I’ve Been Attacked by a Leopard

14 Nov ’07

It’s now been about 2 weeks since I installed Apple’s Leopard on my two Macs, and without a doubt this upgrade is the worst OS upgrade experience I’ve ever had. I think that’s saying something – I survived Windows 98, however many iterations of XP there were, and fled to the Mac in part because I was tired of spending so much time on forums and technical support pages trying to get my systems to work as advertised.

Well, I’m back on the forums. From start to finish, this experience with Leopard has been a complete nightmare, and I’ve needed a lot of research and help to get me through it (conservatively, I’ll estimate about 100 hours of time spent trying to fix things so far) – and it’s still not over; there are still several issues I’m trying to resolve. I’m sticking with the Macs, but my trust in Apple has been beaten soundly about the head and shoulders, and I’m going to be a lot more careful about early-adopting Apple products in the future. Comments are open, so go ahead and say I told you so. But first, walk in my footsteps for a little while as I set the scene.

Step 1 – enthusiastically open the Leopard box and insert DVD into Mac #1, a MacBook Pro. First mistake: even though I have a full backup, it’s a couple of days old. But I don’t freshen it up, because nothing ever really goes wrong with a Mac, right? Not so much. The install screen that asks where I want to install Leopard says I have no hard drives. This will come as a considerable surprise to my Mac. I reboot and retry – a few times – with the same result. The forums report that this is a common problem and a number of fixes are suggested. I go through several of them and after about 3 hours I find one that works.

Step 2 – based on advice from a number of sources, I install using the “Archive and Install” feature – this does a fresh install but saves all your apps and files to a folder so you can add back in whatever you want to keep in the new system. Except that after the several hours it takes to install, I’m presented with a screen telling me that the install failed. I reboot, and my files – everything – have disappeared. Leopard, however, is on my Mac. I think it’s laughing at me. It’s going to be a long night.

Step 3 – I spend several hours looking for my files. I notice that there are about 50 gigs of disk space unaccounted for, so I go online looking for info about hidden files. I find a terminal command to reveal them, and after digging down through many layers of directories I find my files – most of them, anyway. Between the files I’ve just found and my backup, I’m up and running after about 5 hours of work. I reboot to get a fresh start, and when the Mac restarts there is a question mark on the screen. I’ve heard about this question mark – it means the rest of my day is shot, because the Mac can’t find an OS to startup from. Yes, my Mac is definitely laughing at me.

Step 4 – I reinstall Leopard, this time choosing a simple upgrade. How one can upgrade an OS that isn’t there, I don’t know, but the Mac seems unaware of this inconsistency. After several more hours, the upgrade is complete, and I’m back to where I was at the end of Step 3.

Step 5 – my keychain is gone, so I start rebuilding it. I can’t access email, because my account info was on the keychain and in an encrypted passwords file. I contact the vendor of the encryption app, 1Password, from a web form on their site, and with their (very excellent) help I restore my backup. From one task to the other, I spend several more hours getting up and running.

Step 6 – I try to get a video chat with iChat AV going with a friend. It worked fine on Tiger, and we’ve both upgraded to Leopard. It won’t work. I venture online and find many posts from people with the same problem. Different solutions are offered, from tinkering with port forwarding on the router to banging your head against the wall and screaming. None of it works for me.

Step 7 – Now that I’m back up and running, I spend some time cleaning up old backups and the like on an outboard 320G USB drive I use. I built the drive myself with a simple enclosure and a nice Western Digital drive and it’s been an Old Faithful for me. I move all of the files off of it so I can partition the drive with Apple’s Disk Utility. The partition fails, and I get an alert telling me that there’s been a disk input/output error. I try it again, and again and again. I try everything. Same result. Again, I go online. I don’t find much (perhaps because the disk worked until I tried to erase and partition it, something people would generally do only rarely), but after some digging I find a few posts that suggest that Leopard may not work properly with some USB controller chips. I haven’t wanted to know anything about USB controller chips since 2004, so I spend some more time banging my head against the wall. Later, after the crying, I find a post that suggests that the drive can be restored using Western Digital’s disk utility, on a Windows machine, if the partition is formatted with FAT32. I try it, and it works. I try reformatting it on the Mac, and the disk fails. I don’t want FAT32 partitions, so the disk goes on the shelf until Apple issues a fix. I order a new drive – LaCie is having a big sale on eCost, and 500G-1TB drives are pretty affordable. I order the firewire 400 drive. Nervously I look at my other main outboard drive. Is it laughing at me? I start backing files up to DVD.

Step 8 – One of the things I couldn’t properly recover is my iTunes library – I have the music, and I have the library file, but for some reason iTunes can’t figure out where the music is. I’ve checked all my settings 18 ways to Sunday, and can’t figure this one out. That’s 100 gigs of music, laboriously tagged and starred and playlisted over about 18 months and sync’d to various iPods. Poof. Again, with the head-banging.

Step 9 – I try to add music to iTunes. Again, an error message. This time, I don’t have permission to access my Music folder or a file in it. I’m the admin on this computer, so that makes no sense. I check permissions, then repair them. No change. I can’t add new music to iTunes. This time I don’t even bother to go online. I’ll just wait a few days and see whether anything changes. Of course it won’t – but I need a break.

At some point, I suppose there will be a Step 10, 11 and so on. And there will probably be an OX 10.5.1 etc before too long as well. But whatever happens, this experience has soured me. I spent 20 years managing multiple machines through several iterations of MS operating systems and this is the single worst upgrade experience I’ve ever had. And it’s not over. I’m still a convert, but much less happily, and certainly much less credulously, so.

Update: Fake Steve Jobs is not impressed.

Updater: To its credit, Apple has released the rumoured update. It did this because, if you’ve read the comments to this post, I broke Leopard.

Updaterer: I wonder if I broke Scoble’s Mac, too.

Updaterest: Scoble unloads and gets hit with a busload of clueless commenters.

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