> Well first of all if you don't use a real certificate 
> authority, but install a self generated certificate, then 
> using the man in the middle attack, the other pc can install 
> a self generated cert, and you wouldn't know it, since all 
> you would get is a warning. This of course requires dns/arp 
> poisoning to implement.

Yes, self-signed certificates do not provide the validation that comes with
a certificate signed by a trusted certificate authority. That is one of the
obvious limitations of self-signed certificates, I would think.

> If you use a real certificate from one of the certificate 
> authorities, the man in the middle can do 1 of 2 things 
> (after they've done the dns/arp poisoning).  
> 
> 1.  Steal the certificate from your server and install it on 
> theirs 2.  Somehow get access to make changes to the domain 
> registration or to read the domain registration contact 
> emails, and then buy their own certificate.

Note that I didn't say it couldn't be done. I said it would not be trivial.
I think you've just demonstrated that, with your explanation. Multiple
security vulnerabilities would need to exist. And if I could steal the
certificate from your server, I doubt I'd need to go to all this trouble, as
I'd obviously have some sort of control over one of the two vulnerable SSL
endpoints, and I could probably just query the databases, etc, directly
anyway.

> The scenario you've presented where the user goes to 'bad' 
> site and the 'bad' site accesses the 'good' site as a proxy, 
> the 'bad' site administrator can buy the certificate for 
> their domain name, and no warning will be issued.  In your 
> example, I would buy a certificate for tra1ning.fugleaf.com 
> and trick the user into going there.

This is certainly more viable, as the current success of phishing exploits
demonstrates. However, within the context of an intranet environment - the
environment described by the original poster - this is much less likely to
succeed. Most employees presumably know the domain name of their employer,
for example.

Dave Watts, CTO, Fig Leaf Software
http://www.figleaf.com/

Fig Leaf Software provides the highest caliber vendor-authorized
instruction at our training centers in Washington DC, Atlanta,
Chicago, Baltimore, Northern Virginia, or on-site at your location.
Visit http://training.figleaf.com/ for more information!

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