Problem Using Systemwides to Upgrade Multi-Segment Itinerary

I'm sure other 1Ks have faced this problem. Itinerary is JFK-SFO-SIN, return SIN-HKG-SFO. Called to upgrade using Systemwides. Told that JFK-SFO and SIN-HKG cleared, but not the overnight segments. Agent wants to upgrade me on available segments, but I was told that if the overnight segments didn't clear , potentially after I had already flown the initial segments, I would be out two SWUs - they would have been wasted on short-haul legs. No chance of retroactively applying 500-milers or Region 1 to the domestic leg either. So I selected Y class seats throughout, despite the advantage of getting in the upgrade queue as early as possible. (UA 1K desk said they had asked UA management to change the procedure for years, but no change had occurred.)

Should I call them back and request the upgrade again? Other recommended strategies? What are the chances of the upgrade eventually clearing on the overnight legs for 11/22 outbound and 11/29 returning?

Thanks for input!

Request the upgrades for all the segments now and get on the w/l. I have not looked at the loads for the transpac segments, but you can always cancel your upgrade request up to the time you check in for your first leg...In these days UA's inventory management is pretty tight with the upgrade space and in many cases you won't clear until 7,3 or 1 day before departure (or at the gate).

Doesn't UA now say that the passenger can't withdraw an upgrade request once made?

you can't withdraw a request once it's CLEARED...but you can withdraw till then if it doesn't clear when you book it.

It is a bit of a crap shoot in that situation.

I just booked 2 tickets to ORD for mid Nov where the only confirmed segment was the SFO-ORD. Both 14 hour SYD flights were to be WL.

I picked days when C paid seats were at their lowest and PA waitlisted those. Came through in 24 hours which is pretty a much a record, as they often make you sweat until a week or so out.

Being a vacation I can be that flexible but know a biz traveller cannot.

Thanks for replies.

Let's say the SFO-NRT-SIN upgrades clear just before I depart JFK, with airport control in effect. Assuming typical no-show situation on JFK-SFO, will I have a problem getting UA airport staff to upgrade me JFK-SFO on the same SWU, or will they want a separate upgrade instrument at that time?

In similar circumstances, I have been asked how I planned to support a gate-clearing waitlisted first segment upgrade. Both times I pointed out that I had used a SWU to upgrade, hence I was holding C boarding cards for downline segments. The first time they pulled a e-CR1, which was quickly replaced without any intervention on my part. The second time they could see that an e-SWU had been pulled for the full itinerary.

Just mention that you already used a SWU, show them your SFO-NRT/NRT-SIN C boarding cards. Even if they pull a CR1 or 500 milers just take the boarding card and clear up the problem later.

Thanks, transpac.