Add instructor email notifications for pending requests

app/controllers/course_settings_controller.rb

@@ -71,7 +71,9 @@ def course_settings_params
       :email_subject,
       :email_template,
       :enable_slack_webhook_url,
-      :slack_webhook_url
+      :slack_webhook_url,
+      :pending_notification_frequency,
+      :pending_notification_email
     )
   end
 

app/javascript/controllers/course_settings_controller.js

@@ -1,12 +1,13 @@
 import { Controller } from "@hotwired/stimulus"
 
 export default class extends Controller {
-  static targets = ["emailField", "tab", "gradescopeField", "slackWebhookField"];
+  static targets = ["emailField", "tab", "gradescopeField", "slackWebhookField", "pendingNotificationEmail"];
 
   connect() {
     this.toggleEmailFields();
     this.toggleSlackWebhookField();
     this.toggleGradescopeFields();
+    this.togglePendingNotificationEmail();
 
     const gradescopeToggle = document.getElementById('enable-gradescope');
     if (gradescopeToggle) {
@@ -53,6 +54,15 @@ export default class extends Controller {
     }
   }
 
+  togglePendingNotificationEmail() {
+    const frequencySelect = document.getElementById('pending-notification-frequency');
+    const emailField = document.getElementById('pending-notification-email');
+
+    if (frequencySelect && emailField) {
+      emailField.disabled = !frequencySelect.value;
+    }
+  }
+
   updateUrlParam(event) {
     const tabName = event.currentTarget.dataset.tab;
     const url = new URL(window.location);

app/jobs/pending_requests_notification_job.rb

@@ -0,0 +1,32 @@
+class PendingRequestsNotificationJob < ApplicationJob
+  queue_as :default
+
+  def perform(frequency)
+    CourseSettings.with_pending_notifications(frequency).includes(:course).find_each do |cs|
+      course = cs.course
+      pending_count = Request.where(course_id: course.id, status: 'pending').count
+      next if pending_count.zero?
+
+      requests_url = "#{ENV.fetch('APP_HOST', nil)}/courses/#{course.id}/requests"
+
+      EmailService.send_email(
+        to: cs.pending_notification_email,
+        from: ENV.fetch('DEFAULT_FROM_EMAIL'),
+        reply_to: cs.reply_email.presence || ENV.fetch('DEFAULT_FROM_EMAIL'),
+        subject_template: '{{pending_count}} Pending Extension Request{{plural}} - {{course_code}}',
+        body_template: "Hello,\n\nYou have {{pending_count}} pending extension request{{plural}} " \
+                       "in {{course_name}} ({{course_code}}).\n\n" \
+                       "Please review them at: {{requests_url}}\n\n" \
+                       "Thank you,\nFlextensions",
+        mapping: {
+          'pending_count' => pending_count.to_s,
+          'plural' => pending_count == 1 ? '' : 's',
+          'course_name' => course.course_name,
+          'course_code' => course.course_code,
+          'requests_url' => requests_url
+        },
+        deliver_later: false
+      )
+    end
+  end
+end

app/models/course_settings.rb

@@ -48,12 +48,25 @@ class CourseSettings < ApplicationRecord
     {{course_name}} Staff
   LIQUID
 
+  VALID_NOTIFICATION_FREQUENCIES = %w[daily weekly].freeze
+
   belongs_to :course
 
+  before_validation -> { self.pending_notification_frequency = nil if pending_notification_frequency.blank? }
+  before_validation -> { self.pending_notification_email = nil if pending_notification_email.blank? }
   before_save :ensure_system_user_for_auto_approval
+  before_save -> { self.pending_notification_email = nil if pending_notification_frequency.nil? }
   validate :gradescope_url_is_valid, if: :enable_gradescope?
+  validates :pending_notification_frequency, inclusion: { in: VALID_NOTIFICATION_FREQUENCIES }, allow_nil: true
+  validates :pending_notification_email, presence: true, format: { with: /\A[^@\s]+@[^@\s]+\z/ },
+                                         if: -> { pending_notification_frequency.present? }
   after_save :create_or_update_gradescope_link
 
+  scope :with_pending_notifications, ->(frequency) {
+    where(pending_notification_frequency: frequency)
+    .where.not(pending_notification_email: [nil, ''])
+  }
+
   def ensure_system_user_for_auto_approval
     # Create the system user if auto-approval is being enabled
     return unless enable_extensions && auto_approve_days.to_i.positive?

app/views/courses/edit.html.erb

@@ -180,6 +180,34 @@
                                     </div>
                                 </div>
 
+                                <div class="mb-3 row border-bottom pb-3">
+                                    <label for="pending-notification-frequency" class="col-sm-4 col-form-label">Pending Request Notifications</label>
+                                    <div class="col-sm-8">
+                                        <%= select_tag 'course_settings[pending_notification_frequency]',
+                                                       options_for_select(
+                                                         [['No notifications', ''], ['Daily', 'daily'], ['Once weekly (Fridays)', 'weekly']],
+                                                         @course.course_settings&.pending_notification_frequency
+                                                       ),
+                                                       class: 'form-select',
+                                                       id: 'pending-notification-frequency',
+                                                       data: { action: 'change->course-settings#togglePendingNotificationEmail' } %>
+                                    </div>
+                                </div>
+
+                                <div class="mb-3 row border-bottom pb-3">
+                                    <label for="pending-notification-email" class="col-sm-4 col-form-label">Notification Email</label>
+                                    <div class="col-sm-8">
+                                        <%= email_field_tag 'course_settings[pending_notification_email]',
+                                                          @course.course_settings&.pending_notification_email,
+                                                          class: 'form-control',
+                                                          id: 'pending-notification-email',
+                                                          placeholder: 'instructor@berkeley.edu',
+                                                          data: { course_settings_target: 'pendingNotificationEmail' },
+                                                          disabled: @course.course_settings&.pending_notification_frequency.blank? %>
+                                        <div class="form-text">Weekly notifications are sent on Fridays at 5:00 PM PT.</div>
+                                    </div>
+                                </div>
+
                                 <div class="mb-3">
                                     <div class="text-start">
                                         <% if @course.course_settings&.enable_extensions %>

db/migrate/20260406175234_add_pending_notification_to_course_settings.rb

@@ -0,0 +1,10 @@
+class AddPendingNotificationToCourseSettings < ActiveRecord::Migration[7.2]
+  def change
+    safety_assured do
+      change_table :course_settings, bulk: true do |t|
+        t.string :pending_notification_frequency, default: nil
+        t.string :pending_notification_email, default: nil
+      end
+    end
+  end
+end

db/schema.rb

@@ -10,7 +10,7 @@
 #
 # It's strongly recommended that you check this file into your version control system.
 
-ActiveRecord::Schema[7.2].define(version: 2025_10_01_192900) do
+ActiveRecord::Schema[7.2].define(version: 2026_04_06_175234) do
   # These are extensions that must be enabled in order to support this database
   enable_extension "plpgsql"
 
@@ -102,6 +102,8 @@
     t.boolean "enable_slack_webhook_url"
     t.boolean "enable_gradescope", default: false
     t.string "gradescope_course_url"
+    t.string "pending_notification_frequency"
+    t.string "pending_notification_email"
     t.index ["course_id"], name: "index_course_settings_on_course_id"
   end
 

lib/tasks/notifications.rake

@@ -0,0 +1,9 @@
+namespace :notifications do
+  desc 'Send pending request digest emails (usage: rake notifications:send_pending_digests[daily])'
+  task :send_pending_digests, [:frequency] => :environment do |_t, args|
+    frequency = args[:frequency]
+    abort 'Usage: rake notifications:send_pending_digests[daily|weekly]' unless %w[daily weekly].include?(frequency)
+
+    PendingRequestsNotificationJob.perform_now(frequency)
+  end
+end

spec/controllers/course_settings_controller_spec.rb

@@ -118,6 +118,75 @@
     end
   end
 
+  describe 'pending notification params' do
+    before do
+      session[:user_id] = instructor.canvas_uid
+      UserToCourse.create!(user: instructor, course: course, role: 'instructor')
+      allow_any_instance_of(Course).to receive(:user_role).with(instructor).and_return('instructor')
+      CourseSettings.create!(course: course, enable_extensions: true)
+    end
+
+    it 'persists pending notification settings' do
+      post :update, params: {
+        course_id: course.id,
+        course_settings: {
+          pending_notification_frequency: 'daily',
+          pending_notification_email: 'prof@berkeley.edu'
+        },
+        tab: 'general'
+      }
+
+      settings = CourseSettings.find_by(course_id: course.id)
+      expect(settings.pending_notification_frequency).to eq('daily')
+      expect(settings.pending_notification_email).to eq('prof@berkeley.edu')
+    end
+
+    it 'normalizes blank frequency to nil' do
+      post :update, params: {
+        course_id: course.id,
+        course_settings: {
+          pending_notification_frequency: '',
+          pending_notification_email: ''
+        },
+        tab: 'general'
+      }
+
+      settings = CourseSettings.find_by(course_id: course.id)
+      expect(settings.pending_notification_frequency).to be_nil
+    end
+
+    it 'clears stored email when frequency is set to blank' do
+      settings = CourseSettings.find_by(course_id: course.id)
+      settings.update!(pending_notification_frequency: 'daily', pending_notification_email: 'prof@berkeley.edu')
+
+      post :update, params: {
+        course_id: course.id,
+        course_settings: {
+          pending_notification_frequency: '',
+          pending_notification_email: ''
+        },
+        tab: 'general'
+      }
+
+      settings.reload
+      expect(settings.pending_notification_frequency).to be_nil
+      expect(settings.pending_notification_email).to be_nil
+    end
+
+    it 'shows validation errors for invalid email with frequency set' do
+      post :update, params: {
+        course_id: course.id,
+        course_settings: {
+          pending_notification_frequency: 'daily',
+          pending_notification_email: 'not-an-email'
+        },
+        tab: 'general'
+      }
+
+      expect(flash[:alert]).to include('Failed to update course settings:')
+    end
+  end
+
   describe 'pending requests count' do
     let(:assignment) do
       # Create necessary related objects for Request

spec/factories/course_settings.rb

@@ -35,5 +35,15 @@
     association :course
     enable_extensions { true }
     auto_approve_days { 0 }
+
+    trait :with_daily_notifications do
+      pending_notification_frequency { 'daily' }
+      pending_notification_email { 'instructor@example.com' }
+    end
+
+    trait :with_weekly_notifications do
+      pending_notification_frequency { 'weekly' }
+      pending_notification_email { 'instructor@example.com' }
+    end
   end
 end

spec/jobs/pending_requests_notification_job_spec.rb

@@ -0,0 +1,86 @@
+require 'rails_helper'
+
+RSpec.describe PendingRequestsNotificationJob, type: :job do
+  let(:course) { create(:course, canvas_id: 'notif_123', course_name: 'CS 101', course_code: 'CS101') }
+  let(:student) { create(:user, canvas_uid: 'stu_notif_1', email: 'student_notif@example.com', name: 'Student') }
+  let(:lms) { Lms.first }
+  let(:course_to_lms) { CourseToLms.create!(course: course, lms: lms, external_course_id: 'ext_123') }
+  let(:assignment) do
+    Assignment.create!(
+      name: 'HW1',
+      course_to_lms: course_to_lms,
+      due_date: 3.days.from_now,
+      external_assignment_id: 'asgn_notif_1',
+      enabled: true
+    )
+  end
+
+  before do
+    ActionMailer::Base.delivery_method = :test
+    ActionMailer::Base.deliveries.clear
+    allow(ENV).to receive(:fetch).and_call_original
+    allow(ENV).to receive(:fetch).with('DEFAULT_FROM_EMAIL').and_return('flextensions@berkeley.edu')
+    allow(ENV).to receive(:fetch).with('APP_HOST', nil).and_return('http://localhost:3000')
+  end
+
+  describe '#perform' do
+    it 'sends email when course has matching frequency and pending requests' do
+      course.course_settings.update!(pending_notification_frequency: 'daily', pending_notification_email: 'prof@example.com')
+      Request.create!(course: course, assignment: assignment, user: student, status: 'pending',
+                      reason: 'Need more time', requested_due_date: 5.days.from_now)
+
+      expect { described_class.perform_now('daily') }.to change { ActionMailer::Base.deliveries.count }.by(1)
+
+      mail = ActionMailer::Base.deliveries.last
+      expect(mail.to).to eq(['prof@example.com'])
+      expect(mail.subject).to include('1 Pending Extension Request')
+      expect(mail.subject).to include('CS101')
+      expect(mail.body.encoded).to include("http://localhost:3000/courses/#{course.id}/requests")
+    end
+
+    it 'skips courses with zero pending requests' do
+      course.course_settings.update!(pending_notification_frequency: 'daily', pending_notification_email: 'prof@example.com')
+
+      expect { described_class.perform_now('daily') }.not_to(change { ActionMailer::Base.deliveries.count })
+    end
+
+    it 'only sends to courses matching the given frequency' do
+      course.course_settings.update!(pending_notification_frequency: 'weekly', pending_notification_email: 'prof@example.com')
+      Request.create!(course: course, assignment: assignment, user: student, status: 'pending',
+                      reason: 'Need more time', requested_due_date: 5.days.from_now)
+
+      expect { described_class.perform_now('daily') }.not_to(change { ActionMailer::Base.deliveries.count })
+    end
+
+    it 'pluralizes correctly for multiple pending requests' do
+      course.course_settings.update!(pending_notification_frequency: 'daily', pending_notification_email: 'prof@example.com')
+      2.times do |i|
+        Request.create!(course: course, assignment: assignment,
+                        user: create(:user, canvas_uid: "stu_multi_#{i}", email: "stu_multi_#{i}@example.com"),
+                        status: 'pending', reason: 'Need time', requested_due_date: 5.days.from_now)
+      end
+
+      described_class.perform_now('daily')
+
+      mail = ActionMailer::Base.deliveries.last
+      expect(mail.subject).to include('2 Pending Extension Requests')
+    end
+
+    it 'sends separate emails to multiple courses' do
+      course.course_settings.update!(pending_notification_frequency: 'daily', pending_notification_email: 'prof1@example.com')
+      Request.create!(course: course, assignment: assignment, user: student, status: 'pending',
+                      reason: 'Need time', requested_due_date: 5.days.from_now)
+
+      other_course = create(:course, canvas_id: 'notif_456', course_name: 'CS 201', course_code: 'CS201')
+      other_ctlms = CourseToLms.create!(course: other_course, lms: lms, external_course_id: 'ext_456')
+      other_assignment = Assignment.create!(name: 'HW2', course_to_lms: other_ctlms, due_date: 3.days.from_now,
+                                            external_assignment_id: 'asgn_notif_2', enabled: true)
+      other_course.course_settings.update!(pending_notification_frequency: 'daily', pending_notification_email: 'prof2@example.com')
+      other_student = create(:user, canvas_uid: 'stu_notif_2', email: 'stu_notif_2@example.com')
+      Request.create!(course: other_course, assignment: other_assignment, user: other_student, status: 'pending',
+                      reason: 'Need time', requested_due_date: 5.days.from_now)
+
+      expect { described_class.perform_now('daily') }.to change { ActionMailer::Base.deliveries.count }.by(2)
+    end
+  end
+end