Context-based path selection for VPN clients to facilitate remote access to network-based applications

A server may receive, from a virtual private network (VPN) client of a client device, a message which indicates a request for a policy rule for communications with a network-based application (e.g. provided via a data center or cloud computing services). The server may obtain source attributes of the client device and a user thereof based on source identifiers, and destination attributes of the application based on a destination identifier, and select a policy rule associated with the attributes (e.g. indicative of security, risk, cost, load, and/or business function). The server may send a message which indicates a response and includes the policy rule for application at the VPN client. The policy rule may indicate a policy action for selecting a path, of a plurality of paths, identified by a path identifier, and specify conditions such as a location and/or a date, day, and/or time of the client device.