A method, client device and non-transitory computer readable storage medium for connecting to a virtual private network (VPN). A request to connect to a destination identified by a hostname is received from an application executed on the client device and a domain name system (DNS) lookup functionality is performed on the hostname, the DNS lookup functionality returning an address. It is then determined whether the returned address is a redirected address, whether a hypertext transmission protocol secure (HTTPS) probe configured for the hostname fails, or whether the returned address matches a cached route in which a transmission control protocol (TCP) connection establishment is unsuccessful. If any of the returned address is a redirected address, the HTTPS probe fails or the returned address matches the cached route and the TCP connection establishment is unsuccessful, the client device is connected to the VPN.