A portable digital voice recorder is interfaced for data communication with a personal computer. The personal computer is connected by a data communication network with other devices such as other personal computers, a central dictation system, and/or a voice mail system. Voice data files previously generated by dictating information into the portable recorder are stored in the portable recorder and then uploaded to the personal computer. The voice data files include header data associated with the voice data files. The personal computer reads the header data and automatically forwards the voice data file to one or more of the other devices on the basis of information contained in the header data.