This is what I do when I’m not at work.

Tragistrophic Leopard Upgrade

Posted: January 19th, 2008 | Author: | Filed under: computers, grousing, sorrow | 4 Comments »


The advertisement from Apple says “So advanced, it practically installs itself.What a load of garbage! Here is the story of my nightmarish upgrade to Mac OS X 10.5 (Leopard).

Before we even begin, I have to own up to my culpability for not ensuring I had full and complete system backups before beginning the software upgrade. In my defense, I did not have sufficient external disk drive space to perform this backup, otherwise I would have done so. And while I have seen glitches and issues with Apple upgrades in the past, I have never experienced complete, total, catastrophic data loss. Now I know what true suffering feels like…

The new Mac OS X release “Leopard” came out while I was accepting a new job and moving across the country, thus it wasn’t a good time to perform an operating system upgrade. So I waited. It wasn’t until I had settled into my new town and was learning the ropes at my new job that I felt the urge to see what all the fuss was about. November 12th was that fateful day. A day that will live in infamy as far as I’m concerned. I had three years of customizations and perfected settings in my 10.4 Tiger system and was concerned about losing those settings. I should have been a lot more concerned.

I have been having data storage problems lately, as my music library grows well over 300 Gigabytes in size and my movie collection is easily 100 Gigabytes or more. Currently I cannot afford to purchase more external disk drives and the idea of burning everything onto DVDs is about as appealing as unnecessary root canals. I had as much as possible copied onto my external hard drive, but there was not enough free space to make a current copy of my user directory or the all important ~/Library directory (hint: your email lives here if you use Like I stated above, I’d seen some funky behavior at upgrade time in the past, but never had everything destroyed.

My main system drive is 500 GB, which in real terms means 465 GB. At the time, I was using 460 GB on this disk. The first Leopard upgrade attempt failed because there was not enough disk space to install the new operating system. So I grudgingly deleted a few crappy movies and other random files of lesser importance. Once I had about 7 GB of free space, I chose the most minimalist upgrade option and the installer told me it would need just under 5 GB of disk space. I figured “No problem! I’ve got at least 2 GB to spare.” This was where my thinking was terribly, terribly wrong.

On a fast system, the average time to upgrade an OS is about 20-25 minutes. Mac OS X likes to perform a system analysis before actually beginning the upgrade and this can run a couple of minutes tops. Well, it was stuck in an “Analyzing system” state for a good hour or so before even beginning the install process. This was my first clue that something was going awry. I assume it was indexing all the files on my hard drive during that time, but it should have stopped itself at some point with a message akin to “Dude, your hard drive is too full. This upgrade is going to make your data toast.” Instead, it ran the disk through a grinder for hours and hours — always telling me that it was 99% installed and “1 minute from finishing installation.”

After four or five hours of waiting and praying that this wasn’t the end of my happiness, I called my friend Ian in a panic. It was the middle of the night where he was, but I had an emergency! He nervously tried to offer trouble shooting advice from thousands of miles away and we finally conceded that my only option was to power the box down and pray for the best. Well, the power up was a bit shaky with screen resolution doing some crazy things and it seemed like it took 10 minutes to boot (but was probably closer to 5 minutes). Behold! A login prompt!!

From the first moment I logged in, the machine was exhibiting bizarre behavior. Lots of GUI errors and things jiggling and fritzing with no correlation to user input. My data was still there, however, and I was now running a Leopard system. But the instability bugged me and I wondered if there was an Apple patch to deal with issues on freshly installed systems. I don’t remember checking available disk space, but if I had to guess, the main drive only had a couple of MB left free. Foolishly, I went to Software Update and commanded it to heal thyself. This was a bad idea.

Had I known what lie ahead, I would have gone immediately to the all-night external disk drive store and purchased an emergency drive (you can always return it in the morning, right?). So, the PowerMac hurled and wheezed and spun its wheels for hours downloading Apple patches and filling up the remainder of space on my drive. Then it wouldn’t boot. At all. Like nothing. Nada. Blue screen of “You’re a dumbass.” And with that, all my years of diligently acquired data were gone. I spent more hours into the wee morning trying to access it, perhaps boot it as a firewire target drive, anything. All to no avail. My Mac was gone. I was making the sad Mac face. Well, it was more like the completely exhausted and utterly pissed Mac face. I had to go to work in, like, three hours.

The next day I sat at work completely disgusted with myself. I ran over every data recovery scenario in my head and thought of my mistakes along the way. As you can see, I am taking most of the blame for this royal screw-up, but I still refute Apple’s claim that Leopard is “So easy to install, a monkey could do it.” It told me that it needed 5 GB of disk space. I had 7 GB of available disk space. At no point did it say, “Oh yeah, we was just kidding about the 5 GB claim. ABORT! ABORT!!” That error message would have been a welcome sight compared to losing all my files.

So here is the post mortem: I lost ten years of meticulously archived and sorted email. TEN YEARS! A folder for each friend, family member, business contact, you name it. All gone. This has burned my britches the most. I am sad that there are people I will probably never hear from again and I have no real way to contact them without an email address. I lost every single imaginable system preference, saved password, application customization — basically anything that helped me work better, harder, faster, stronger. I lost every single file I had added in the month prior to November 12th. That was hundreds of MP3 files, quite a few movies, lots of personal photographs, and many text files with notes about important shit that I have now forgotten. The frustration, at times, has been too much to bear. Oh, and I also lost all my applications — the things that enabled me to make websites and edit photos and record music and do just about anything. All gone.

November 2007 was one of the saddest months of my life because of this data loss. All thanks to a wonky OS installer that told LIES! Lesson learned: NEVER TRUST AN APPLE UPGRADE! Now I don’t want to have any data on my machine at all. I am looking for a network file server solution to house all my important data and I’ll just keep current working projects on my workstation — with regular backups, of course. I don’t know what is embarrassing in other lines of work, but when you are paid to do computer work and you completely hose your home system it is more than egg on your face. It is like a Denver omelette with jalapenos and motor oil all over your face. I felt like I had been Jackassed and Punk’d and Flip This House’d all into one. Total Lame-Tard status.

Anyway, in case you’ve been wondering what I’ve been doing with myself over the past few months, I can tell you I’ve been working a lot. And in the few hours I’m not eating, sleeping or working, I am tiring endlessly to restore my system to the state it was in before November 12th. I am now living in a post-11/12 world and it is painful and terrifying. Never forget November 12, 2007. The day I lost my data and all related happiness. That is my tale of the tragistrophic Leopard upgrade. I hope it didn’t happen to you!

As a final note, I want to plug Joe Kissell and his amazing work on the Take Control series of eBooks for Macintosh. This guy is awesome and historically I have purchased every version of his “Upgrade to [new OS X version]” eBook ever published. This time I was in a hurry and look what happened. I should have bought his eBook, read its contents, meditated on the Kissell koans and then hired a shaman to do my upgrade. If you try to tell me there is a better person out there writing about Mac upgrades, then I will beat your ass. Capiche?

4 Comments on “Tragistrophic Leopard Upgrade”

  1. 1 KJ said at 8:18 am on January 20th, 2008:

    By failing to back up your home data, you are doing what every geek in the world does! I know it’s only a matter of time before my July 2006 backup is out of date…

    I am sorry for your loss.

  2. 2 Amanda said at 2:25 pm on January 20th, 2008:

    I can’t even imagine… I wish I had the money to get a drive to back up my photos, because I would LOSE. MY. SHIT. if I lost them all. I really should just get Alan to give me some space on his external hard drive.

    I’m really sorry, dude… on the one hand, you did make some mistakes, but it really shouldn’t have been that catastrophic of an experience. You would think (hope?) that there would be some kind of warning when an install is going to completely fuck your shit up. Sad.

  3. 3 suki said at 9:43 am on February 19th, 2008:

    I am so, so sorry that you lost all that stuff – but man, you sure can make a tragistropic event EFFING FUNNY.


  4. 4 Eric Heitzman said at 7:07 am on March 14th, 2008:

    I got bit by this one too, but I found a solution.

    The problem comes from a poorly written Logitech driver that in turn installs a program called the Application Enhancer (aka APE) into the System folder. APE works fine in Tiger, but not in Leopard, hence the blue screen.

    Fortunately, there are several fixes and you don’t have to lose any of your data!

    Here is the solution I used to fix the problem:
    (1) Start up in single-user mode by holding Command-S after restarting the computer. Note that single-user mode always uses the US English keyboard layout.

    (2) Type these commands, each on a single line followed by Return:

    /sbin/fsck -fy
    /sbin/mount -uw /
    rm -rf /System/Library/SystemConfiguration/ApplicationEnhancer.bundle

    Check out these resources for more information on the subject:
    Apple Knowledge Base Article 306857
    Mac OS X 10.5: “Blue screen” appears after installing Leopard and restarting

    Daring Fireball’s (John Gruber’s) post on the subject, which is how I found the Apple KB article in the first place:

    I notice your post is dated 1/19/2008 and the Apple KB is dated 11/08/2007. I hope you haven’t reformated that computer…

    Good luck everyone!


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