Embodiments provide a system and method for stateless session synchronization between inspectors for high availability deployments. Man in the Middle inspectors of a communication session between a client and server exchange a shared key that is used as a common seed value in a mapping function algorithm. Each inspector generates identical key-pairs using the common mapping function algorithm, and the inspectors generate the session keys from the key-pairs. Inspectors use the session keys to decrypt and either actively or passively inspect data transferred in a session between a client and server.