Snow leopard upgrade woes

So on a whim last weekend i decided upgrading my new Macbook Pro to snow leopard on Day 0 would be a good idea. The upgrade went flawlessly--that is, until I actually tried to use my development environment afterwards.

The root cause of all the trouble was that in SN, unlike Leopard, most applications are 64-bit, which means your Ruby libs that have C code behind the scenes need to recompile. But the default compile only compiles them linking to 32-bit code. In a lot of cases this doesn't seem to matter; the big one people run into is mysql (see this post for details on how to fix it).

Another one it took me awhile to find though, was ruby-debug. When my development partner and I were trying to debug a particularly hairy problem this week, my machine refused to drop into the debugger. It took me awhile to realize what the problem was, and running this fixed it:

sudo env ARCHFLAGS="-arch x86_64" gem install ruby-debug

Once I ran that, everything was golden again.

More adventures to come...