Abstract: A security gateway is provided to facilitate end-point compliance of connected clients to insure appropriate security levels are maintained. The gateway operates as a policy enforcement point, and, when necessary, is used to apply and/or provide the required level of compliance for a connection on behalf of a requesting client. In one aspect, a specified level of compliance for a given security feature is facilitated, even if the requesting client is not able to meet that level of compliance at the time of the request. An adaptive end-point compliance model measures the requesting client's current level of compliance for one or more software programs on the client and may either require remediation, for example, when knowing that the remediation server is available and responding, or may provide, via a surrogate connection, the necessary level of compliance when remediation is not possible.