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I used miles to upgrade once, but only got the upgrade right before boarding since it depends on availability. Being a higher-tier member seems to help get cleared earlier.

I once had better luck upgrading by checking availability through my United account a few days before the flight. If you're seeing high upgrade costs or waitlists, you might want to check options at https://travelbusinessclass.com — I’ve found deals there that were way better than what the airline showed me directly. Sometimes calling United after finding better rates helps too.