Secure authentication of a user on a host computer to a web server including a security device acquiring trust or a security context from the web server. The security device is operable of providing an X.509 certificate to a browser plug-in on the host computer. The browser plug-in on the host computer performing authentication of the security device and in response providing user credentials to the security device. The security device performing authentication of the user and requests a security context from the web server. In response, the web server provides a security context to the security device. The security device delegates the web server trust by transmitting the context to the host computer and enabling the user to securely access resources on the web server.