Embodiments of the present invention address deficiencies of the art in respect to security enforcement point operability in a TLS secured communications path and provide a novel and non-obvious method, system and computer program product for the secure sharing of TLS session keys with trusted enforcement points. In one embodiment of the invention, a method for securely sharing TLS session keys with trusted enforcement points can be provided. The method can include conducting a TLS handshake with a TLS client to extract and decrypt a session key for a TLS session with the TLS client traversing at least one security enforcement point. The method further can include providing the session key to a communicatively coupled key server for distribution to the at least one security enforcement point. Finally, the method can include engaging in secure communications with the TLS client over the TLS session.