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How To Upgrade Your MobileMe Calendar Safely

If you’ve been waiting to upgrade your MobileMe Calender to the “new” CalDAV model, the deadline of May 5 is fast approaching. Since my business runs on iCal, I approached the upgrade with reluctance and some healthy fear. Here are my recommendations and a walkthrough of the process that should hopefully make the task less daunting for you.

Backup, Backup and Backup

No matter what backup solution you use (Time Machine, online, manual), now is the time to run a full backup just in case. Additionally be sure you’ve synced all your iOS devices to your Mac. If you do “over the air” syncing you should be fine.
Just to be extra safe, I ran two additional backups within iCal. Under the File Menu in iCal is the Export Function. First, create a full iCal Archive under the Export Menu. That backs up your entire iCal calender list en mass. However, I alo backed up each and every calender to an .ics file by choosing each one and then going to File, Export, and then Export. This backs up each calender manually.

Log Into MobileMe and Begin the Process

Now that you have triple redundancy on your calenders, you can begin the process. Log into your MobileMe account via Safari (just to play it safe don’t use alternate browsers) and then click the icon in the upper left for iCal, which is the familiar spiral day-at-a-time calendar icon. You should be presented with a window reminding you to “Upgrade to the new MobileMe Calender.” Click “next” and you’ll be presented with the system requirements. Since CalDAV only works with Leopard or Snow Leopard, Tiger’s been fully de-clawed for iOS. If you fail to move to CalDAV your MobileMe calender sync won’t work unless you move to 10.5 or 10.6 and if you do, Tiger will no longer sync without a third party helper like BusySync.
After confirming your devices meet the requirements, click “Upgrade Now” and the process begins. You’ll see a series of conformations that the calenders are being prepared and upgraded.
What’s happening in the background is your existing calendars that were synced with your computer and MobileMe are making their move off your computer and into the cloud. When complete, your calenders exist on MobileMe servers and your iCal merely provides another way of accessing them. Your iOS device should be smart enough to notice the change and modify itself as well. Now your calenders will exist on MobileMe’s servers and your other devices merely access the data, similar to the way IMAP works for email. Syncing is virtually instant since modifications are transferred directly to the cloud.

Trust, but Verify

Just to play it safe, I had some preset test routines ready to make sure everything when smoothly. I waited about 20 minutes to do the following to make sure all the changes propagated:
  1. Add an item via iCal and verify it shows up on my iOS and Mac OS devices and MobileMe’s website
  2. Add an item via each iOS device and verify it shows up on all other devices
  3. Modify an event on each device and make sure that change shows up
  4. If you have any calenders shared with someone, make sure they follow steps 1-3 for your calendar and you do the same for theirs, after they’ve also performed the upgrade

Snags, Errors, and General Weirdness

If all goes well, you are done! However with computers, everything doesn’t run so smoothly all of the time. In my particular instance one of my calenders was somehow corrupt enough to not make the move to the cloud, but I could still access it on my desktop. I kept getting errors in the upgrade process until I deleted the calender from my desktop. After the upgrade was complete, I then imported the .ics file I backed up earlier manually. It work, but if it hadn’t, I was going to use Time Machine to restore a version that wasn’t corrupt and then I’d again move it to MobileMe manually.
I was a big user of BusySync and BusySync has specific instructions and caveats on how to make the move with their software. As for other secondary services, I’m disappointed that syncing with Google became more complex after the upgrade. I had to manually add my Google shared calenders.
Once the upgrade is complete, the way others subscribe to your calender has changed. They now can have both read as well as write access to your calenders and most likely you’ll manually have to invite them to your calender by using the Share command under the Calender Menu within iCal. I had to manually re-invite people.
Another snag I personally ran into was on my MacBook, when I first launched iCal, it kept all the old calendars and then MobileMe created the proper CalDAV settings automatically but kept those old local calenders so everything was duplicated.
Two great websites to help ease the transition are here and here. If you ran into any snags or have any suggestions about upgrading your MobileMe calander, be sure to let us know in the comments.