The invention relates to a network segmentation effectiveness attestation system and method. The method may comprise receiving a list of internet protocol (IP) addresses for information technology (IT) assets within a defined scope, and executing a plurality of segmentation scans from outside a cardholder data environment (CDE) using a plurality of software agents. The software agents may be deployed and orchestrated across multiple network tiers. The method may also comprise receiving, automatically interpreting, and certifying results from the segmentation scan, automatically generating a report from the results of the segmentation scan, and automatically posting the report for authorized users to access.