You really cannot trust UA's IT I am afraid. Sad but true.

I realize that these may appear to be stupid questions but between CPU and GPU and Y/B/M and Y,B,M,E,U,H,Q,V or W class I’ve completely confused myself.

1: For an international flight, if R booking class is available and a Premier 1K with an available GPU has a purchased 016 ticket in Y,B,M,E,U,H,Q,V or W booking class, that person can call United to request the upgrade and the upgrade should be cleared at that time?

2: Exact same question and parameters as #1 except Z,P,S,T,K,L,G or N booking class. The UA agent should say “no, that booking class is not eligible for an upgrade”?

3: Exact same question and parameters as #1 except no R booking class available, the request will go to a waitlist?

4: If waitlisted, more than 24 hours ahead of flight time, one cannot know or be told (by a UA rep) the number of people waitlisted (for an upgrade) nor one’s relative priority position on the waitlist?

5: If waitlisted and number one in priority, if and when R booking class becomes available, the upgrade should clear automatically? But that doesn’t always occur and sometimes it’s possible to call and have the upgrade cleared? Even if one is not number one in priority on the waitlist?

Thanks very much. I appreciate the assistance with helping to stop my head from spinning. ;)

Yes. Or just apply it yourself online.

Correct.

Correct.

They can tell you (although some will decline to give that information). What they say may or may not be true. Regardless, it's not going to be a reliable indicator of upgrade odds.

Correct. In fact, if there's open R, you can call and jump the queue for the upgrade, regardless of position on the waitlist. It may take more than one call to find an agent who will do this.

Thank you very much Kacee, greatly appreciated.

Hopefully some good news for GS upgrades. I applied 2x GPUs from a GS account to a Gold traveler's PNR yesterday. The GS Rep told me at the time that there were 0 GS's on the waitlist (all had cleared) but that there were 6 1K's on the waitlist. At the time there were 15 open seats.

At ~6:37am PST I received the Waitlist Notification email that the upgrades had been confirmed. I logged on to see that it did indeed confirm into PN and that there were now 13 seats left (so none of the 1K's had cleared). While it was only ~6.5hrs into the 4/15 change, it seems promising to me.

That depends entirely on one's perspective.

Although it won't really be a surprise if gifted GS instruments continue to clear into PN, effectively rendering UA's "new" traveller-based priority scheme meaningless in these circumstances.

RPU upgrade strategy on PS; 2 separate tickets
 

I booked myself on a SFO-JFK-SFO itinerary at the end of June (S Class). I booked my friend on the same itinerary a couple of days later (S Class as well) so we have separate reservations. I have two RPUs that I'd love to use and the goal is for us to sit in the same cabin for each leg: both in BusinessFirst on the way over and both in Economy on the way back (or vice versa). Not surprisingly, upgrades with RPUs are currently waitlisted.

1/ Should I waitlist both of us now on one of the legs and hope that we both clear together (I'm Plat; she's General Member)? What if I'm the only one who clears? Can I decline the upgrade? Of course, if I do that, there is the risk that my exit row seat next to her might be gone...
2/ Should I wait until, say, 100 hours before departure and see if RPU upgrades are available for both of us at that point?
3/ Should I just check us in (making sure we're together in Economy) and wait until we get to the airport to see if we can both be upgraded on my RPUs?

Any insight/experience would be appreciated. Thanks!

In my experience, R (if there's any space available) opens up T-24 at the earliest. You will need to watch like a hawk for the space and call in as soon as it becomes available. Also: unless you're traveling at an off-peak time, good luck with two seats. I typically have to SDC just to find one.

This is now a real challenge if you book on separate PNRs.

Your best shot of both getting upgraded comes if you both waitlist now. But there is a very real risk you will wind up flying in separate cabins. If you do this, continue to check frequently for R and call it in if you see open R.

Chances of both clearing using either other approach is lower. No. 3 is particularly unlikely to work.

The other thing to do is try to SDC into open R at T-24. Unfortunately, UA is much less likely to open R at the 24 hour window than it used to.

Waiting will never help on priority.
A GM member will unlikely clear, if at all, until the gate. (note as of today the waitlisted passenger is prioritized based on their status, not yours).
You can decline an upgrade but the economy seat choices will be limited.
Personally I would put the odds for both clearing as low but definitively not until the gate (and then seating together may be an issue).

The post checkin R opening has decreased this year (things are being pushed to the gate to allow more time for upsells).

Thanks for all the responses. I had an idea it was going to be very tough...

I'm taking JFK-SFO tomorrow and had put in RPUs for the upgrade for myself and my wife. It's 99% not going through (BF is fully booked on the plane, so think a lot of people will be SOL), but I was curious how long it takes for the RPU to be re-deposited into my account - there are other itineraries I've already booked that I'd like to throw the RPU towards if it doesn't go through tomorrow.

I'd just call it in as soon as the flight is over - I cancelled a flight this week that had a successful RPU application, and of course the RPU just stayed in limbo. Because, UA IT.

I haven't had many RPUs fail but they are usually back in a day or two. If irrops or other irregular situation is involved it may take longer.

Very tough route. I flew it yesterday and Tuesday are not the busiest day to fly. As a 1k on an E fare, I was #8 on the list. I didn't clear as you can guess