Originally Posted by paterwdb

Assuming that you are on the same fare classes in both directions, here is what you would have to do:
1. Separate the PNR. There is really no reason to keep them together.
2. You can list for the upgrade on the T flight. You can't list a companion unless they are on a K or higher fare.
3. Then, after your T flight out, but before your return, you can list your companion (as long as comp is K or higher) for the upgrade. Since the PNRs are separate, the comp will not pull you down in the upgrade lottery.

The only down side of separating the five of you on the PNR is that if, for some reason you were irrop, the system wouldn't know to try to keep you together on auto-rebooking. But that's a risk worth taking, I think, to possibly upgrade a buddy.

What's the routing? Your friends here could probably tell you the likelihood of getting all the way to a Comp UG on the route if you give us cities and times of day.