(Ruby) Getting Net::SMTP working with Gmail…?

Question

Does anyone have any quality (and up-to-date) information regarding sending mail via Gmail using Ruby\'s Net::SMTP? I\'ve seen several examples -- most dating from 2007 to

Answer 1

Are you connecting to smtp.gmail.com port 465 I am assuming? .

openssl s_client -connect smtp.gmail.com:587

CONNECTED(00000003) 8298:error:140770FC:SSL routines:SSL23_GET_SERVER_HELLO:unknown protocol:s23_clnt.c:601:

The error looks very similar to yours. The following command does work:

 openssl s_client  -starttls smtp -connect smtp.gmail.com:587

So I think what is happening is that you do not have STARTTLS support enabled. I am not sure how to do it in ruby buy what I did find out is that the action_mailer_tls plugin allows this by patching Net::SMTP. As of Ruby 1.8.7, Net::SMTP has this support built-in.

If you are using Ruby < 1.8.7 here is the patch.