Techniques are presented herein for engagement and disengagement of Transport Layer Security proxy services with encrypted handshaking. In one embodiment, a first initial message of a first encrypted handshaking procedure for a first secure communication session between a first device and a second device is intercepted at a proxy device. The first initial message includes first key exchange information for encrypting the first encrypted handshaking procedure. A copy of the first initial message is stored at the proxy device. A second initial message of a second encrypted handshaking procedure for a second secure communication session between the proxy device and the second device is sent from the proxy device to the second device. The second initial message includes second key exchange information for encrypting the second encrypted handshaking procedure. The proxy device determines, based on the second encrypted handshaking procedure, whether to remain engaged or to disengage.