Since the 1980s classical music composition has become increasingly digital. The working papers of the American composer Steve Reich, housed at the Paul Sacher Stiftung (Basel, Switzerland), demonstrate one such changing trajectory. Reich began his professional career in the 1960s with pencil and paper, and moved into a digitally assisted compositional practice in the 1980s. After Reich’s adoption of the computer his working documents—in addition to handwritten sketchbooks and unbound sketches, audio tapes and assorted letters—become a blend of proprietary software files housed on 3.5” floppy disks and hand marked up computer print outs. While some of these digital documents still function due to backwards compatibility, not all of the software features are still supported and the surviving software disks run only on vintage hardware. This paper explores some of the challenges and additional information that these born-digital files offer the contemporary musicologist.