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!