The present invention utilizes wireless communication paths between a PC (600) and a Personal Digital Assistant (PDA) (602) to synchronize data files between the PC and the PDA. Example wireless communication paths include a one; way paging network, a two-way paging network (152), a Cellular Digital Packet Data (CDPD) network, and a cordless telephone network. Automated updating of remote files is accomplished by invisibly updating using a paging or CDPD network, e.g., either after each change to the data file, after a series of changes to the data file, after exiting the scheduling application program, at predetermined intervals and/or even on-demand.; The invention provides a simple and efficient wireless way to synchronize data files on separate computers which do not require a fixed, direct connection to each other, such as a direct connection through the PSTN, infrared link, or wired or wireless LAN type connection. The synchronization of data files can be updated on a frequent, inconspicuous and convenient basis.