Watch out for little gotchas in the Lion upgrade

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.
Written by Ed Bott, Senior Contributing Editor on

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.

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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.

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