A segmentation server generates vulnerability exposure scores associated with workloads operating in a segmented computing environment. The segmentation server may automatically aggregate the vulnerability exposure scores in various ways to generate vulnerability exposure information representative of workloads in an administrative domain controlled by the segmentation server. The aggregated vulnerability exposure information may be presented in a manner that enables an administrator to easily evaluate different segmentation strategies and assess the risks associated with each of them. Moreover, the segmentation server can automatically generate a segmentation policy that modifies a configured segmentation strategy based on the vulnerability exposure scores to reduce exposure to certain vulnerabilities without impeding operation of the workloads.