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I've got a little problem, I need to be able to have a reoccurring event (forever) that marks the day after the second Tuesday of each month.

Your probably thinking, why not just Wednesday of each month. October 2008 is an example, it starts on a Wednesday. :(

Really I just need it in Outlook, probably (but not limited to) some iCalendar format file.

+1  A: 

The following iCalendar rule should work:

RRULE:FREQ=MONTHLY;BYDAY=WE;BYMONTHDAY=9,10,11,12,13,14,15

It should be read as "The first Wednesday of every month that falls on the 9th or later".

Edit: To use, create a calendar with a recurring event and export it to .ics. Open the ics file, find the existing RRULE, replace it with this one and import the ics back into outlook.