The techniques described herein enable the establishment of two simultaneous virtual private network (VPN) connections between a VPN gateway and a VPN client. The system is configured to update a routing table advertised to network resources when a VPN server instance fails and/or is taken offline. When a first VPN server instance fails and/or is taken offline, the first VPN server instance releases a claim of ownership on its range of IP addresses. After this release occurs, the second VPN server instance is configured to claim ownership of the range of IP addresses that used to be owned by the first VPN server instance. This updated claim of ownership is captured in an updated routing table that can then be advertised to the network resources. Consequently, the network resources use this updated routing table to correctly determine which VPN server instance to send data intended for the VPN client.