Beware the Leopard OS X Upgrade

Nov 5th, 07 | 12 remarks

Yesterday morning, after over a year of anticipation, I gleefully started the task of setting up my very first Mac, a beautiful 24″ iMac. Since then I’ve been getting to know my new machine, installing software, transferring data, and just generally enjoying the speed and simplicity of it.

Then, this afternoon, I decided it was time to upgrade to Leopard via the DVD which came in the box.

Unfortunately, what I didn’t know DID hurt me. I had already allowed several updates to Tiger, and apparently one of them (iMac Software Update 1.2 Tiger) has wrecked havoc with regard to admin privileges. Something about the update conflicts with the upgrade, and will prevent you from logging in after installing Leopard.

Nice huh? Especially for a first-timer who barely knows the system to start with. Shame on Apple for not thoroughly testing the updates with their latest OS!

Anyway, this article explains how the length of your password may be the problem. I followed the steps on how to change it at the command line verbatim, but it didn’t work. Then I tried a suggestion I found in the Apple forums for logging in under Safe Mode as a single user, and rebooting from there. That was useless as well.

Finally, I discovered this long, but very good thread which goes into detail about reinstalling with an Archive and Install option. Specific instructions can also be found here.

As I write, the (re)installation process is almost complete. I’m crossing my fingers. I’m also hoping that by posting this entry I can spare someone else the frustration and total distress I’ve been feeling over the past few hours. If you’re considering an upgrade to Leopard, be careful about the updates to Tiger that you’ve installed! You might be in for more than you bargained for.

More Resources:

Update: Thankfully, the Archive/Install option worked. If you run into the same trouble I had, I recommend this work-around. It sucks to spend another hour or so reinstalling, but all your data and settings will be preserved and from what I can tell so far - Leopard is totally worth it. :)


  1. Kevin S.

    Well, that’s a bit of bad luck. I had a perfect upgrade from Tiger to Leopard. About reinstalling the apps, I don’t think it’s such of a big problem, since you mainly only have to drag and drop the icons into de Applications folder. If you’ve done the Archive and Install upgrade, you should have all of your previous apps on a Previous System folder.

    Anyway, all I can say is enjoy the new cat, it’s got some awesome new features.

    Btw, you should check these two apps out. Personal recomendation. :)

    http://macrabbit.com/cssedit/
    http://www.pixelmator.com/


  2. Charity

    Thanks for the links Kevin. The Archive install worked like a charm so I didn’t have to reinstall any software or worry about losing any data that I had already migrated over from my PC - whew. I wonder if I need to find the Previous System folder and delete that now? Gonna have to read up on that.

    Leo is slick indeed. I love it already. I’m also impressed with how much more simplified Mac is compared to Windows (especially when troubleshooting). Everything is drag-n-drop easy. Don’t know if I’ll be a convert for life, but I see what all the fuss is about now! :)


  3. Dan Anton

    That sounds like a nightmare…getting your brand new machine hooked up and upgraded only to find out it’s messing up due to other upgrades; glad you trouble shooted and solved it on your own. I had a firefox problem once and the only way to fix it was to delete a profile and create a new one


  4. Aaron :: miLienzo.com

    She’s a convert!! :D

    Well done, you wont look back now (despite these initial troubles you’re having). I’m getting a new mac this month too which I’m quite excited about.


  5. LaurenMarie - Creative Curio

    That’s why I stick with Windows ;)


  6. Charity

    Which Mac are you getting Aaron, have you decided yet? Even with the hiccups I’m really pleased with everything so far - the OS of course AND the hardware. The new keyboards alone are a fine example of Apple’s ingenuity, and I just can’t get over the display. Gorgeous. :)

    I still have a lot of questions and much to learn but I don’t regret my choice for a moment!

    @Lauren - It’s a little scary transitioning, but oh boy you’re missing some very cool features that Windows doesn’t hold a candle to! I’ll admit there are some things I’ll miss about Windows though. Even Firefox on Mac seems a little buggy. I’m keeping my laptop (PC) around “just in case”. I guess at this point you could say I’m a hybrid geek. ;)

    I have a friend who keeps teasing that I’ll “come home to Windows” sooner or later… but the more I get to know Mac, I’m not so sure!


  7. LaurenMarie - Creative Curio

    I’ve used Macs before and the way they operate just drives me up the wall! I’m much more savvy with Windows and I have to be able to customize the way I want.


  8. Char

    Welcome to the Mac side. Actually, I have both a PC and an iMac - love them both, use them both. The new header on my personal site (CK) was made on the Mac and the type was placed in on the PC. Don’t ask - it just works well that way.

    I have not upgraded my Mac to Leopard yet - maybe this weekend…


  9. Charity

    @Lauren - I agree there seems to be more customizability (is that a word?) in Windows - at least based on my limited knowledge of Mac so far. I’m a little disappointed with the Dock’s lack of features for example. I assumed it would be like ObjectDock for Windows but no such luck.

    @Char - thanks! Is the Mac side anything like the dark side? ;) I ordered CS3 today and remembered our conversation on qualifying for the upgrade price when switching platforms. Thanks for the advice! A phone call to Adobe made it fairly painless. Looking forward to playing around with Fireworks now that I’ll have it for the first time. I might have to bug you for some tips once in a while.


  10. Aaron :: miLienzo.com

    I’m actually going to get a Mac Pro. Not because I’m filthy rich, but because the upgradability means it will last me twice as long as a PC or iMac (I buy a new computer pretty regularly).

    I’m saving a few bucks by getting an education discount and buying a dell monitor rather than the Apple monitor…

    And I can’t wait till I get it :D !


  11. Tara

    What a nightmare - I am in the same position just bought a new imac too loaded with tiger but a free DVD with leopard. Do you know if there’s any way to check if your Mac has already had the upgrade? Or maybe I’ll just stick with Tiger for a bit?


  12. Charity

    Hey Tara I guess we’re all on the same wavelength. I think if you go to System Prefs > Software updates, it’ll scan then list every update available. You see the Tiger update listed just deselect. If it’s not, chances are you already have it. I’m not sure how to check for sure. Sorry I’m not more helpful.

    I think you might be okay at this point though. I think Apple has patched everything. Let us know how it goes for you and good luck! :)

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