Because windows 2003 is a 32bit system
I am far from an expert on this topic, but my understanding (admittedly, just from Wikipedia) is that there is a 64-bit edition as well. If you have experience with Windows Server 2003, can you say if a 64-bit Perl wouldn't work on a 64-bit edition?
Don't use the latest perl, consider 5.20 or 5.22
Why?
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Thanks for the info. It looks like some older versions of GD indeed did have some trouble, at least with their tests. matro made a good point too: Strawberry Perl ships with GD, as far back as 5.8.9.4, with GD 2.44.
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