STUMPED: Setting up OpenVPN server on FreeBSD (self.freebsd)

Fongaboo freebsd at
Mon Sep 4 18:10:45 UTC 2017

Sorry I faded away there... This issue dragged on long enough that life 
started setting different priorities. I got a bare metal machine to try 
it on, but that brought further complexities... as the ports/pkgs for 
OpenVPN and EasyRSA greatly differed between FreeBSD 10.2 and 11.1.

I put this on the back burner for now, as I was able to set up SSH tunnel 
to the bare metal box and then use an app called Proxifier to route my 
traffic on my PC and Mac.

But it brings to mind a question... Why are SSH tunnels pretty turnkey to 
setup, and OpenVPN takes so much configuration (of both the app and the 
host OS's networking)? When I tunnel SSH, it 'just works' and my client 
machine uses the FreeBSD machine's gateway as its own.

Thank you to everyone that provided very meaningful troubleshooting. I 
plan to dig back into this when I have more time.

On Mon, 28 Aug 2017, Ultima wrote:

>> It should do, though I'm not familiar with the AWS setup you're using re
>> inside and outside interfaces, whether bridging as well, etc.  I think
>> Richard (Ultima) has and can provide much more useful advice about that.
> Want to note that I have zero experience with ipfw, natd as well as Amazon
> AWS. My knowledge is assuming that FreeBSD pf and OpenVPN will run as
> they would on a bare metal. Have used digital ocean with a similar
> configuration
> successfully as well.
> Hope this helps,
> Richard Gallamore
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