email - Rails 4 Net::SMTPAuthenticationError: 535 #5.7.0 Authentication failed

Question

I'm building a email list for a student organization at my University. The organization has around 6000 members and to avoid costs I've received permission to use the schools emails servers and they have created an account for me.

I have tested the the account using my mail client and everything seems to be working fine, but when I try to send through my Rails 4 app I get the error:

Net::SMTPAuthenticationError: 535 #5.7.0 Authentication failed

I have it configured like so:

application.rb

config.action_mailer.smtp_settings = 
{
    :address   => "smtp.school.edu",
    :port      => 25, 
    :enable_starttls_auto => true, 
    :user_name => "account@school.edu",
    :password  => "mypassword", 
    :authentication => 'login',
    :domain => 'http://myapp.herokuapp.com/' 
}

Again the credentials are all correct, I have tested it through my mail client and have also sat down with the server admin to confirm everything looks right in my configuration as far as port and credentials.

I've been told the smtp server is "wide open to the public" and there is nothing blocking a connection and we have checked their logs and they haven't even seen an attempt to connect from my app.

Anyone have any clue what is going wrong here? Is there some setting I dont know about that could be off?

Answer 1

Try adding openssl_verify_mode => 'none' to your action mailer settings:

config.action_mailer.smtp_settings = 
{
    :address   => "smtp.school.edu",
    :port      => 25, 
    :enable_starttls_auto => true, 
    :user_name => "account@school.edu",
    :password  => "mypassword", 
    :authentication => 'login',
    :domain => 'http://myapp.herokuapp.com/',
    :openssl_verify_mode => 'none'
}

Granted, we are using Rails 3, but this worked for me. The issue for us was that our certificates are self-signed and the library Rails uses considers that to be a problem. Here is an article that talks about the option.