Based upon the UAL UDU faq: Can I use Unlimited Domestic Upgrades when traveling with friends or family? Yes, we’ll automatically request Unlimited Domestic Upgrades for all elite members and up to one companion traveling on the same reservation. When upgrade space becomes available, requests will be prioritized by the Mileage Plus® elite member’s status, booking class purchased and by time of ticketing.

I booked two tickets, wife and I, six months ago and applied for upgrade at booking time, called before the flight to assure the e-500's were changed to UDU's and we were both on the same pnr as well as waitlisted together. Agent agreed all was proper. Surprise at the gate when the "board" said 3 seats available with me # 2 and my wife #8. I asked GA and she said that's the way it works...wow, great idea United, great change...not