Just some notes about what works and what is simple.
Works and is simple
http://www.debianadmin.com/how-to-sendemail-from-the-command-line-using-a-gma...
You can install sendEmail via Synaptic in Ubuntu but you will need to also install
- libio-socket-ssl-perl
- libnet-ssleay-perl
- perl
You can, of course, just tell Synaptic to do that. You can also do it all from the command line:
$ sudo apt-get install sendemail libio-socket-ssl-perl libnet-ssleay-perl perl
Caveats and questions
sendEmail can use tls authentication but presumably this does not mean that the actual traffic is secure. Of course email is normally transmitted in the clear anyway so this might not be a problem; however, if you are using this to backup confidential files to your gmail account you should try to use secure sockets to secure the connection against eavesdroppers. And, especially in the light of recent reports of a Google employee snooping on email, you should encrypt the files themselves.
So the question: can sendEmail use SSL?
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