TLS is a vital protocol used to secure communication over networks and it provides an end- to-end encrypted channel between two directly communicating parties. In certain situations it is not possible, or desirable, to establish direct connections from a client to a server, as for example when connecting to a server located on a secure network behind a gateway. In these cases chained connections are required. Mutual authentication and end-to-end encryption are important capabilities in a high assur- ance environment. These are provided by TLS, but there are no known solutions for chained connections. This thesis explores multiple methods that provides the functionality for chained connec- tions using TLS in a high assurance environment with trusted servers and a public key in- frastructure. A number of methods are formally described and analysed according to multi- ple criteria reflecting both functionality and security requirements. Furthermore, the most promising method is implemented and tested in order to verify that the method is viable in a real-life environment. The proposed solution modifies the TLS protocol through the use of an extension which allows for the distinction between direct and chained connections. The extension which also allows for specifying the structure of chained connections is used in the implementation of a method that creates chained connections by layering TLS connections inside each other. Testing demonstrates that the overhead of the method is negligible and that the method is a viable solution for creating chained connections with mutual authentication using TLS.