Based on an initiation request for a first connection from a Virtual Private Network (VPN) user device intended for a target, a second connection is established between a VPN concentrator and the VPN user device across a VPN tunnel and a third connection is established between the VPN concentrator and the target. The second connection is established with a first Maximum Segment Size (MSS) and the third connection is established with a second MSS. A first round trip time (RTT) for the second connection is measured. A second RTT for the third connection is measured. Parameters of at least one of the second connection or the third connection are optimized, where first parameters of the second connection are optimized based on the first RTT and second parameters of the third connection are optimized based on the second RTT.