The present invention provides for maintaining security context during a communication session between applications, without having to have executable code in either application for obtaining or generating a security context token (SCT) used to secure the communication. On a service side, a configuration file is provided that can be configured to indicate that automatic issuance of a SCT is enabled, thereby allowing a Web service engine to generate the SCT upon request. On the client side, when a message is sent from the client application to the service application, a policy engine accesses a policy that includes assertions indicating that a SCT is required for messages destined for the Web service application. As such, the policy engine requests and receives the SCT, which it uses to secure the message.