An asset health monitoring system (AHMS) can assign a confidence indicator to some or all the services of a computing service provider. In response to drops in the confidence indicators, the AHMS can automatically initiate testing of services and/or computing assets associated with the services in order to raise confidence that a particular service and its computing assets will perform correctly. Further, the AHMS can automatically initiate remediation procedures for the particular service and/or specific computing assets that fail the confidence testing. By automatically triggering testing and/or remediation procedures, the AHMS can increase reliability of the computing service provider by preemptively identifying problems.