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Right, now, I am configuring Asterisk to send an email when one gets a voicemail.

Due to the firewalls at my school, and securities on our email client, I can't use the ssmtp program directly, but there is a server that I can do it from.

Now, while I can manually telnet a test email to wherever, is there a way I could cat a file to the server and email it to an address of my choosing?

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You can setup your mailer(postfix or sendmail) to send using different port and setup mailer on other (external) system to listen on other port.

Asterisk email can use external script for email delivery, script can do whatever you want.

/etc/asterisk/voicemail.conf

externnotify=/usr/bin/myapp

OR

mailcmd=/usr/bin/myscript

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