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Today’s little challenge was to sort out something which has annoyed me on and off since I got my iPhone: how to keep my various calendars in sync.

Let me explain the situation. I maintain four calendars: “Work” which originates in my office Outlook account and “Me”, “Family” and “Other” in my main GCal account. I would like all four to appear in Outlook, GCal, and on my iPhone plus, if possible, iCal and MobileMe. Easy? No, but I accept that I am trying to do something a bit complicated. Harder than it should be? Yes. I will spare you all of the combinations of software and settings that I have gone through, partly because I cannot remember them all, and focus on what I have working, which is almost all of it.

The link sequence and tools used are:

The main remaining issue is Outlook⇔GCal because Google’s program only syncs the main one in the account. There is a Windows MobileMe client that can overcome this but it only works if Outlook is configured in a certain way, which is not how my employer has it. At the moment I am using Google’s own sync program. There are others but the only other one I have tried so far (SyncMyCal) caused up a virus warning as soon as I loaded it. As my employer doesn’t like us installing our own software I will wait until we get Outlook 2007 which I understand does support CalDAV.

A critical part of the overall solution is Spanning Sync which links GCal and iCal. Until I tried this I couldn’t find a way to link a “native” iCal calendar with GCal. Spanning Sync is rather expensive ($25 for 1 year or $65 for life) so I am not sure that I will continue with this. I will use the next two weeks of the trial to look at alternatives.

What makes this difficult is the requirement for these calendars to end up in MobileMe, which will only sync with a “native” calendar in iCal. If you don’t need MobileMe (and I am still undecided about it) then use Google as the “hub” and subscribe to the calendars using CalDAV from both iCal and MobileMe, like this:

I should point out that the appearance in iCal is poor, with each Google calendar appearing in it’s own folder. But, it’s free!