PlusPoints strategy for connecting flights
 

For a flight to HNL with a mainland connection, the same number of PlusPoints are needed to upgrade both segments, and for an itinerary I'm considering, both segments are waitlisted. If I request both segments for the same 20 PlusPoints, if only the short-ish domestic flight clears, I'd end up being charged the 20 PlusPoints but not get the SFO-HNL flight, which is of course the more valuable use.

Is it better to just request the SFO-HNL to avoid the low-value use of only getting the short mainland segment? It'd be nice to get the whole journey, of course, but I would not want to end up using the 20 only for that first part. Any advice?

Thanks!

There isn't a universal answer -- you have to make the value judgement, depending on loads for your connecting ___-SFO flight and for your SFO-HNL flight. You do have the scenarios mapped correctly, you just need to assign chances to each and then decide what is the best expected value for you.

One way to get a slight clue about chances of clearing each is to check inventory (use expert mode). If you see one flight with inventory open like P9PN0 and the other like J9JN9C2D0, then the former is more likely to clear.

This is the current dilemma system-wide. Apply the points on the segs you're willing to spend them on.

One strategy is to buy an upgrade on one leg in cash (which are often pretty cheap) and then apply the PP on the longer leg.

Yeah, I think the general strategy to think of is "would I apply pluspoints to this segment if it were the only fight I was taking?" and go from there.

The general strategy that guarantee's you don't waste PP is to only use them when you can confirm at booking and to never waitlist. Ofcourse if you're sitting on a mountain of PP that are about to expire, then it doesn't really matter much what you do.

Since UA doesn't appear to clear most upgrades until T-24 hr or less, you could check your position on the upgrade list when it comes out 3 days or so prior to departure to get a sense of if SFO-HNL will clear or not. If it doesn't, then you could still cancel both upgrade requests. The risk is the off-chance that the shorter segment clears in advance of when the upgrade lists become visible.