It's crazy how difficult it is to bill things to prior months, and even the way the system works, our billing schedule is set from July to April (our tuition), but we have some fees that we collect in June, others that we don't collect until May, it's very difficult to do so with the current setup. We can't set up our billing to be June-June, because then if we want to automatically split the tuition, it will split between 13 months instead of 10. It would be easier if all families had all months available for billing, and you just choose the section that your tuition is billed during (like our July-April), for it to be split. Even though our tuition only covers 10 months, we still have fees that are billed outside that 10 month period.
Also, we recently enrolled some families on June 30, and it completely cut out July from their billing altogether, (even though the families were manually entered on June 28, and the billing due date wasn't until July 1... so why cut out 4 possible days of payment, as well as the fact that they might have already paid us manually and that's why we were setting up their account for htem), and made the billing only August-April, making each payment seem larger than it is supposed to be. Then I had to go into each one and refresh the payment plan while overriding late settings.
There should be an option to always override late settings or something like that, so this doesn't happen.