check out these posts for answers:

http://www.flyertalk.com/forum/showthread.php?t=876087

http://www.flyertalk.com/forum/showthread.php?t=872011

If your upgrade doesn't clear before you check in, you can transfer yourself to the departure waitlist at the airport when you do check in - either using OLCI or by phoning after you've checked in to make sure you've been transfered.

If you are still waitlisted before doing OLCI, you won't be able to check in on-line unless you remove yourself from the waitlist, check in, then add yourself to the departure waitlist.

Good luck.