OS X Tiger upgrade: The ugly

analysis
May 9, 20057 mins

I'll be all over the subjective and analytical coverage of OS X Tiger in InfoWorld's print reviews, my Ahead of the Curve column and this blog. I think Tiger is just grand, and I'm way past the "Apple can't suck" stage of my working relationship with the Mac. But as much as I admire this OS, putting myself in the shoes of what I considered to be a relatively new user--one who came to the platform late in OS X 10

I’ll be all over the subjective and analytical coverage of OS X Tiger in InfoWorld’s print reviews, my Ahead of the Curve column and this blog. I think Tiger is just grand, and I’m way past the “Apple can’t suck” stage of my working relationship with the Mac. But as much as I admire this OS, putting myself in the shoes of what I considered to be a relatively new user–one who came to the platform late in OS X 10.2’s life or during 10.3’s–left me thinking that this isn’t an upgrade I’d recommend to a non-experienced user.

I can now count myself among the ranks of experienced users. Since OS X 10.3, I haven’t found the need to subject OS X to the “wait for the first service pack” rule. I’ve been working with seed releases of Tiger for a year, but not on production hardware. The true test was an upgrade to Tiger from OS X 10.3.9 on my 1.5 GHz 17-inch PowerBook G4. That machine is to my professional life what Diet Pepsi and trail mix are to the rest of my existence.

The upgrade was a frustrating, time-sucking exercise from the start. It failed partway through, complaining that it could not write a particular file. There was no reason for this. The hard drive passed two sector-by-sector validations as did the install DVD. The install partition showed clean on fsck (file system check, the Unix utility fronted by the Disk Utility GUI with the Verify and Repair buttons) and on Fix Permissions. Even deleting the existing file and making its parent directories world-writable didn’t work.

Those familiar with OS X upgrades know that the installer can’t handle an upgrade that failed in process. I pushed ahead as though I didn’t know I couldn’t continue. If I were pretending to be a Windows newcomer instead of a Mac newcomer, I’d discover that I can pull the plug on a Windows system at virtually any point during an install or upgrade and have it recover without loss of the system’s original data. This raises a question about the ease-of-use advantage that Apple claims over Microsoft. I’ve long thought that for a substantial percentage of users, Macs’ ease of use paradigm extends only to systems used as shipped or managed by experts.

With Tiger on the PowerBook, the failed upgrade-in-place meant that I was screwed. That state remained for a solid three days.

My initial upgrade attempt required the use of a LaCie external FireWire DVD drive. My PowerBook’s internal SuperDrive cratered just before the install. I had another external drive, an LG DVD+/-/RAM device (a sweetheart of a drive–see a follow-up post), that I installed in a Belkin USB 2.0 external chassis. The combo gets along famously with my Power Mac G5, Xserve G5 and every PC box in my shop.

When I attempted to boot the 17-inch PowerBook from the LG drive, the drive spun up promisingly but the PowerBook booted (rather, failed to boot) from the busted hard drive image. My first cheat was to try activating the Mac’s boot media list by holding down the option key at power-up. It did not see the OS X install DVD at all.

It rang a distant bell that PowerBook couldn’t boot from USB. The junkiest PC in my pile boots USB. I’m writing this on the third generation of PowerBook that’s run through my lab. It hadn’t occured to me that a late-model PowerBook would not boot from a USB optical drive.

I ended up putting the 17-inch PowerBook in target disk mode, which for the uniniated is a nifty, life-saving hack that turns a Mac system into an external FireWire hard drive. I installed to the 17-inch 1.5 GHz notebook machine from an 867 MHz 12-inch PowerBook. It took a while. It’s a lucky thing I had another Mac. If the 17-inch PowerBook had been my only machine, I’d have been up the creek. Of course I had backups, but making this work in-place was a requirement of the exercise.

Running the 17-inch PowerBook in target disk mode did get OS X through the upgrade process to its be right back reboot. I felt relieved and called it a very late night.

Success required not only using target disk mode, but switching from an in-place upgrade to archive-and-install, the latter being a method that moves existing system files to a safe directory before clobbering them with the new OS. This trick is helpful for those of us who speak Unix, but who else would know what to do with those backed up files? There’s no opportunity to back out the upgrade, boot from the safe copy of the system files or pull in portions of those files to fill gaps in the new installation (e.g, an app that’s missing its run-time preferences).

I woke the next day ready to celebrate my victory, but the 17-inch PowerBook would not boot. The screen cleared to the GUI progress bar and sat there. Booting into verbose mode, which reveals the hidden boot-time text that might remind mere mortals that they’re running Unix, showed that it was a miracle the machine got to the GUI at all. Almost nothing loaded as the OS expected it to, and that which did load didn’t initialize and died at launch.

I still refused to punt; I had to play like that wasn’t an option. I booted to single-user mode and dug through the logs as a programmer digs through build errors. Whee. It amounted to shutting off all OS X network services, fiddling with the config settings of each and test-launching them from the command line to see how far they’d get.

It still wouldn’t finish booting. The Big Fix at the end was a hunch that the Netinfo database, the unacknowledged center of every Mac’s universe, was scragged. Woebetide those with a busted Netinfo. I first tried to rebuild NetInfo from a backup copy. That process is infamous for taking several hours to complete with no feedback on its progress. I gave it 24 hours and decided that I could have re-entered the entire database from scratch typing with my feet by then. I torched the database and built an empty one. At the next boot, success. Only I couldn’t log in.

Blowing the Netinfo database away removed the users I had added to the system. It was a tiny matter of copying another user record as a template and filling in my old accounts’ names and IDs.

After that, the system booted effortlessly. I haven’t reset it or allowed it to power down for five days, and I get no boot-time warnings. Total time invested/lost: Four business days.

If I had been an OS X GUI user (especially a Windows switcher) with the faith in the OS X upgrade process that I had in Windows’, I couldn’t have done this without an expert’s help. Attempting to proceed using the scant advice Apple offers would have led me to blow away my existing data and applications. If I had called Apple with this, telling them that a clean install wasn’t acceptable–perhaps I had preferences that took me forever to pull together, or apps for which I had misplaced the installation media (the latter true in my case)–I wonder how AppleCare would have walked me through this after the initial upgrade attempt failed. I’m going to wild-guess that I’d have gotten the same reformat, reboot and reinstall advice that HP or Dell would have dispensed.

I have never had the least hiccup in any OS X Tiger clean install since the first preview was released at the 2004 Worldwide Developers Conference.

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