unable to send email via smtp over ssl

Question

i am writing a ruby script to send email using 'mail' gem.

and my smtp settings on my local machine:

mailer_options:
    address: smtp.gmail.com
    port: 587
    domain: gmail.com
    user_name: example@gmail.com
    password: example_password
    authentication: :login
    enable_starttls_auto: true
    ssl: true

when i try to send the email with the above smtp settings i get the following exception:---

/opt/rbenv/versions/2.0.0-p247/lib/ruby/2.0.0/net/smtp.rb:585:in 'connect': SSL_connect returned=1 errno=0 state=SSLv2/v3 read server hello A: unknown protocol (OpenSSL::SSL::SSLError)

i tried installing ssl certificate by command

openssl s_client -connect gmail.com:443

but it does not help, thanks for any comments and answer.

Answer 1

Port 587 starts out plain text, and then "upgrades" to ssl via starttls if you want smtp from the start to use ssl, then you need to use port 465.

so either of these should fix your issue.

Remove enable_starttls_auto and set the port to 465

or

Remove ssl: true and rely on starttls to upgrade your connection to ssl