My understanding is that an annual pass is activated as soon as you purchase it if you purchase it at WDW. Park entry is not needed to activate just issuance of actual pass which you can only get at WDW. When you purchase in advance from home, either online or by phone, you do not get the actual pass until you show up and get it at the ticket booth or guest relations at the park.Thus if you did the upgrade while at WDW in August, it will expire in August because that is when you got the actual pass. If you did not do the upgrade at WDW until November, then there is an error.
It used to be that it did not activate until you actually used it to enter a park, but that rule was changed a number of years ago.