• How many 500-mile electronic upgrades / stickers do I need and when must I have them?

Each increment of up to 500 miles for a given flight segment requires the use one 500-mile electronic upgrade. Thus, a 1100-mile flight requires three 500-mile electronic upgrades. AA does provide an unofficial ‘grace window’ of 51 miles on the total mileage, so a 1051-mile flight will only require two 500-mile electronic upgrades. EXP upgrades are complimentary and do not require 500-mile electronic upgrades.

Elites can request an upgrade for one companion traveling on the same flight (not necessarily the same itinerary or reservation). As of Jul 2009, if both passengers are elites, 500-mile electronic upgrades will be debited separately from each member’s account. (Previously, the default was to debit the upgrades from the requestor’s account, which could be overridden at the airport by asking an agent to remove the ADC code on the Passenger Item List after the upgrade had cleared.)

Passengers do not need to have any 500-mile electronic upgrades in their accounts to request an upgrade online, but do need to have enough stickers in their accounts at check-in if the upgrade has cleared in advance, or if they would like to add themselves to the airport upgrade waitlist if the upgrade has not cleared in advance. 500-Mile electronic upgrades are only debited once the flight is completed.

AA.com: 500-mile and EXP upgrades
FT: 500-Mile electronic upgrades / stickers pulled separately for elites traveling together
FT: 500-Mile electronic upgrades / stickers “51-mile Grace Window” (consolidated)