A Point-of-Sale (POS) terminal in a retail environment is communicatively connected to one or more POS peripheral devices. Each POS peripheral device is associated with a configuration file that defines configuration settings for the POS peripheral device and environmental context information for the POS terminal and the POS controller. The configuration files are prioritized according to various criteria, and used to re-configure POS applications executing on the POS to operate optimally with the particular POS peripheral device. Additionally, the prioritized configuration files control the POS applications to update the configuration information.