Almost as expected, there would be some Outlook 2011 issues with the introduction of iCloud this week. But this time, I blame Apple as much as I normally blame Microsoft.
For me, the issues was that my Outlook calendar went missing (as always). As many Outlook users, I use Sync Services to sync between Outlook and iCal, and therefore with my iPhone. But after I installed the latest Lion update, that laid the pavement for iCloud, and signed up for it, the Outlook calendar went blank. All of my calendar entries remained in iCal, but they did no longer talk.
Maybe a simple fix for this would be to turn of iCloud for my calendar, and just continue to sync that old school? Well, it turns out that when you turn of iCloud for the calendar, it removes iCloud content: And iCloud content means your entire calendar, even if the entries originated from iCal to begin with. Nice feature, Apple! If you turn it off on the iPhone, you can choose if you want to keep the calendar entries.
If you try to export your iCal calendar as an iCal archive, turn off iCloud, and import, the iCloud will be turned back on automatically.
So my solution to keep a happy sync between Outlook and iCal, was to export each calendar (for some reason I have many) from iCal as .ics-files while on iCloud. Then turn of iCloud, import them in iCal, and we were back were we was before the update. If you want to merge some of your calendars you could do so, or keep them separated.
(Update 14/10: As Ian points out in his comment below: If you have a Time Machine backup of your system from before you turned on iCloud, you can use that for a roll back.)
Another solution would of course be to abandon Outlook, at least until something pulls out a finger from somewhere, and fixes this.
So now I can once again sync Outlook with my iPhone. Surprisingly, the address book sync works like a charm.
Maybe I’ll just go back to pen and paper.