An example method of determining operational health of a virtualized computing system includes: monitoring, at a service executing in the virtualized computing system, a current configuration of a software-defined data center (SDDC) with respect to a desired state, the desired state including: a host cluster having hosts executing a virtualization layer thereon; a software-defined (SD) network deployed in the host cluster; shared storage accessible by the host cluster; a virtual infrastructure (VI) control plane managing the host cluster, the SD network, and the shared storage; and an orchestration control plane integrated with the virtualization layer and the VI control plane; determining a configuration status for the current configuration of the SDDC; monitoring, at the service, operational status of an application management system executing on the SDDC having the current configuration; and determining at least one measure of the operational health in response to the configuration status and the operational status.