Abstract: A system for dynamic authorization, entitlements, and conditional capabilities by operational context to authorize operating a vehicle in conjunction with a remote cloud unit is provided. The system includes a vehicle operational system providing a functional output and a computerized controller within the vehicle. The controller includes programming to collect data from a plurality of sources related to operation of the vehicle and provide the data to a plurality of operating context analyzers to generate an operating context. The controller further includes programming to receive an authorization to operate the vehicle operational system and selectively enable operation of the vehicle operational system based upon the authorization. The system further includes the plurality of operating context analyzers determining the operating context.