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Mileage upgrade question

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We may not be frequent fliers by standards of many FT members, but my family does usually usually take round-trip flights twice per year or so. Over the years we've finally saved up enough miles to upgrade all 3 of us to F on a domestic flight. I've searched the possibility for an upcoming EWR-RSW flight we will be taking and it is available for 20k miles/person. My question is more about logistics. One of our accounts has 40k miles on it and the other has 20k. I know United will let you "sponsor" an upgrade even if your account is not the one used to make the reservation. But will the system let me just upgrade 2 passengers with the one account and then come back and upgrade the 3rd with a separate transaction? Would that work through the United website or will I most likely have to call reservations to arrange it? Thanks for any insight. I'd just like to get an idea of what I am getting myself into before I do so.

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