Using SDK 2.2.0, I tried to connect to several different https servers, what I roughly observed is when the server is IIS, WICED module gives TLS handshake error but when the server is apache it connects. I couldnt have time to do detailed experiments but my initial impression there seems to be a compatibility issue when the TLS Server is Windows. WICED SDK only supports SSL3.0 and TLS1.1, by default IIS comes with SSL2.0 then someone can say this could be the problem. But we also tested with our windows server (IIS8.0) which is configured to SSL3.0. Is there someone having similar problems? I guess there should be a way to connect to a windows server using TLS.
Is your IIS server able to be reconfigured for TLS 1.0?