I agree the clock should have reset to Sept. when the AP was bought. I don't think they would allow it to be again upgraded to AP at this since those aren't available. Sorry you are caught up in this chaos.
YIkes, Disney is really starting to crack down of expiration of tickets. Let me see if I can write down what happened.
I bought 4 regular tickets from a reseller in April 2021
Annual passes went on sale so I upgraded all tickets Sept. 2021
3 of us went on our Oct trip. So 3 of our annual pass is Oct 2021 to Oct 2022
1 unused annual pass expiration ticket expires May 3, 2022.
All four of us going to Disney on May 28, 2022. Three of us have valid passes and was able to make park reservations. As a courtesy, the cast member made park reservations for the unused annual pass but before he enters into the park he has to go to Guest Relations to activate the pass. Since it will be technically expired, she said it is up to them on what to do. They might not honor the one year of use once he steps into the park. I told them that I would pay the difference in annual pass cost if that was the case. But since I originally purchased normal tickets and upgraded the AP that is why his expired in May 2022.
I told her that didn't make sense because my expire date was from Oct to Oct from when we entered the park. Lets say my husband went to Disney next week and activated his pass, it would be a year from that date. What comes into play, his ticket (AP) currently expires May 3 and we are not schedule to go until the end of the month and his ticket would technically be expired.
Cast member said it would be up to guest relations on how to handle it. She said it could be tied to our Oct date, he could get his year from when he entered or just be expired and not worth anything. She said it is not Disney fault that he did not go during that year. She said she has an AP and hasn't been since July. But the thing is, we bought a AP and haven't activated it yet so it should be good for the one year once it is activated.