Methods and systems for monitoring use, determining risk, and alerting an operator of a vehicle having one or more autonomous (and/or semi-autonomous) operation features are provided. According to certain aspects, operating data from sensors within the vehicle may be used to determine risks associated with use of the features, which may include use at particular levels or with certain settings. The risk levels may be compared with warning thresholds to determine whether safe operation may be maintained under the operating conditions. When the risk levels exceed a threshold, a warning may be generated and presented to the vehicle operator, which may include information regarding the risks. The vehicle operator may then change the use levels or select an option to change the use levels of the features. The response of the vehicle operator may be used to determine or adjust aspects of an insurance policy associated with the vehicle.