According to some embodiments, a bond is issued to an investor in exchange for value. The bond may be, for example, a tax-free municipal bond associated with (i) a spread to a pre-determined index, (ii) a nominal maturity date, (iii) an initial mandatory tender date prior to the nominal maturity date, and/or (iv) an option for the investor to extend the initial mandatory tender date during an initial decision period. According to some embodiments an indication is received, during the initial decision period, indicating that the investor will extend the initial mandatory tender date. It may then be arranged for the initial mandatory tender date to be extended such that the bond will be associated with a subsequent option for the investor to extend an extended tender date during a subsequent decision period.