Originally Posted by RogerD408

If you open your actual rez and scroll down, there should be a box with the upgrade info showing how many 500-mile upgrades are needed for each flight and a box to request the upgrade or words saying it has been requested.

Dumb question #1: Is this a paid ticket? You can't upgrade an award ticket.

Dumb question #2: Are you logged into your account and one of the travelers? Might not be able to request the upgrade if not.

If neither apply, call AA and see if they know why you're blocked from doing this. They may be able to do it for you.