lsa-mis · rsmoke · Mar 27, 2025 · Mar 27, 2025 · Mar 27, 2025 · Mar 27, 2025
@@ -2,6 +2,7 @@
 
 class ApplicationMailer < ActionMailer::Base
   prepend_view_path 'app/views/mailers'
-  default from: Rails.application.credentials.dig(:devise, :mailer_sender)
+  default from: Rails.application.credentials.dig(:sendgrid, :mailer_sender),
+          reply_to: 'lsa-evaluate-support@umich.edu'
   layout 'mailer'
 end
@@ -36,9 +36,15 @@ def entry_evaluation_notification(entry, round)
 
     subject = "Evaluation Results for \"#{@entry.title}\" - #{@contest_description.name}"
 
-    mail(
+    # Set mail options - override reply_to if container has a contact email
+    mail_options = {
       to: @user.email,
       subject: subject
-    )
+    }
+
+    # Override reply_to with container's contact_email if present
+    mail_options[:reply_to] = @contact_email if @container.contact_email.present?
+
+    mail(mail_options)
   end
 end
@@ -1,7 +1,11 @@
 class TestMailer < ApplicationMailer
-  def test_email
+  def test_email(recipient_email = nil)
+    @message = 'This is a test email from LSA Evaluate to verify email configuration.'
+    @sender = Rails.application.credentials.dig(:sendgrid, :mailer_sender)
+    @reply_to = 'lsa-wads-rails-email-test@umich.edu'
+
     mail(
-      to: 'test-t68vvtnfc@srv1.mail-tester.com',
+      to: recipient_email || 'lsa-wads-rails-email-test@umich.edu',
       subject: 'Test Email from LSA Evaluate'
     )
   end

@@ -4,8 +4,19 @@
     <meta content='text/html; charset=UTF-8' http-equiv='Content-Type' />
   </head>
   <body>
-    <h1>Test Email from LSA Evaluate</h1>
-    <p>This is a test email to verify email authentication settings.</p>
-    <p>Sent at: <%= Time.current %></p>
+    <h1>Email Configuration Test</h1>
+
+    <p><%= @message %></p>
+
+    <p>This message confirms your email settings are working correctly.</p>
+
+    <h2>Email Configuration:</h2>
+    <ul>
+      <li><strong>From:</strong> <%= @sender %></li>
+      <li><strong>Reply-To:</strong> <%= @reply_to %></li>
+    </ul>
+
+    <p>This is a system-generated email. Please do not reply directly to this message.</p>
+    <p>If you need assistance, please contact <a href="mailto:<%= @reply_to %>"><%= @reply_to %></a>.</p>
   </body>
 </html>
@@ -0,0 +1,13 @@
+Email Configuration Test
+======================
+
+<%= @message %>
+
+This message confirms your email settings are working correctly.
+
+Email Configuration:
+- From: <%= @sender %>
+- Reply-To: <%= @reply_to %>
+
+This is a system-generated email. Please do not reply directly to this message.
+If you need assistance, please contact <%= @reply_to %>.
@@ -0,0 +1,49 @@
+namespace :email do
+  # You can choose whether to queue the email through Sidekiq or send it directly:
+  # For direct delivery:
+  # bin/rails email:test[your@email.com]
+  #
+  # To queue through Sidekiq (add true as a second argument):
+  # bin/rails email:test[your@email.com,true]
+
+  desc 'Send a test email to verify configuration'
+  task :test, [ :email, :queue ] => :environment do |_t, args|
+    recipient = args[:email] || Rails.application.credentials.dig(:sendgrid, :mailer_sender)
+    queue_delivery = args[:queue]&.downcase == 'true'
+
+    if recipient.nil?
+      puts 'ERROR: No recipient email provided and no default contact email configured.'
+      puts 'Usage: rake email:test[recipient@example.com] or rake email:test[recipient@example.com,true] to queue via Sidekiq'
+      exit 1
+    end
+
+    puts "Sending test email to #{recipient}..."
+    begin
+      if queue_delivery
+        # For queued delivery, don't inspect the message before sending
+        puts 'Queuing email delivery through Sidekiq...'
+        TestMailer.test_email(recipient).deliver_later
+        puts 'Email successfully queued in Sidekiq!'
+      else
+        # For direct delivery, we can inspect the message
+        mail = TestMailer.test_email(recipient)
+
+        # Print message details before sending
+        puts 'Message details:'
+        puts "  From: #{mail.from.first || 'Not set'}"
+        puts "  Reply-To: #{mail.reply_to&.first || 'Not set'}"
+        puts "  Subject: #{mail.subject || 'Not set'}"
+        puts 'Headers:'
+        mail.header.fields.each do |field|
+          puts "  #{field.name}: #{field.value}" unless field.name =~ /content-/i
+        end
+
+        mail.deliver_now
+        puts 'Test email sent directly (bypassing Sidekiq)!'
+      end
+    rescue => e
+      puts "ERROR: Failed to send test email: #{e.message}"
+      puts e.backtrace.join("\n")
+    end
+  end
+end