> Personally, I like combining passwords and tokens (the old "what I have and
> what I know" combo). I've been using password-based IMAP transported over
> certificate-based OpenVPN, which does the trick for me.
> 
> I readily acknowledge that my solution isn't really what you're hoping to
> use. Still, it's flexible enough so that all sorts of services that
> traditionally rely on passwords (SMTP AUTH, web services, plus IMAP) can be
> wrapped in a certificate-authenticated connection.


I made this same decision about authenticated IMAP.  I run OpenVPN on
my laptop and it works fine.  It is usually quite good about
recovering when network connectivity comes and goes.  If you're
already using OpenVPN for other things, it is a logical choice to skip
using certificates with each individual service.

The trouble I ran into, though, was with OpenVPN on my Android.  I
can't get it working at all, and I've spent countless hours trying to
debug it (with root access on my phone, sniffing at both ends, etc).
The OpenVPN client connects, successfully authenticates, and then
nothing happens.  No packets at all are transmitted over the
established connection.  It is super frustrating, and no OpenVPN folks
stepped up to help me figure it out.  I'm just hoping with the next
Android phone it will magically work...

Ok, enough venting.


> It has the further benefit that you only need to contact one remote port,
> reducing the chance that a local firewall will become an obstacle to your
> session.

Yup.  You can run OpenVPN on unusual ports (e.g. 53/UDP) that are
often allowed outbound without filtering.  In addition, if you use the
tls-auth option with a UDP port, attackers can't even tell the OpenVPN
service is running on you rserver unless they know the pre-auth
symmetric key. (This is kinda like a group password checked on the
very first packet before certificate authentication is performed.)

tim
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