On 2013-04-06 at 13:48 +0000, Edward Ned Harvey (lopser) wrote:
> If you're using AES-256 and keys (not just passwords) then no, they
> can't sniff it.  No more than they could sniff your VPN traffic on the
> public internet.

AES is not magic fairy dust which magically makes things secure, it's a
component of a larger system.  What we see is that even when the
protocols are designed by experts, decades later we're still shaking out
the flaws.  WiFi crypto started from a very bad place and managed to get
a bit better with WPA2.  It would be foolhardy to assume that no new
attacks will be found.

 AES in TLS1.2 != AES in <other-system>

So, as sysadmins, our task is to set things up to achieve the business
objectives while being fairly resilient, finding a balance between
"perfect" and "works well enough without getting in peoples' way".

WiFi security has taught us that changes take a minimum of a half decade
to propagate, as fixes have to be at the hardware or firmware level,
can't be applied to all devices (so lifecycle replacement is part of the
migration strategy) and that parts will be implemented badly on some
devices and you're left trying to argue for security when a VP is
insisting on connecting their broken device.

By contrast, VPN software is software; it can be replaced, it can be
chosen, there are competing technologies.  You can use something like
VPN Tracker on MacOS to avoid hardware vendors' crappy drivers.

Architecturally, designing your security to be based on the component
you can best control, manage, update/replace and generally "own" means
that you have the authority/control to go with the responsibility.

Of course, a single point of failure of the VPN gateway is also bad.

I feel the decisions should be around designing to avoid SPoF, not
around an assumption that a layer you can't control or replace will
always be considered strong enough.

-Phil
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