• How do I earn 500-mile electronic upgrades / stickers?

AA awards GLD and PLT elite members four free 500-mile electronic upgrades for every 10,000 elite-qualifying miles (Miles Towards Elite Upgrades) earned during the membership year (Mar 1 – Feb 28). EXPs do not earn 500-mile electronic upgrades. Additional upgrades can be purchased online or at an airport kiosk for $30 each, or with an airport agent for $35 each.

500-Mile electronic upgrades do not expire and are not transferrable to other AAdvantage accounts (although they can be used to upgrade non-status companions traveling on the same flight).

Unofficially, elites can often get 1–3 stickers prorated at the end of the membership year to avoid ‘stranding’ Miles Towards Elite Upgrades by calling AAdvantage Customer Service (+1 800-882-8880) and requesting a partial credit. There is no set formula for this partial credit and this unpublished exception is made at the discretion of the individual agent. Emailing often gets poorer results in this particular case.

AA.com: 500-mile Electronic and EXP upgrades
FT: How to request prorated upgrade stickers at the end of February