Abstract: Generally, this disclosure provides technology for authenticating a client device or a user thereof to an authentication agent that enforces authentication operations to a protected resource on the user's behalf with a contextually sensitive security procedure (CSSP). In some embodiments, the technology includes a client device having a multimode authentication module (MAM) thereon, which may function to determine which of a plurality of security policies in a CSSP is being enforced by an authentication agent with respect to a particular protected resource. Once the security policy is determined, the MAM may cause the authentication agent to perform authentication operations on the user's or client device's behalf, associated with the policy in a transparent or substantially transparent manner.