[_phred]

Right. If the attack vector is "break SSL" I'm going to try some other attacks first. There's an underlying assumption in the question: my app (and everything else hosted on the box) is safe from XSS, CSRF, injections, and other information leakages. Is it really? How do I know for sure?

And who's to say that your forum server (for example) is just as secure? That could be a foothold into your environment too. And let's not forget social manipulation of your staff and users. Maybe I'll just steal the machine in question, or your laptop.

After I try all those avenues, I'm either finding another target or ramping up for a protracted attack on your SSL connections.

If your site attracts this dedicated of an attack, you'd better get that high paid security consultant. ;)

[dlitz]

The problem with these attacks on SSL is that they're not protracted; They're trivial. Python's httplib doesn't check SSL certificates at all by default, for example, so you just hijack the TCP connection, negotiate SSL, and then you're done.

With libcurl, I think you have to set CURLOPT_SSL_VERIFYHOST to 2. If you set it to TRUE (i.e. 1), it skips part of the certificate check, rendering the whole thing trivially insecure.

Most (all?) crypto libraries have terrible APIs, or have APIs that are far too low-level to be safely used by most developers. SSL shouldn't be the easiest thing to attack, but in the current state of affairs, it often is.