Abstract: Technologies are described herein for deploying an update to hosts in a heterogeneous host fleet. One or more relevant host attributes for hosts in the host fleet are identified. Hosts in the fleet of hosts are classified into groups based on the identified relevant host attributes. A pilot host set is built by selecting one or more hosts from one or more of the groups according to a pilot host selection criteria. The update is deployed to the hosts included in the pilot host set as a test deployment. If the test deployment is successful, the update is deployed to the remaining hosts in the fleet of hosts; otherwise, the deployment is modified to continue the deployment to a subset of the host or to cancel the deployment and to restore the hosts in the pilot host set to their previous states. An analysis may be conducted based on the deployment data to provide recommendations for future deployments.