reply_created(event)
+
+          events = account.reporting_events.where(name: 'reply_time', conversation_id: resolved_conversation.id)
+                          .order(created_at: :asc)
+          expect(events.length).to be 2
+          expect(events.first.value).to be_within(60).of(3600)
+          expect(events.second.value).to be_within(60).of(1800)
+        end
+      end
+
+      context 'when conversation is manually reopened' do
+        it 'sets waiting_since when first customer message arrives after manual reopening' do
+          resolved_conversation.update!(status: 'open')
+
+          customer_message_time = 1.hour.ago
+          create_customer_message(resolved_conversation, created_at: customer_message_time)
+
+          agent_reply_time = 15.minutes.ago
+          agent_message = create_agent_message(resolved_conversation, created_at: agent_reply_time)
+
+          event = create_reply_event(agent_message, customer_message_time)
+          listener.reply_created(event)
+
+          events = account.reporting_events.where(name: 'reply_time', conversation_id: resolved_conversation.id)
+          expect(events.length).to be 1
+          expect(events.first.value).to be_within(60).of(2700)
+        end
+      end
+
+      context 'when waiting_since is nil' do
+        it 'does not creates reply time events' do
+          agent_message = create_agent_message(resolved_conversation)
+
+          event = create_reply_event(agent_message, nil)
+          listener.reply_created(event)
+
+          events = account.reporting_events.where(name: 'reply_time', conversation_id: resolved_conversation.id)
+          expect(events.length).to be 0
+        end
+      end
+    end
  end

  describe '#first_reply_created' do
@@ -836,4 +836,117 @@ RSpec.describe Conversation do
      expect(message_window_service).to have_received(:can_reply?)
    end
  end
+
+  describe 'reply time calculation flows' do
+    include ActiveJob::TestHelper
+
+    let(:account) { create(:account) }
+    let(:inbox) { create(:inbox, account: account) }
+    let(:contact) { create(:contact, account: account) }
+    let(:agent) { create(:user, account: account, role: :agent) }
+    let(:conversation) { create(:conversation, account: account, inbox: inbox, contact: contact, assignee: agent, waiting_since: nil) }
+    let(:conversation_start_time) { 5.hours.ago }
+
+    before do
+      create(:inbox_member, user: agent, inbox: inbox)
+      # rubocop:disable Rails/SkipsModelValidations
+      conversation.update_column(:waiting_since, nil)
+      conversation.update_column(:created_at, conversation_start_time)
+      # rubocop:enable Rails/SkipsModelValidations
+      conversation.messages.destroy_all
+      conversation.reporting_events.destroy_all
+      conversation.reload
+    end
+
+    def create_customer_message(conversation, created_at: Time.current)
+      message = nil
+      perform_enqueued_jobs do
+        message = create(:message,
+                         message_type: 'incoming',
+                         account: conversation.account,
+                         inbox: conversation.inbox,
+                         conversation: conversation,
+                         sender: conversation.contact,
+                         created_at: created_at)
+      end
+      message
+    end
+
+    def create_agent_message(conversation, created_at: Time.current)
+      message = nil
+      perform_enqueued_jobs do
+        message = create(:message,
+                         message_type: 'outgoing',
+                         account: conversation.account,
+                         inbox: conversation.inbox,
+                         conversation: conversation,
+                         sender: conversation.assignee,
+                         created_at: created_at)
+      end
+      message
+    end
+
+    it 'correctly tracks waiting_since and creates first response time events' do
+      create_customer_message(conversation, created_at: conversation_start_time)
+      conversation.reload
+      expect(conversation.waiting_since).to be_within(1.second).of(conversation_start_time)
+
+      # Agent replies - this should create first response event
+      agent_reply1_time = 4.hours.ago
+      create_agent_message(conversation, created_at: agent_reply1_time)
+
+      first_response_events = account.reporting_events.where(name: 'first_response', conversation_id: conversation.id)
+      expect(first_response_events.count).to eq(1)
+      expect(first_response_events.first.value).to be_within(1.second).of(1.hour)
+
+      # the first response should also clear the waiting_since
+      conversation.reload
+      expect(conversation.waiting_since).to be_nil
+    end
+
+    it 'does not reset waiting_since if customer sends another message' do
+      create_customer_message(conversation, created_at: conversation_start_time)
+      conversation.reload
+      expect(conversation.waiting_since).to be_within(1.second).of(conversation_start_time)
+
+      create_customer_message(conversation, created_at: 3.hours.ago)
+      conversation.reload
+      expect(conversation.waiting_since).to be_within(1.second).of(conversation_start_time)
+    end
+
+    it 'records the correct reply_time for subsequent messages' do
+      create_customer_message(conversation, created_at: conversation_start_time)
+      create_agent_message(conversation, created_at: 4.hours.ago)
+      create_customer_message(conversation, created_at: 3.hours.ago)
+
+      create_agent_message(conversation, created_at: 2.hours.ago)
+      reply_events = account.reporting_events.where(name: 'reply_time', conversation_id: conversation.id)
+      expect(reply_events.count).to eq(1)
+      expect(reply_events.first.value).to be_within(1.second).of(1.hour)
+
+      conversation.reload
+      expect(conversation.waiting_since).to be_nil
+    end
+
+    it 'records zero reply time if an agent sends a message after resolution' do
+      create_customer_message(conversation, created_at: conversation_start_time)
+      create_agent_message(conversation, created_at: 4.hours.ago)
+      create_customer_message(conversation, created_at: 3.hours.ago)
+
+      conversation.toggle_status
+      expect(conversation.status).to eq('resolved')
+
+      conversation.toggle_status
+      expect(conversation.status).to eq('open')
+
+      conversation.reload
+      expect(conversation.waiting_since).to be_nil
+
+      create_agent_message(conversation, created_at: 1.hour.ago)
+      # update_waiting_since will ensure that no events were created since the waiting_since was nil
+      # if the event is created it should log zero value, we have handled that in the reporting_event_listener
+      reply_events = account.reporting_events.where(name: 'reply_time', conversation_id: conversation.id)
+      expect(reply_events.count).to eq(0)
+    end
+  end
 end