Booking ORD-IAD-DXB and return in December for 2 Prem Plats (by then, both MMs). Upgrade with miles was available on the outbound from the outset, and I switched our return by one day to get 20A and B on the DXB-IAD, as consolation prize for no upgrade.

Booked us on a single PNR, but when I checked united.com 1/2 hour later to make sure everything looked ok, we weren't showing as waitlisted for the upgrades on the return

I immediately phoned and had us put on the waitlist. The agent couldn't see any upgrade availability for DXB-IAD, though we did get IAD-ORD (whoopee.) So I told her to split the record.

20 minutes after the email with the new PNR...poof! two upgrade emails. It doesn't make sense that the split did it - if it were RN2/R2 we should have gotten them anyway, right? - but you'll never convince me of that!

I know, we now have the risk downstream that we get treated separately in IRROPS or GA moves us around not recognizing that we are a group traveling together, but I'll take it, for a trip of this length.