Q: opportunistic email encryption

2002-11-22 Thread Eugen Leitl
Question: if you control the traffic layer you can easily disrupt
opportunistic encryption (STARTTLS  Co) by killing public key exchange,
or even do a MITM.

Is there any infrastructure in MTAs for public key caching, and admin
notification if things look fishy? (Fishy: a host which used to do PKI 
with you suddenly says it can't, or its key differs from key you cached).

(Okay, it's unlikely, but maybe people have been anticipating this).




Re: Q: opportunistic email encryption

2002-11-22 Thread Adam Shostack
On Fri, Nov 22, 2002 at 09:23:57PM +0100, Eugen Leitl wrote:
| Question: if you control the traffic layer you can easily disrupt
| opportunistic encryption (STARTTLS  Co) by killing public key exchange,
| or even do a MITM.
| 
| Is there any infrastructure in MTAs for public key caching, and admin
| notification if things look fishy? (Fishy: a host which used to do PKI 
| with you suddenly says it can't, or its key differs from key you cached).
| 
| (Okay, it's unlikely, but maybe people have been anticipating this).

Not that we've found.  I did a little experimenting with huge SSL
session timeouts and high log levels, but saw nothing logged that
indicated that someone who should have had a key didn't.

While what you propose is useful enough that I spent time looking for
it, lets not let the best become the enemey of the good.  Needing to
disrupt a network connection is a huge cost for an Eve who prefers to
avoid detection.  Not an unpayable one, but not to be ignored.

Adam

-- 
It is seldom that liberty of any kind is lost all at once.
   -Hume




Re: Q: opportunistic email encryption

2002-11-22 Thread Eric Murray
On Fri, Nov 22, 2002 at 09:23:57PM +0100, Eugen Leitl wrote:
 Question: if you control the traffic layer you can easily disrupt
 opportunistic encryption (STARTTLS  Co) by killing public key exchange,
 or even do a MITM.

An attacker can prevent opportunistic STARTTLS by modifying
the STARTTLS tag in SMTP.

 Is there any infrastructure in MTAs for public key caching, and admin
 notification if things look fishy? (Fishy: a host which used to do PKI 
 with you suddenly says it can't, or its key differs from key you cached).

ssh does this.


Eric




Q: opportunistic email encryption

2002-11-22 Thread Eugen Leitl
Question: if you control the traffic layer you can easily disrupt
opportunistic encryption (STARTTLS  Co) by killing public key exchange,
or even do a MITM.

Is there any infrastructure in MTAs for public key caching, and admin
notification if things look fishy? (Fishy: a host which used to do PKI 
with you suddenly says it can't, or its key differs from key you cached).

(Okay, it's unlikely, but maybe people have been anticipating this).