A client computer requests a client-handheld conduit file from an installation server. The client computer then receives the client-handheld conduit file from the installation server and establishing a synchronization session between the client computer and a handheld computer coupled to the client computer. The client-handheld conduit file is then transmitted to the handheld computer from the client computer, and a client-handheld conduit opened between the client computer and the handheld computer using the client-handheld conduit file. A handheld file is subsequently requested from the installation server. The client computer receives the handheld file from the installation server, and transmits the handheld file from the client computer to the handheld computer for installation on the handheld computer. This entire method is performed each time a new handheld file is installed on the handheld computer. Also, all steps following the establishing step occur without any user intervention.