First of all, ruby 1.8.x does not have SSL working in SMTP, so forget connecting to smtp.gmail.com. Python and perl have it working beautifully. Here’s a quick example, modified slightly from what I found on the net.
#!/usr/bin/env python
# 2008-07-07 17:33
# use this to send a simple mail from your gmail account
import smtplib
import getpass
def prompt(prompt):
[...]
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