True confession time here. While I have upgraded to Mac OS X 10.7 Lion on my MacBook, I’m still running 10.6 Snow Leopard on my Mac Pro. The reasons shouldn’t surprise anyone: Rosetta, needing a Snow Leopard test machine, and not needing Lion’s new features. Oh, and inertia — I have work to do, and installing Lion on my Mac Pro in the way I want to do it will take some time. None of these problems are insurmountable, and while Lion doesn’t do much for me when I use my MacBook, I don’t have anything against it either — I get my work done with applications, not the operating system.
But lagging behind Lion also meant I was hesitant to upgrade my MobileMe account to iCloud, since I didn’t want to lose access to my shared MobileMe calendars on my Mac Pro. That wasn’t the only machine in the mix, since I also access those calendars on an original MacBook Pro that can’t upgrade past Snow Leopard, and our Power Mac G5 file server that’s stuck at 10.5 Leopard. Also included are my iPhone 4 and iPad, but since both of those run iOS 5, iCloud presents no problems for them.
Pushing the upgrade was the household tension created by Tonya upgrading her MobileMe account to iCloud while writing “.” We normally rely heavily on shared calendars, but her upgrade to iCloud meant that she could no longer share my MobileMe calendars, and sooner or later, that was going to result in an awkward scheduling conflict.
I’ll bet there are people out there who have put off iCloud upgrades for similar reasons, but to reveal something I didn’t realize until the end of the process, the most recent version of BusyMac’s simply solves the problem, enabling Macs running Mac OS X 10.5 or later to share iCloud calendars. (BusyCal costs $49.99 for one Mac, or $79.99 for up to five Macs.) That doesn’t mean you should just switch to iCloud without considering other aspects of the move, for reasons I’ll discuss later, but BusyCal 1.6.1 does remove one significant barrier to the transition. Before finishing the process, I had thought I would bring my older Macs into the mix by publishing my shared iCloud calendars using BusyCal’s local network-based BusyCal-to-BusyCal sharing. Although that would have worked, it turned out to be unnecessary.
Thanks to Rich Mogull’s near disaster with iCloud (see “,” 2 November 2011), I wanted to perform my move extremely carefully. To that end, I pored over the relevant section in Joe Kissell’s “ ,” which has helped thousands of Mac users make the iCloud transition, and then I correlated his instructions with  making the jump.
I won’t reiterate everything I learned from those two sources, but here’s the basic approach I took, and what I’d recommend to others in similar situations:
On each of my Macs, I backed up BusyCal (File > Back up BusyCal), iCal (File > Export > iCal Archive), Address Book (File > Export > Address Book Archive), and Safari bookmarks (File > Export Bookmarks). I have plenty of system-wide backups, but my experience is that if you prepare for problems, you won’t have any.
On BusyMac’s advice, I reset BusyCal (Help > Reset > Reset BusyCal) on each of my Macs to ensure that each one would be starting with a clean slate.
On my MacBook running Lion, I opened the MobileMe preference pane, and clicked the Move to iCloud button. That loads a Web page at
https://www.me.com/move/, where the next steps take place.
I worked through a number of Web pages that merely confirmed that I was using the desired account, that my calendars would be moved to iCloud, that I could keep using certain MobileMe legacy features until 30 June 2012, that MobileMe syncing would stop working, that my Macs and iOS devices were running the right operating system versions, that contacts and bookmarks would come from my devices and not me.com, that I had a backup, and that I had agreed to the iCloud terms of service. Phew! After I had acknowledged all that, my MobileMe content was moved to iCloud relatively quickly.
Once it finished, on BusyMac’s suggestion, I next launched iCal on my Lion-equipped MacBook, and let it sync entirely with iCloud. (Remember, iCal under Snow Leopard and Leopard cannot communicate with your iCloud account.)
Still on the MacBook, I launched BusyCal itself, and it connected to iCloud and synced all my calendar data.
I went to all the other Macs and launched BusyCal on them, and acknowledged alerts on my iOS devices that I’d switched from MobileMe to iCloud. This was the point where I was surprised, since BusyCal on my Mac Pro automatically connected to my iCloud account and brought in my calendars, eliminating the need for me to publish them from my MacBook. On the other two Macs I had to choose Calendar > Connect to iCloud/CalDAV Server and enter my iCloud account information to get them to make the connection.
Lastly, I shared the calendars that Tonya and I use together; this can be done from either iCal or the Web-based Calendar app on iCloud — I think it’s a testament to how confusing iCal has become that I found it much easier to share the calendars from iCloud’s Web app. (In the Web app, you just click the little radio wave broadcast icon next to the calendar name in the sidebar; since iCal replaces the sidebar with a funny popover, it’s difficult to figure out how to select a calendar and choose Calendar > Share Calendar.)
Again, I’m a little embarrassed that I had equated iCloud compatibility so completely with Lion that I didn’t realize BusyCal would enable me to access all my iCloud calendars from my Leopard- and Snow Leopard-based Macs.
There are a few casualties associated with switching to iCloud, only one of which is a significant concern. A number of types of data, including Dashboard widgets, Dock items, Keychains, Preferences, and Mail accounts, rules, signatures, and smart mailboxes, after you move to iCloud. That’s also true of independent applications that rely on Mac OS X’s sync services to sync data across Macs — Transmit, Yojimbo, TextExpander, and more. None of this is a problem for me, and  often provides a viable alternative for MobileMe syncing. It’s likely that future versions of MobileMe-savvy apps will eventually support iCloud syncing.
More concerning is that I lose Address Book syncing with any Macs that are not running Lion. Contact syncing with non-Lion Macs is much less important to me than calendar syncing, so I’m willing to live with it until I get around to upgrading my Mac Pro to Lion.
There’s also one workaround for contact syncing that I’m investigating, and I’ll write more about it once I’ve had a chance to test it. (it predates Apple’s use of the name in Snow Leopard Server) promises to enable contact and calendar syncing on a local network, and better yet, it’s currently free. From what I can tell from the product’s Web site, it would enable me to set up my Power Mac G5 as a server, share contacts to it from my iCloud-connected MacBook, and then have my older Macs connect to the server for changes. Leave a note in the comments if you have any experience with Address Book Server.
In the end, although the move to iCloud would have eliminated calendar sharing were I relying on iCal, the fact that I far prefer BusyCal in every way means that the transition was easier than I had anticipated.