Watch out for little gotchas in the Lion upgrade

Watch out for little gotchas in the Lion upgrade

Summary: As operating system upgrades go, my move from OS X 10.6 (Snow Leopard) to 10.7 (Lion) has been remarkably smooth, with only a few minor glitches. I've got details, including what to do if you're confronted with a confusing Java dialog box and why Sonos owners should wait.


As operating system upgrades go, my move from OS X 10.6 (Snow Leopard) to 10.7 (Lion) has been remarkably smooth. I was up early enough this morning to sneak in ahead of the crowd, buy the $30 upgrade from the App Store, and have it installed before my second cup of coffee. Good thing, too—if I had waited a while I might have run into stalled downloads and connection errors.

There are already plenty of comprehensive reviews of Lion out there (the epic 19-page review by John Siracusa at Ars Technica is the heavyweight champion), so in this post I just want to make some observations about my experience that you might find useful.

See also:

The online upgrade worked very well, although the App Store interface is a bit confusing. I clicked the green Buy button at least four times without realizing that my purchase had gone through the first time. Eventually I clicked the Purchased tab, where a progress bar on the right showed me that the upgrade was indeed being downloaded. At 3.74 GB, the download took about an hour on a fast-but-not-that-fast Comcast connection.

I couldn’t find a Readme file or a Known Issues document for the Lion upgrade, only a generic support link. Normally that would be a dealbreaker, but in this case I decided to cross my fingers and press ahead in the hopes that there were no serious issues to watch out for. (One incompatibility I did earn about: If you own a Sonos device and your music collection is on a Mac, you might want to hold off on a Lion upgrade until a promised software update is available.)

Installation was quick. The progress dialog box estimated that the full process would take 32 minutes. After I kicked off the installer and blew past the license agreement, I went out to run some errands. When I came back to the office 40 minutes later, the logon screen was waiting for me.

I encountered three problems right out of the gate:

Windows Live Mesh for Mac stopped working. This is the software I use for syncing working files (documents and screenshots, mostly) between the different devices I use. (I used to use Dropbox but canceled my account a few weeks ago.) It had previously run trouble-free on Snow Leopard. Microsoft has confirmed that they're aware of this issue and are working on a fix. Update: Well, that was quick. A new, Lion-compatible build of Windows Live Mesh for Mac was released roughly 12 hours after Lion itself shipped. It should automatically update, or you can download directly here.

You might be prompted to install a Java runtime. This one had me stumped for a few minutes. I know Apple previously announced it was dropping Java support in this release, but there’s no indication of why Java was trying to run on my machine. The prompt is from Apple via Software Update. There’s no link to any support resources to explain whether this is safe and why it’s necessary.

It's worth noting that there's no "I don't want Java at all" button, only the option to install immediately or click Not Now to be nagged later.

Eventually, someone tipped me that the update is related to Adobe, and after a bit of digging I found a promising Known Issues document published by Adobe that included this subheading:

Java Runtime needs to be installed manually, otherwise applications may behave inconsistently

Mystery solved:

Since current Adobe installers and applications were built before these changes by Apple, our software anticipates that Java is installed. Adobe and Apple have worked together to ensure that you can install Java at OS install time, or optionally at a later time before you install Adobe applications. At runtime when you launch an Adobe application, you will be prompted to install Java if it is not already installed. If you do not install Java before running an Adobe application, there can be missing or improperly behaving features.


If the Java runtime is not installed, some issues that are known to occur include:

  • Failures to launch
  • Prompts to install Java runtime when attempting to use the applications
  • Applications may hang on quit.

Exchange AutoDiscover doesn’t appear to work properly in the new Mail app. My domain is set up with the correct AutoDiscover DNS records, and other clients have no trouble recognizing them. The new Mail app in Lion, however, unhelpfully demanded that I enter server names manually.

I might chalk this up as an anomaly were it not for a nearly identical report from a reliable source on Google+. This complaint on the MacRumors forum about a “buggy implementation” of Exchange Autodiscover in the Lion Gold Master release suggests we’re not alone. I’m looking more closely at this one.

I also found a glitch with the open-source Synergy utility I use to share a single keyboard and mouse between a Windows PC and my Mac. Previously, moving the mouse onto the Mac’s screen was enough to bring the screen back to life. Now I have to tap the Mac’s keyboard to wake up the display.

None of those issues are showstoppers. That’s good, because the benefits of Lion are relatively minor for my desktop Mac. I’m  using a conventional two-button mouse rather than a fancy Apple trackpad or Magic Mouse, so the new gesture support is unavailable to me. Being able, finally, to resize a window by dragging any side is long overdue.

One disappointment in the new Safari release? I confirmed that Apple hasn't reversed its horribly insecure decision to enable the "Open 'safe' files after downloading" setting. That setting has been abused by malware authors, for whom it makes social engineering all too easy.

I was relieved to discover that my Boot Camp installation of Windows 7 Enterprise worked just fine without needing any updates. Others weren't so lucky: Glen Murphy, who works at Google as design lead on the Google Chrome browser, reported via Twitter:

The OSX #Lion upgrade appears to have deleted my Windows bootcamp disk and all my data. I am sad.

Last month I upgraded this hardware significantly, boosting the RAM from 2 GB to 8 GB and swapping a fast 7200RPM Seagate Momentus hybrid drive for the pokey 5400RPM drive that came with the system. With those upgrades in place, I’ll be looking at virtualization solutions next.

Topics: Software Development, Apple, Enterprise Software, Hardware, Open Source

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  • RE: Watch out for little gotchas in the Lion upgrade

    Here is a pretty big gotch ya: everyone with a NAS backup will NOT be able to use Time Machine. No one. some type of protocol change in Lion. So, how does one access all those files the said to back up, eh?
    • RE: Watch out for little gotchas in the Lion upgrade

      If the drive is in the MyBookWorld line you'll need to wait for a firmware update from WD.
    • RE: Watch out for little gotchas in the Lion upgrade

      @scubarobert I am a fan of microsoft products and they are very user friendly and helpful if you know exactly how to use them.
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  • Ed, I'm sure you know about burning a restore DVD...

    Ed, I'm sure you know about burning a restore DVD from the .DMG file inside the installer package. This will be useful for installing on more than one Mac, on computers without a fast internet connection, or as a Clean Install on a new or reworked machine.
    • RE: Watch out for little gotchas in the Lion upgrade

      @olePigeon I dont know why do people have issues crating a backup of their data, in my openion backing up data actually keeps you on the safer side.
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  • Looks Like I will be waiting a little bit

    If I decide to upgrade my MacBook.. Of course I am trying to get work to replace it so that may come with Lion.
  • I have no use for Microsoft products

    So makes no difference to me.
    • RE: Watch out for little gotchas in the Lion upgrade

      @root12 -This was a review artcle about updating to Apple OS X Lion from Snow Leopard.<br><br>Other than a note that Mesh needed an update and one exists, an that the update to Lion didn't kill his Bootcamp, this has nothing to do with Microsoft products, so your comment is WAY off target.<br><br>Did you note that there was also an issue for Adobe's products (or anyone else's products) that use Java or do you just hate Microsoft and give everything else a free pass?
  • RE: Watch out for little gotchas in the Lion upgrade

    I upgraded my MacBook Pro last night, and have run into another glitch. I have been using my HP Windows Home Server as an external disk for Time Machine, and sharing media files across my network. After installation of Lion, my MacBook could no longer see the server and Time Machine is unable to function.

    I haven't spent any time yet trouble shooting this, but hopefully there will be a fix available either from Apple or MS to restore the functionality.
  • Lion install process = beta test.

    I feel like a guinea pig going through the very beta-ish Lion download and install process. There are so many bugs and irritations, it just feels so un-Appley. The AppStore download manager is primitive to say the least, pause / resume is pathetically broken and works 50/50. After the 1-day 3.7GB download after multiple abortions, the install process on my mac mini borked and threw up saying my disk was locked, and I was left with an unusable machine. Brilliant, Apple. Looks like you're competing with Vista.
    • RE: Watch out for little gotchas in the Lion upgrade

      @kraterz Perhaps they let the cat of the bag a bit prematurely (pun intended)
      • RE: Watch out for little gotchas in the Lion upgrade

        @imkain@... lol
    • Re: Lion install process = beta test.

      While I'm sorry to hear that you've had such problems, I think that suggesting this is an issue of the software / process being at a beta stage of development is grossly unfair. Problems come up with installs of all kinds of software and OSes. The fact that stories around the web show your experience is in the minority indicates that this isn't a "beta" issue, just a typical install problem. Even the complaints you offer about the App Store are a bit hollow, as download experience on servers when a hot new product has just been released always suffers.

      Again, I'm sorry about your troubles, and I hope that you can get them sorted out. Starting by reinstalling Snow Leopard as a clean install, then trying the upgrade again might be enough to do the trick...
      • RE: Watch out for little gotchas in the Lion upgrade

        @Snowy_River Hmm, I think I will implement in the future for my company, since experiencing awfully un-Apple install and upgrade chaos when the new IT guy network installed across the domain, a rule where the only people authorized to implement any type of manipulation of electrons (software developers, hardware engineers) will be individuals who actually hold degrees in particle physics. Clearly the mediocrity monster has finally caught up with Apple, so no more "software developers" or "network admins". Please post your resumes if you hold a MS in Particle Physics or higher and actually know exactly how to write code in a true mathematical format, instead of cut and paste cowboys.
    • how many similar cases?

      @kraterz That's pretty bad. I wonder how many other people have had similar experiences? As a company that focuses so heavily on OOBE, they should have been making sure that computer crippling situations like yours would be designed not to happen.

      Did you suffer any data loss? Is your computer still under AppleCare?

      They need to fix your computer and change their installer. Upgrade failure of that kind isn't acceptable.. at least not when you're paying for it.
      • RE: Watch out for little gotchas in the Lion upgrade

        @Hobyx I am sure you don't care if the number of cases is very low, only if it's high. I upgraded with absolutely no issues what so ever. I have heard of people having similar issues as kraterz but as was said earlier, no upgrade is perfect and as unfortunate as it is there are going to be some that have issues.
  • Lion

    So, the bulk of your issues (Exchange Auto-Discover worked flawlessly for me) relate to third party apps that hadn't updated in time for your test, and, oh, look, they're starting to now, eh? Pretty smooth first-day experience if you ask me. And anyone who's been keeping up (which, you admit, you were) knew Flash and Java were going to be no-shows at install time.

    So, Ed, what do you really think of it, now that your nitpicking is out of the way?
    • RE: Watch out for little gotchas in the Lion upgrade

      @kcsmith2 It's a perfect OS and predict it will overtake Windows by 2014.
      • RE: Watch out for little gotchas in the Lion upgrade


        Apple will never overtake Windows in the enterprise with their current mentality. They are a consumer-oriented company and most of the decisions they make are made with current or potential enterprise customers no where in their minds.

        I support a heterogeneous Mac and Windows environment, and I can state unequivocally that Apple doesn't make it easy on IT administrators. In fact, it's almost as if they are purposely confounding us at every turn.
      • RE: Watch out for little gotchas in the Lion upgrade

        You're absolutely right on both counts. Starting with the last few iterations of Leopard, they seem to be intent on isolating their machines from everything on the network that isn't sold by Apple. Obviously they have given up on making a dent in the enterprise side of the market...