Ugh. The sqlite that ships with OS X doesn't have the full text search module enabled. This isn't usually a problem: just install a custom version, e.g., via macports, and then (re)install the sqlite3 gem. Works great for 1.8/1.9. Fails miserably for macruby. I think the problem is that while macruby doesn't link to any sqlite, CFNetwork does, and it links against the the system version. That link gets resolved before the gem extension is loaded, so the system version is used. I don't have much experience with dylibs on OS X, so I'm not sure if there's a good workaround for this. I can hack a workaround by actually calling out sqlite3 on the macruby link line and telling it to look at the maports version. That gets loaded before the framework stuff and everything seems happy. But, it's gross, of course. Ugh.