a system for assisting a user with the proper printing of postage indicia and other value bearing items onto labels in rolls of labels in a label printer , and a roll for use therewith . the system includes providing a roll bearing pre - printed labels for printing with postage indicia . the roll has a plurality of label sets , each with a leader portion and a label body , where each leader has a serial number which is the same as a serial number located on its corresponding label body . interactive computer software guides a user to confirm that the serial number on the pre - printed label body to be printed with postage indicia matches a label serial number in the software that will be encoded into a 2 - d barcode portion of the postage indicia .