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I run ProFTPd with TLS authentication on my Debian Lenny server. My problem is that despite of the fact that my users connect chrooted, one of my friends had root privileges after logging in form a Macintosh and could browse the root directory, too.
Not to split hairs, but to steer the discussion in the right direction you might refer to your service as FTPS (FTP over SSL/TLS, not to be confused with SFTP, which is totally different).
This is an application layer problem, so crank up those debug logs and review the behavior you see for his particular client. Also, talk through things with the user from his perspective to ensure that he is really seeing "/", and not just his perception of "/" (which is of course his chrooted directory).
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