I wrote a perl obfuscator back in 2002 for use on a project at work. Jokes about perl's already obfuscated syntax aside, we had evaluated a number of alternatives including perlcc and perl2exe, but both failed to meet our needs for reasons I can't remember some 5 years later. Source filtering hacks such as Acme::Bleach were ruled out because they are trivially reversible.
Anyway, I finally got sign-off by my manager back in May of 2006 to open source our obfuscator under the GPL. It has been up on my public CVS repository ever since then but I just now finally got around to putting together its own site. That said, it appears the state of the art (such that it is) has advanced considerably since I first developed this tool in 2002. For example, while I have not evaluated it yet, Stunnix appears to have put together a superior perl obfuscator. I suspect that if Stunnix's product had been around in 2002, I would have never had to delve into the deepest darkest recesses of TIMTOWTDI to write our own.
If I had to do it all over again, I would probably have used Syntax::Highlight::Perl::Improved for the syntax parsing rather than trying to do it myself (in perl, no less). Hairball doesn't begin to describe perl's syntax. In any event, what is done is done. And, for better or for worse, it is now open sourced for others to use or improve:
The whole ordeal really drove home the importance of simple syntax in language design. Maybe one of these days I'll get a chance to write up my experiences with perl's implementation from when I was writing a library to simplify embedding perl in C programs (hint: perlembed doesn't even begin to cut it). The lesson I walked away from with that exercise was that the face a language presents to the world, i.e. its syntax, can tell you a lot about what its implementation looks like. And I don't want to go there again.