[Tutor] How to send email from a gmail a/c using smtp when port 587(smtp) is blocked

[Marc Tompkins]

On Tue, Sep 11, 2012 at 3:27 PM, ashish makani <ashish.makani at gmail.com>wrote:

> Marc,
> your 3rd point,
>
>> you could establish a VPN tunnel to some server outside of the
>> university's network and send from port 587 on THAT machine.  Complicated,
>> weird, and not horribly secure.  But doable.
>
> Could you point me to a good link/resource on how to do this ?
>

Hmmm... having said that, I'm puzzling over the simplest way to actually do
it.  First idea (based on stuff I've set up in the past):
-  at your outside location, set up a VPN endpoint/router, with your SMTP
server sitting behind it
-  on your computer inside the university's network, install a VPN client
and establish the tunnel before launching your script

I am very fond of pfSense <http://www.pfsense.org> as a router/firewall; it
has OpenVPN <http://openvpn.net/index.php/open-source.html> support baked
in, and if you install the "OpenVPN Client Export Utility" package (a
single click, once pfSense is installed) it will export a ready-made
configuration file for the remote machine.

Two things:
-  as I said, this is a complicated and weird way to do this, although it's
probably more secure than I thought when I first mentioned it.  But it's
probably NOT the best way to go about it.
-  somebody out there, with better Python chops than I, will no doubt point
out a way to do the same thing all in Python.  Even if this were the proper
approach, I'm not guaranteeing it's the best way to implement it.

If you do decide to go this way, you'll need a machine (it could even be a
virtual machine, but I find it much simpler to use an old junker PC with
two network cards) to run pfSense, and of course an SMTP server.
I'd just like to add a quick endorsement for pfSense in general, by the way
- it's free and open-source, but I have yet to find anything it doesn't do,
and do well, compared to Cisco/Juniper/SonicWall/etc.  Of course, the old
junker PC you run it on needs to be in decent working condition - stable
power supply (and power!), no flaky memory or unstable NICs - but it
doesn't need to be very new or very powerful.
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