An automated system for facilitating sales in dynamically-changing mobile retail environments includes a vendor/supplier connector module, a carrier connector module, a provisioning module, and a point-of-sale (POS) customization module. The vendor/supplier connector module facilitates automated exchange of product data with a plurality of different vendors or suppliers of products or services. The carrier connector module facilitates automated exchange of transportation data with a plurality of different carriers, with the transportation data corresponding to specific mobile retail environments. The provisioning module automatically determines, based on the product data and on the transportation data, products or services corresponding to a specific mobile retail environment. The POS customization module automatically generates re-configuration data for each of a plurality of POS interfaces. The re-configuration data limits each of the plurality of POS interfaces to facilitating sales of only the subset of the set of products or services that corresponds to a specific mobile retail environment.