I've had mixed experiences with that. At least half the time, I still see on the reservation page a "upgrade from $xx" offer. Sometimes clicking through will even let you purchase; other times, I get "this itinerary is not eligible for upgrade." IIRC, you can call in and either inquire (probably meaning you're upfaring the ticket to whatever available F is being sold at that moment), or call in and ask to have your instruments removed (losing your place in line) and see what the site offers up once they're gone.

Most recently, I had TUS-DEN-IAD, with PP-supported, waitlisted upgrades applied. The reservation nonetheless offered "upgrade from $249" (or something like that), and clicking through, you could see that the total was around $700 (as the $249 was for the shorter segment only). It wasn't worth $700 to me, but I knew I wasn't going to clear, and I tried a fresh booking just to see what the actual F cost was, and came in with a sub-$500 delta from my current Y ticket if I simply changed the existing res or canceled & rebooked.

My wife was offered repeated upgrade offers on a recent SFO-SYD flight with PPs in play. She never jumped at any of the offers as the F cabin was wide open and her upgrade eventually cleared at T36.

offered $500 upgrade to Polaris HNL-SFO, it's a redeye. Seems like it's somewhat the normal price now? I paid $370 last year for the 77HD. Should I grab it at this price or do you think it'll go lower? Flight is 2 months out with roughly 20/60 seats taken.

$600 EWR-LAX at check-in - 752 slimline aircraft
Too rich for me.

"MileagePlus miles will be credited based on original purchased class of service"

I assume this means no PQP credit for the buy up?

There will be PQP credit.

No (award) miles.

This depends on your risk tolerance. I think it’ll go lower (as low as $350) or stay $500 until it is 50/60. If you are comfortable with $500 and want to select a seat go for it.

My datapoint is twice a month out of HNL on the redeye but things can change.

Appreciate the response. The upgrade went back up to $1k+ but I think it'll drop again as the seats are still the same in the front cabin. I think I'll bite at ~$400 as I'd need to get 6 seats.

I am guessing there is a really good chance that if the offer goes down to $400, not all six seats would be available to u/g at that price.

I never get any of the cash UG offers once I've applied PPs. In fact I often see text stating that no UGs are available when I try to force a cash offer. Is there something I can do to change that? I'm much more interested now that PPs clear infrequently.

There is little to be lost cancelling the upgrade, checking and reapplying. Sometimes, you can call in and get a quote. Generally, on a Polaris or non-cpu route the offers are not visible. but there seems to be exceptions.

I wish I found this thread a week ago! It is a bit complicated but will try and be concise and will for sure up date on how this turns out and what and when we get offers.
Flying BOI-SFO-HND 5/30
Return KIX-SFO+BOI 6/6

It is a delayed school tour due to covid, wife retired and her students are now in college now.

I joined the tour just a few weeks back, we did not get confirmation numbers till last week Tuesday. Surprised when I got my ticket to find I am in PP for SFO-HND and eco plus BOI-SFO.
I am on a separate res number from them, they are in economy.

So far no cash offers to upgrade for either her or I. We have also talked with the tour agency once, and with United four times to at a min to get my wife re ticketed to PP so we can sit together plus she deserves it.

They point fingers at each other. Agency says United needs to do it United says agency needs to do it. We have both received mile offers starting at 30K going to 30K plus $, but that would only waitlist either of us.

It is ridicules, you are willing to pay cash for a guaranteed seat upgrade but united does not want your money! Also they put her in the worst seat, last row limited recline. I can move her to eco plus or preferred seat but that is not my goal.

Going there are seats in all classes, returning PP is full but they will still sell me 2 PP round trip seats ( I realize some current PP
seat holders will be upgraded and also checked in expert mode).

I could of gotten a PP round trip at one point for $2500, only $300 more then $2200 Economy, last I look it was $2800 for PP

Edit; Question:
If you waitlist with miles, will you still get offers to pay cash, and will that cancel your waitlist and not charge the 30K miles.

Sounds like an IT-fared ticket. Basically the tour operator has a non-published contracted fare you're ticketed. United won't touch the ticketed fare construction on those which is why they send you back to the tour operator. The tour operator probably doesn't have either a contracted fare or anymore availability (if your ticket is actually booked under the tour contract) for that tour code/route for PE, which is why they say UA has to do it. If the tour agency won't do it, your only option is going to be if the system gives you a cash buy up offer, but no one over the phone at UA would be able to force it without that, absent selling you into a published fare.

Lux Flyer I think you summed it up fairly well, what is interesting is both side are pretty emphatic that the other is the only one that can change anything. Neither is saying it is too late to change or it can't be changed just that they are not the ones who can do it.
So the burning question is do we put in for 30k mile waitlist on her ticket or wait to see it the money option appears? Think I will give it till Tueday (one week out to check in) then decide.

EWR to IAD, last seat on E70 upfront - asking price $1,227

Should I do it? Lol...