CantRemembrances

Oh, there is such joy in the process of upgrading to Mac OS/X Snow Leopard for us developer folks. Me, I chose the in-place ugrade path … my co-worker, who chose the from-scratch path, was deprived of some of these pleasures. Then again, he had to reconstruct everything from scrach, so he had his own barrel of monkeys to contend with.

Here’s all the bumps I ran into, pretty much in reverse order as I tried (unsuccessfully) to do the minimum amount of work possible :) I had to go pretty much this entire process twice — once on my work Macbook Pro, once on my identical home verison — so I figured I might as well document all of this crap down in the hope that it may reduce the shock and awe of future migrators. Of course you may run into a mess of fun issues not described here … And pardon me if the instructions aren’t perfect, because I’ve tried to boil a lot of this down to the it-finally-worked steps extracted from the frenzied back-and-forth of my real-time upgrade experience :)

Backups

Yes, this is just common-sense developer stuff (as is a number of the other obvious things that I call out in this post).

You’ll probably want to do a full mysqldump before upgrading. You can dump your port install and gem list --local listings up front as well, or wait ’til you get to those respective steps below.

MacPorts

If you also chose the MacPorts library system, you’ll need to re-install it from scratch. You’ll need X11 from the Snow Leopard from the OS/X install disks, and download the latest version of Xcode. Follow the migration steps as outlined on their Wiki; it does the trick.

Save off your port install list as a reference. Now, your MacPorts install will be completely toast, so that command won’t work until you re-install. No problem though — all of your packages will still be listed even after you upgrade.

The port clean step in the Wiki will crap out in the http* range, but that’s fine … you can probably skip that step anyway. Re-install your core packages and you’re good to go. I suggest installing readline if you haven’t, because it’s very useful in irb or any Ruby console.

MySQL

It was not necesary for me to build MySQL from source. Instead, I just installed the x86_64 version of MySQL — the latest was mysql-5.1.42-osx10.6-x86_64.dmg af the time of this writing.

If this is a 5.x verison upgrade for you as well, the install will just re-symlink /usr/local/mysql, so your old data will still be in your previous install dir. I had mixed results with the InnoDB engine when just blindly bringing the data/ over into the new install, so you may need to re-build your schemae from your pre-install SQL dumps.

As per usual, you’ll probably need to whack your /var/log/mysql/*binary* files in order to get past mysqld startup errors.

x86_64 ARCHFLAGS

Snow Leopard is a lot more native 64-bit than previous OS/X versions, and when you do your manual builds & makes, you may want to set the following environment variable:

export ARCHFLAGS="-Os -arch x86_64 -fno-common"

You’ll see a set of similar (though mixed) recommendations in the blogs I reference below; this particular flagset worked for me.

Ruby

I built Ruby 1.9 at work, and 1.8.7 on my personal machine. Either path is fine, just pick up the latest source of your choosing. Chris Cruft’s blog post goes into some of the details I’m describing here as well. Basically, the README boils down to:

autoconf
./configure --with-readline-dir=/usr/local
make clean && make
make install

Though there’s no reason in the world that you’d want to — it has been superceded — do not install ruby 1.9.1p243. If you do, you’ll never get the mysql gem to work. Or wait, or was it mongrel? Well, it was one or the other … just trust me, it’s bad.

Gem

I re-built gem from source from scratch as well, just to be sure. Save off your gem env and gem list --local as a reference. And before you start installing gems, you’ll also probably want to make sure you’re fully up-to-date with gem update --system, though that’s probably redundant.

Uninstall and re-install all of your gems; if some won’t uninstall even though they’re listed, it may be an ins