Boy, this is difficult. I have a flight booked with PlusPoints attached for this upcoming Tuesday. I am not showing any possibility to upgrade with cash. Both the app and web say "Not Available" even thought it is. A family member is traveling with me without PlusPoints and the upgrade price is very reasonable. Is the only option to remove the PlusPoints and hopefully the upgrade offer will populate? The other issue is that the second leg of the itinerary is already upgraded. Not sure if I will lose that upgrade. I didn't realize this was so difficult. I even tried to Change Flights and it is not showing leg where I am already booked in coach with the PP attached. It's amazing you can't see the $ upgrade price. I thought UA was all about the "benjamins"? Any suggestions? I guess another option would be to just cancel the whole ticket and rebook. Surprised at the difficulty. And, hate how the app punts me to the web. Why?

Yep, you need to remove the pending Plus Points from that flight and then you will see the options. It's bizarre but that is how it appears to work.

Brutal. Thanks.

Yes, BUT

If the same PlusPloints for both flights, then no can do.
If the second is a return flight, second set of PlusPoints, then you can remove the PlusPoints from the first with no fear.

You can remove the PlusPoints if no segment has cleared yourself
https://www.united.com/en/us/manageres/mytrips?tab=pp

If you don't get the offer or don't like it, reapply the PlusPoints

Call 1K line to get an offer. Take it if reasonable. But you will still lose PlusPoints for the other leg.

Total missed opportunity - "your upgrade is waitlisted with plus points, but BUY NOW the upgrade for $xxx"

I am currently experiencing this frustration! I can do StW but only to PremiumPlus. If they can show me StW then surely UA could show buy up prices when PlusPoints are applied.

With StW I am more likely to use a combo of StW for some flights and buy up for other flights. Instead if I have PlusPoints applied I have to wait until OLCI for the buy up. Missed money making opportunity for United to get my money earlier.

I was just in this situation today, sitting #1 on the upgrade list at check-in with 1 seat available in PremPlus, waitlisted on the first leg and confirmed in Polaris on the second leg. FWIW I saw upgrade offers after checking in.

I have been way down the list for a PP upgrade - I've called reservations in the past to cancel my PP upgrade and have the agent say, "There is a seat left for upgrades", then re-input my PP UG request and cleared me. JUST ONE PHONE CALL!

That was because PZ was 1 when you called. The agent helped you to cut the line. You could do it yourself, though, without calling.

Not sure if something is broken on one of my reservations, but I booked a flight last week (3 class transcon) that is allowing me to apply plus points and still see pricing for premium plus and business. I'm somewhat hopeful this becomes the norm. If not, I can't imagine how it the options would be there.

After you applied +Ps you are still seeing UG offers?

Just checked again - my mistake. It's a MUA(waitlisted). But I still see cash buyup offers under upgrade although no choices for PP or miles. Perhaps this is normal behavior. And now I'm trying to figure out why I picked miles over PlusPoints.

For all the legs? Or just the legs where you did not apply the miles. I don't apply PlusPoints to domestic legs on international flights and can see uograde offers for those legs.

Two segments on the reservation - non stop outbound and non stop return, EWR-SFO on a Polaris 777. One I upgraded with cash and the other is wait listed, but still showing upgrade options for money.