I finally got my calendar (in iCal) syncing with my BlackBerry via PocketMac. The solution is ugly, but it works.

Here is what I did:

1. Back up all my iCal calendar data on my Mac, in several formats just to be safe.
2. Export my calendars in iCal format.
3. Write a little script to split the calendars into 2006 and pre-2006 versions.
4. Delete all the calendars in iCal.
5. Delete all the calendars on my BlackBerry.
6. Reset Sync Services data.
7. Reboot the Mac.
8. Add the 2006 calendars back, one by one, syncing after adding each one.
9. If the sync failed, repeat steps 4-7 after manually editing the iCalendar and pulling out any data that looks like it could cause problems.¹
10. Wait for the next version of PocketMac to come out that will let me to choose which calendars to sync, and will allow me to put my archived calendars back into iCal.

Now I’ve got a working solution for keeping track of appointments on my mobile device. It’s not ideal, but hey – little on the BlackBerry is so far. I’ll add a post on my solution for multiple return e-mail addresses later.

1. Big descriptions seem to be the main culprit here – generally travel info created by Expedia or pasted from an e-mail. [back]