At least one available wireless access point is identified at a particular location and a connection is established with the available wireless access point. Communication is attempted with a trusted endpoint over the wireless access point and the attempted communication with the trusted endpoint over the wireless access point is monitored to assess risk associated with the wireless access point. Results of the assessment, in some instances, can be reported to an access point risk manager and risk associated with future attempts to use the wireless access point can be assessed based at least in part on the reported assessment results.