Now I feel like I left money on the table. Last fall I was flying BOS-ORD and at the 24-hour mark I did OLCI. Upon checking in my companion and I (same PNR) were offered F buy-up's for $90/each. There were 5 seats for sale left and we bought 2. The next day we were checking our luggage and the TA tried to charge us $25/per bag. I told them we were in F and it should be free. The robotic TA, with very little care in the world, told us not sure what happened but we were in Y and to check with the GA. So we get to the gate and I tell them we were in F and the check-in desk said we were now in Y. She says "Ah, yes, we've been waiting for you Mr. xxxx. Unfortunately, we had to downgrade you because there are 2 seats in F out of order. However, we will give you and your companion $300/each and we've blocked out a whole row of MCE so it's just you and your companion. You'll also be refunded the $90/each upgrade fee. Why don't you wait to board last and we'll see if anyone doesn't show for F and we can get you on."

Unfortunately, everyone showed and I didn't have any status with AA at the time. BOS-ORD is only around 2-hours, so I just settled for their offer. When we boarded 6 E&F were empty and I presume the "inopp" seats.

I do wonder how we got chosen to be axed. As mentioned earlier there were 5 seats showing when the upgrade offer was taken. I know there's a possibility that perhaps other F passengers hadn't selected their seats. But it would seem that at least 1-2 more people after us were offered this upgrade offer, but we were the one's involunatrily downgraded.

Interesting to see a free upgrade netted you $500 at the gate, but a purchased upgrade only $300 for us.