I would be curious to know what kind of vulnerabilities the latest version of Eudora (7.1.0.9 I think) has. With how old it is (2006), surely there are several critical vulnerabilities, but all I could find when looking online is that an IMAP server or SMTP server can execute arbitrary code, which doesn't seem likely to cause a real problem, because I wouldn't expect Google, Yahoo, Microsoft, etc. to use this trick.

The article links to a vulnerability from 1998, which I expect is already fixed in the versions of Eudora people still use.

I agree it would probably be easy for AI to find exploitable bugs though.