Re: [TLS] Asking the browser for a different certificate

[Marsh Ray <[e-mail]>]

On 3/29/2010 12:45 PM, Martin Rex wrote:
> Marsh Ray wrote:
>>
>> Consider an attacker passively sniffing public wifi in a coffee shop
>> near a targeted organization. Now he sees who has his smart card in the
>> reader and activated.
> 
> To me this sounds extremely farfetched.

Really? It's pretty standard stuff

http://www.google.com/search?q=wifi+penetration+testing

> The ClientHello also "leaks" the maximum protocol_version that your
> client supports, the cipher_suites and compression algs your client
> is willing to use.

Yes, there are lots of ways existing TLS clients can be fingerprinted.

> The reason why a client may be sending that information may be manyfold,
> not necessarily a presence of a Smartcard.

True.

Still, as more TLS extensions get used in practice, I think each
extension's potential for info leakage needs to be well understood and
well documented.

> A client could implement
> a caching of a users decision to present a client cert, e.g. on a
> per-server basis, or for a specific amount of time (for the next X hours).
> 
> For those users that use SmartCards enabled for TLS client cert
> authentication, you will see their entire certificate flying by
> in the clear in the regular TLS handshake when they connect
> to the TLS server for which they plugged their SmartCard in the
> first place.

As you know, many web servers request the client cert under an existing
encrypted session via renegotiation specifically because they don't want
that to happen.

Passing the TLS record content type in plaintext (so the renegotiation
becomes visible to a passive observer) is another info leak that would
be good to fix.

> And would you make your client include a "certificate URL extension"
> even when the client does not have a client certificate.  Well, maybe
> -- if you are the CIA and ordering your constant daily batch of pizzas.  :)

A. I think everyone should be able to order their pizzas over TLS! :-)

B. All cryptography used to be super secret spy stuff. But the trend has
been only accelerating over the years that data security practices that
were formerly considered paranoid are increasingly necessary for
business to resist corporate espionage and individuals to retain some
online privacy from intrusive ISPs and governments.

> Maybe you should not use any secure authentication protocols like
> Kerberos or TLS if you want to entirely hide that fact, that you possess
> secure client credentials.

Yep, those with the highest security requirements are better off
connecting only through a VPN, or not remotely at all. To some degree
this can be considered a failure of the existing security protocols.

Your "I don't have any client certs" extension suggestion is probably
not that big a deal, it's hard to tell. I think the deeper problem is
that TLS client authentication requires the client to transmit and sign
with his cert before he is able to strongly authenticate the server.

- Marsh