Methods and systems for continuously and quantitatively assessing the risk to data confidentiality, integrity, and availability on identified on endpoints, servers, medical devices, and “Internet of things” devices in a networked healthcare environment monitor resource requests by user applications running on the various device. A map of resource usage by each application may be generated. Based on the map and a risk model (e.g., the contents of a risk database), application events associated with risks are detected and resources vulnerable to the risk may be identified.