Abstract: A computer automatable system and method is provided for dynamically managing, calculating and tracking rolling payments (as opposed to installment payments) made by borrowers repaying their finance debt. Rolling payment is an enhanced repayment paradigm or method that flattens and adapts established periodic payments to match a borrower's repayment behavior by flexibly eliminating due dates with its related fixed payment amounts and, instead, enforces an agreed minimum rolling payment balance (RPB) that the borrower must maintain or exceed for the account to be current. To maintain the RPB above the agreed minimum, borrowers can repay any amount (irregular payment amounts) at anytime (irregular payment periods) and from anywhere. The embodied system and method dynamically adapts the payment posting frequency and repayment amount to match precisely the configured repayment objectives of the creditor, hence smoothing out the irregular payment amount and irregular payment period pattern.