My Travels with Lion & iCloud: The Claws Come Out

This is part II of a software upgrade extravaganza: the newest Parallels Desktop, Mountain Lion, the Messages beta and iCloud calendars.


After some fairly routine stuff, covered in Part I of my Lion travelogue, this was the stuff I was looking forward to. I had already installed Lion (10.7.0) in Parallels Desktop right after I upgraded the iMac itself to Lion. I did that just for the fun of it, and it is, of course, legal according to Apple’s license. Having Lion in Parallels (in Lion!) provided me an easy path to the Mountain Lion upgrade without risking an install on the naked hardware. That way if something were to go wrong, I could just delete the virtual machine and start over.

The first step was to upgrade to Parallels Desktop 7.0.15050.707095, which according to the company, “adds experimental support for OS X Mountain Lion Developer Preview as both a host and guest.” That means that you can both 1) run this version of Parallels in Mountain Lion (host) or 2) run Mountain Lion as a guest OS inside Parallels.

Parallels 7

Parallels Desktop

The ML download you get from Apple is, itself, an application whose package contents contains a .dmg file. (To view an app’s contents, right click the app -> Show Package Contents, then drill in.) I decided that the easiest way to proceed was to 1) use Software Update inside the Lion VM and update to 10.7.3 with a combo updater and then 2) use the ML Install app to upgrade the Lion VM to Mountain Lion DP1. I could have used shared files between the host and the VM to transfer the installer and the combo files, but I was in a hurry, so I just used a Flash drive.

Parallels Flash drive option

Parallels USB Flash drive option

One of the really cool things about Parallels 7 is that when you insert a USB Flash drive into your Mac, Parallels asks you, with a beautiful graphic, which OS should mount it: the host or the VM. That pleased me greatly, and sped things up considerably.

From there it was all down hill. I applied the Mountain Lion DP1 update over the Lion VM and, and then the VM rebooted. This is going to be a fun exploration.

Don’t Kill the Messenger, Well, Okay, Sure

You just knew this smooth sailing had to crash into the rocks, and it did. My next task was to install Apple’s beta of Messages in Lion 10.7.3, and while the install went okay, I just couldn’t get beyond the registration page in the setup with multiple attempts over a week’s time. Some consulting help didn’t get me through this either.  Here’s the error I got.

Messages error

A delete, a new download and a reinstall were tried several times with no change in the ability to login with my Apple ID. On about the third reinstall, however, the standard iChat window of buddies appeared, and a chat window also appeared. Amazingly, I was able to send and receive chats. That boggled my mind.


Amazingly, it still worked

How it is that I can launch the app and send messages without being signed in remains a mystery. Beta software. That’s it.

Time’s up

The final task on the list, encouraged by the success with contacts was to move my calendars into the iCloud. That basically means using the iCloud pane in System Preferences and checking the calendar box. (In part I, I described enabling iCloud.)

I don’t use iCal because I prefer (and love) BusyCal. BusyCal draws from the same data source as iCal, so it’s a great replacement. I had been using BusyCal and cross published calendars between Macs. That seemed okay in the past, but as my wife and I added calendars, that process was getting somewhat unreliable. So I decided that using iCloud as a master source to drive all our calendars would be more elegant. The procedure I used is described by BusyMac.

On two of the three Macs, iCal locked up solidly during the initial iCloud sync, and I had to force quit. However, even when I subsequently pointed BusyCal at iCloud, things seemed to be okay at first.


When eveything’s ready, you point BusyCal at iCloud

Finally, I deleted the local calendars on the Macs. Then I went to each iOS device and enabled its iCloud calendar. At about this point, I noted that calendar entries on my Mac Pro, the main family calendar, were starting to double and tripple up. I’m not quite sure how this could happen because duplicate calendar entries should be really easy to detect, but it did. It may have been due to that iCal lockup mentioned above. I wasn’t terribly annoyed because there weren’t many entries to fix, but I can see how this could greatly annoy someone who has lots and lots of calendar entries.

The net result is that I now have all my Macs and iDevices syncing calendars with each other.  Now, when I make an entry on a Mac, all the other Macs, and then the iDevices, are reliably updated very soon afterwards. It’s a glorious thing to behold, watching those entries magically pop up on other devices, one by one, like prairie dogs.

The End of the Road

That’s a far as I’m going to go for now. With all Macs on Lion, all email, contacts and calendars encrypted and synced to iCloud, Messages limping along, and Mountain Lion nestled in a VM, I’m done as much as I’m ready to do right now. The wise thing to do is to sit back, cruise along, and see how things go before making any more radical changes.

With fingers crossed, I was braced for the worst, and it didn’t happen. I think the reason was that 1) I kept several of my Lion Macs relatively simple, without any hacks, 2) I was fully backed up everywhere (not tempting fate), 3) I did some reading and worked out some step-by-step checklists, and 4) (probably) benefitted from some good code from Apple and not jumping into iCloud on day one last October.

I love lab days.


Lion Cub credit: Shutterstock