Methods and systems for processing cryptographically secured connections by a gateway, between a client and a server, are performed. Upon receiving TCP and TLS/SSL handshakes associated with a client side connection, from a client (client computer) to the gateway, a probing connection is established. The probing connection completes the handshakes, and based on the completion of the handshakes, the gateway renders a decision, to bypass, block or inspect, the connections between the client and the server, allowing or not allowing data to pass through the connections between the client and the server.