Undeterred, I went to grab the source and compile it myself. It didn’t work. Eventually I figured there were two key issues:

1. FreeImage’s source was prepared for Mac OS X 10.3 (Panther)
2. FreeImage was trying to compile for i386 (32-bit) and my Ruby install is x86-64 (64-bit)

First problem is easy to fix, just replace both instances of /Developer/SDKs/MacOSX10.3.9.sdk with /Developer/SDKs/MacOSX10.6.sdk (or, 10.5 for Leopard, or 10.4u for Tiger).

The second part was a bit more fiddly because I wasn’t sure if order was important, so I started by replacing all instances of i386 and I386 with x86_64 and X86_64 respectively. Then, I replaced all instances of ppc and PPC with i386 and I386.

If you don’t want to worry about making all these changes, you can simply download my Makefile.osx here. It’s built for Snow Leopard, but it’s easy to change it for Leopard or Tiger.

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Catching error: 'Can\'t call method "value" on an undefined value at /System/Library/Perl/5.10.0/darwin-thread-multi-2level/IO/Uncompress/RawInflate.pm line 64.
' at /System/Library/Perl/5.10.0/CPAN.pm line 281
CPAN::shell() called at /usr/bin/cpan5.10.0 line 199

Not good. So, how to fix it? Move the broken IO::Uncompress module out of the way. In a terminal window, copy and paste the following

sudo mv /System/Library/Perl/5.10.0/darwin-thread-multi-2level/IO/Uncompress/RawInflate.pm /System/Library/Perl/5.10.0/darwin-thread-multi-2level/IO/Uncompress/RawInflate.pm-broken

Once that’s been shifted out the way, it should work provided CPAN was configured with the proper paths to your tar, bzip2 and gzip executables (if not, nuke your /System/Library/Perl/5.10.0/CPAN/Config.pm and start over).

Note: This isn’t a long-term solution, some things like CPAN::SQLite won’t install if IO::Uncompress::RawInflate is missing, but at least it gets some functionality back into CPAN. I’m very interested in hearing of any better fixes for this.

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