A risk assessment system and method that calculates the risk of approving certain financial transactions, such as payment by check, and provides an indication as to whether to accept or decline the check. The system and method further include a process for calculating the risk of overturning the original decision whereby indications of whether to overturn a particular original transaction decline can be provided to a customer service agent such that the overturn decision is based upon the calculation of overturn risk using one or more overturn scoring modules.