Fix SMTP TLS failures from openssl_verify_mode Symbol conversion

Pass openssl_verify_mode as a String so the mail gem can map it to
OpenSSL constants, wire PWP__MAIL__SMTP_STARTTLS to enable_starttls,
and only report TestMailer success after delivery.

Fixes #4005

Author: Peter Giacomo Lombardo

app/mailers/test_mailer.rb

@@ -1,4 +1,6 @@
 class TestMailer < ApplicationMailer
+  after_deliver :announce_test_email_success, only: :send_test_email
+
   def send_test_email(email)
     puts ""
     puts "--> Configured FROM: address: '#{Settings.mail.mailer_sender}'"
@@ -64,17 +66,21 @@ def send_test_email(email)
 
     puts ""
     puts "--> Attempting to send a test email to #{email}..."
-    mail(to: email,
-      subject: "Test Email from Password Pusher",
-      body: "⭐  If you are reading this, sending email works! ⭐ ")
-
-    puts "--> ✅   It seems that the Email was accepted by the SMTP server!  Check destination inbox for the test email."
     puts ""
-
     puts "--> If you see an error, please paste this output into a GitHub issue for help."
     puts "  --> Make sure that no sensitive data is included."
     puts "  --> https://github.com/pglombardo/PasswordPusher/issues/new/choose"
+    puts ""
 
+    mail(to: email,
+      subject: "Test Email from Password Pusher",
+      body: "⭐  If you are reading this, sending email works! ⭐ ")
+  end
+
+  private
+
+  def announce_test_email_success
+    puts "--> ✅   It seems that the Email was accepted by the SMTP server!  Check destination inbox for the test email."
     puts ""
   end
 end

config/defaults/settings.yml

@@ -337,7 +337,7 @@ mail:
 
   # When using TLS, you can set how OpenSSL checks the certificate. This is
   # useful if you need to validate a self-signed and/or a wildcard certificate.
-  # This can be one of the OpenSSL verify constants, :none or :peer
+  # Must be a string name of an OpenSSL verify constant: 'none' or 'peer'
   # Environment Variable Override: PWP__MAIL__SMTP_OPENSSL_VERIFY_MODE='none'
   # smtp_openssl_verify_mode: 'peer'
 

config/environments/production.rb

@@ -163,16 +163,19 @@
       config.action_mailer.smtp_settings[:password] = Settings.mail.smtp_password
     end
 
+    # Pass a String ("none" / "peer"). The mail gem maps strings to OpenSSL::SSL::VERIFY_*
+    # constants; a Symbol like :none raises TypeError during TLS handshake.
     if !Settings.mail.smtp_openssl_verify_mode.nil?
-      config.action_mailer.smtp_settings[:openssl_verify_mode] = Settings.mail.smtp_openssl_verify_mode.to_sym
+      config.action_mailer.smtp_settings[:openssl_verify_mode] = Settings.mail.smtp_openssl_verify_mode.to_s
     end
 
     if !Settings.mail.smtp_enable_starttls_auto.nil?
       config.action_mailer.smtp_settings[:enable_starttls_auto] = Settings.mail.smtp_enable_starttls_auto
     end
 
-    if !Settings.mail.smtp_enable_starttls.nil?
-      config.action_mailer.smtp_settings[:enable_starttls] = Settings.mail.smtp_enable_starttls
+    # settings.yml / PWP__MAIL__SMTP_STARTTLS maps to smtp_starttls
+    if !Settings.mail.smtp_starttls.nil?
+      config.action_mailer.smtp_settings[:enable_starttls] = Settings.mail.smtp_starttls
     end
   end
 

config/settings.yml

@@ -337,7 +337,7 @@ mail:
 
   # When using TLS, you can set how OpenSSL checks the certificate. This is
   # useful if you need to validate a self-signed and/or a wildcard certificate.
-  # This can be one of the OpenSSL verify constants, :none or :peer
+  # Must be a string name of an OpenSSL verify constant: 'none' or 'peer'
   # Environment Variable Override: PWP__MAIL__SMTP_OPENSSL_VERIFY_MODE='none'
   # smtp_openssl_verify_mode: 'peer'