My broker handles the calculations. In Quicken, I then enter a RtrnCap (to reduce the cost basis) and a MiscExp to convert the cash generated by the RtrnCap back to negative _IntIncTaxFree (as applicable). No version of Quicken will perform the calculation. I don't know of any software that does; maybe a high end investment management package. If you broker is not providing this data, I don't know how they can properly report your cap gains when you do close the holding via sale or call. Are they not showing a reduced cost basis with each interest payment received?