* What problems have people found with Cygwin Perl?

I've been using Cygwin Perl for several months and the only problem that springs to mind is that occasionally when I'm makeing a module Win98 locks up for a few seconds (which subsequently convinces my modem it's no longer connected throwing me off the net).

* How fast is Cygwin Perl compared with AS Perl?

I've not noticed any appreciable difference, but I haven't been running in time critical or large-scale applications with it either, so I couldn't say with any certainty.

* How much of CPAN works okay?

I'd say around 95% works a charm, and the other 5% is just a little fiddly. The only problems I've had are with the XML::Parser suite, but that's mainly because I couldn't setup up expat properly, so nothing to worry about there either.

* For people who have used both, which do you prefer, and why?

I definitely prefer Cygwin. Why? CPAN CPAN CPAN. I'd always had 'issues' with CPAN on AS, but it couldn't be easier on Cygwin (well maybe if you were using CPANPLUS ;-) Although AS does have a really nice setup and it's got lots of pretty HTML docs, so it's nicer from a users view.

* What functionality does AS Perl have that Cygwin Perl does not?

It integrates with Windows very nicely with it's filetype associations, PerlScript, comprehensive docs and other various niceties. I'd say if you want to develop perl apps for Windows then AS will definitely be the easier route of the two.
HTH

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broquaint