Disclosed are systems and methods of managing financial transactions such as the prepayments of loans. Various embodiments of the invention allow a lender to pay a prepayment credit to a borrower under certain conditions, and under other conditions for the borrower to pay a prepayment fee to the lender. Prepayment credits and fees may be calculated using various formulas that account for changes in a value of the debt and/or changes in financial conditions such as interest rates. Any prepayment fees may be subject to limitations configured to avoid settlement of debt for less than fair market value and to avoid undesirable accounting consequences associated with prepayment.