A security server assigns users sessions to a provider that provides virtual private networks. The security server trains a machine-learned model to identify a provider from a set of providers. The security server obtains connection parameters associated with a requested VPN connection. Connection parameters comprise a location of a computing device that requested the VPN connection, a time of the requested VPN connection, a current and/or historical state of VPN performance data, and user preferences. The security server applies the machine-learned model to the connection parameters to identify a provider. The security server provisions a user session based on the provider and establishes a connection through the provider.