Dynamically tailored trust for secure application-server networking and advanced enterprise security is provided. A system can individually assess the security posture of each application connecting to the Internet from each client device in an enterprise. For each application, the system tailors a security mode of the Internet connection based on the security posture of the application. Assessment of the security posture of an application is a comprehensive inventory of the security of the application, the security of the device hosting the application, the rights and security of the user, security attributes of the intended service or website being accessed, the security of the communication channel, and so forth. A network-based controller communicates with an agent running within a secure boot mode of each client device to select a security mode for application-service connection, including lean-trust direct access to the Internet, secure VPN-like access, or no access to the Internet.