The present invention extends to methods, systems, and computer program products for automatically generating and refining health models. Embodiments of the invention use machine learning tools to analyze historical telemetry data from a server deployment. The tools output fingerprints, for example, small groupings of specific metrics-plus-behavioral parameters, that uniquely identify and describe past problem events mined from the historical data. Embodiments automatically translate the fingerprints into health models that can be directly applied to monitoring the running system. Fully-automated feedback loops for identifying past problems and giving advance notice as those problems emerge in the future is facilitated without any operator intervention. In some embodiments, a single portion of expert knowledge, for example, Key Performance Indicator (KPI) data, initiates health model generation. Once initiated, the feedback loop can be fully automated to access further telemetry and refine health models based on the further telemetry.