All ESA transactions should be made at the time of the service for a given expense (ex. private school tuition, therapy, tutoring, etc). If a vendor/facility is requiring a pre-payment, it can only be for the current quarter. If you pre-pay for a service, it is likely that your expense report will be rejected and you may be at risk of having to pay back funds that were not charged within the current quarter. ESA account holders are advised not to pre-pay for services that are outside of the current quarter.