The present invention uses a portable memory device to directly or wirelessly interact with one or more host computing devices to provide a customized configuration for one or more aspects associated with a computing session. In particular, software on the portable device will automatically execute on the host computing device after the host computing device recognizes the presence of the portable device. The software provides instructions for the host computing device to launch a select program on the host computing device and provide a customized configuration for the program. The customized configuration is based on information stored on the portable device. As such, the portable device may automatically set preferred interface or program configurations personalized to the user. For example, the interface settings for a desktop, productivity, or browser application may be tailored as defined by information stored on the portable device. Other settings, such as bookmarks for a browser, may be stored on the portable device and made available to the program launched on the host computing device.