Techniques are presented for seamless engagement and disengagement of Transport Layer Security proxy services. A first initial message of a 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 of the handshaking procedure is saved at the proxy device. A second initial message of a second 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. It is determined from the second handshaking procedure that inspection of the first secure communication session is not to be performed by the proxy device. The first secure communication session is established without examination of the communication traffic by the proxy device.