An encrypted session is established between a client device and a target server device when the client device initiates network connections through a proxy device. The client device initiates an encrypted session with the proxy device. Once the encrypted session is established, the client device communicates the address of the target server device to the proxy device. Then, the proxy device sends an encrypted session renegotiation message to the client device. The client device responds to the encrypted session renegotiation message by transmitting an encrypted session handshake message to the proxy device. The proxy device forwards the encrypted session handshake message to the target server device, and continues to forward handshake messages between the client device and the target server device, enabling the client device and the target server device to establish an encrypted session.