Two programs:
1. SendEmail: http://caspian.dotconf.net/menu/Software/SendEmail/
2. smtp-cli: http://www.logix.cz/michal/devel/smtp-cli/
I tried SendEmail and it worked fine with gmail TLS SMTP.
The smtp-cli seems to have more features, which also means more complex. :-)
Both programs are written in Perl.
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