Originally Posted by
jsloan
Welcome to FT!
Waitlisted upgrade priority is by status, then fare class; being an MPE cardholder doesn't help in this case. So, unfortunately, you actually
are literally at the bottom of the list.

While it's not impossible, a waitlisted mile upgrade request isn't likely to clear.
That said, you should actually consider yourself quite lucky. Upgrading EWR-SFO would normally have a $250 co-pay, and SFO-HNL $125. But it appears that EWR-SFO-HNL just has the $125 co-pay, and your upgrade request would be valid for both legs. (Either, both, or -- most likely -- neither, could clear).
Based on reports here, the cash upgrade price for EWR-SFO is likely to be about $300 (but it can be higher, and it can change). You may be able to take a buy-up now or on the day of departure. However, the online buy-ups appear to be broken currently -- there's a thread on this -- so you may need to call to get your buy-up offer.
Good luck!
Thank you for the response!
Pretty grim news, but basically what I've been expecting. I saw that the buy up is not available online, and hasn't been since I was ticketed back in July, but I assumed it was unavailable due to the popularity of the route. Good to know it might just be a glitch, I've been checking online periodically and was debating to call in.
I can't wait list the entire flight, since SFO-HNL is code share with Hawaiian. Since upgrades didn't seem likely for that segment and I"ll probably be stuck in coach anyway, I chose the 2-4-2 instead of 3-3 on UA.
If I wait list with miles +copay, would I still have an opportunity to buy up at OLCI? And if I do, I'd still get the miles + copay refunded? r/awardtravel is more pessimistic about the price, saying to jump on it <$500, but that it could go $1k