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I think I've found a way to sync OF at home to Outlook at work Thread Tools Search this Thread Display Modes
Here's my setup

Work PC:
Outlook with GTD plug-in
Sync to Windows Mobile handheld

Home Mac:
Missing Sync for handheld to iCal
OF-iCal sync

-Tasks created in Outlook have the category set the same as the context. The contexts come into iCal as separate calendars.
-Tasks created in OF sync to the corresponding iCal calendar

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