Billing Issues When Switching Memberships from Pay as you go to Monthly

The complaint is that when a member makes paid reservation with the free membership, then switched to a membership where that reservation would be free, the reservation still shows a charge.

We get a lot of complaints from members about courtreserve charging errors. For example, if someone is on a free pay as you go plan and they make a reservation in the future like 2 days out, their account will have a $15.83 charge on it. But, if they decide to switch to a monthly plan in the meanwhile, courtreserve does not automatically switch over all existing reservations in the next month to be covered in the monthly plan. Can you talk to the programmers about this or is there a toggle switch I can set to do this?