The Harrowing Journey From Tiger to Snow Leopard

Unlike most Apple users, I didn’t make the quick jump from Tiger (10.4) to Leopard (10.5).  Mostly because I’ve learned the hard way not to be the first in line for upgrades.  And when I read about the changes they were making, I thought “I’ll wait until they work out the kinks.” And then they announced Snow Leopard (10.6)  and touted the $24 upgrade but, if you looked close at it, that was only from Leopard to Snow Leopard, where little was changed on the service (but much under the hood was redone).  A little looking and I found that I had to get the Mac Box Set with 10.6, iWork, and the new iLife, which I wanted anyway.  And lots of my tools that wanted to use only worked with Leopard on up anyway.  So Snow Leopard it is.

I ordered my Box Set and waited for Amazon to ship it (it was $20 cheaper there and no taxes. Yes, I’m that cheap!).  When I got it in my hands, and got ready for the upgrade . . . I did a backup first.  SuperDuper is my friend.  Before this process was over, it became my lifesaver.

So I stuck the Snow Leopard disc in, and told it that I wanted to upgrade.  The machine rebooted, the Snow Leopard install came up, and said it was starting and then . . . it quit, telling me that there was not enough room left on the drive.  Which was very possible — there was a lot of junk on that drive.  So I took the disk out and rebooted, thinking I would remove some more junk and then do the upgrade.  And then it happened . . .

The machine wouldn’t boot.

My Mac would start up just fine, give me the Apple logo and then shut down.  I put the Snow Leopard disc back in and that didn’t boot either!   A little research showed my assumption about it booting from the DVD drive if it couldn’t boot anything else was wrong — instead it just stops.  You have to hold down “C” during the boot sequence to get it to boot from the DVD drive.  I went to find my Tiger install discs and booted with that.  I went to run the DiskUtility and did “Repair” but it said it couldn’t.   Arrgggghhhh.

I tried the DiskUtility with the Snow Leopard and it wouldn’t even Repair it — it was not a Snow Leopard hard disk!!  Arrggghhhh again!

Now I had a choice.  SuperDuper makes my USB hard drive bootable.  I could boot off of it but that doesn’t solve my problem — the boot info on the hard drive was messed up. If I booted from the USB drive and removed enough stuff to make Snow Leopard install.  But, still, nothing can repair my drive.  My data was safely backed up and I know that I didn’t need it all anyway and, with SuperDuper, I can go and copy the files that I wanted off of it anyway.  So I took a leap and erased the drive.

You read that right. I wiped the drive clean with the Snow Leopard installer and installed from scratch. Of course, the installer was more than willing to do that.

After that, things went mostly well.  I copied our Music and Preferences folders over and Safari, iTunes, and Mail all saw the changes and updated their databases.  The copying part took a while, but after that it was all smooth.

But I had lots of problems with MacPorts.  Emacs.app needs some manual guidence , Python2.4 has some weirdness, and PostgreSQL/PostGIS are always a pain to install.  But I got them going.

A clean install was a good thing — it got rid of the junk and I was able to move just the files that I needed.  And, thankfull,  SuperDuper demostrated that it’s worth 10x it’s $28 price tag.

So do your backup kids.