Going abroad with my boyfriend over New Years. United 1k and waitlisted with plus points on both legs right now. Any tips on how to get these to clear/upgrades confirmed?

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See if the destination/dates are eligible for a skip the waitlist upgrade.

Alternatively, book the ticket on points and as you get closer to departure, see which flights have availability in the premium cabin and swap flights accordingly. Given your dates of travel, this likely won’t work though.

Otherwise your main options are either pay for the upgraded cabin or pray the upgrade clears.

Nope but to keep an eye on PZ inventory. Give them a call as soon it's available

Oh yes, here is the rule - the priority in which plus point upgrades are given is —
1. Paying passengers
2. Class if fare, if you bought the cheapest(based on fare class not dollar ), you are not in the front
3. Your status
4. The price of the ticket

Bottomline- buy the flight with most empty seats and in a fare class which is cheap enough but the higher one ;) got upgrades for a party of 3 on a 15 hour flight earlier this year

You can pay the difference in fare class even after you bought the ticket to increase your changes.

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