We are trying to connect to our server using boost asio and getting the error "handshake: sslv3 alert handshake failure". We have tried changing the ssl type, setting verify peer to none and a few other things with no success. The pem file we are using originated as a p12 file that we used openssl to output to a pem file for use in this project. Within the pem file there is both an encrypted private key and certificate. I have searched stackoverflow of a solution but the only similar thing that came up was openssl not being installed correctly which doesn't appear to be the problem in this case. Is there something I'm missing in my call back as I'm not passing a purpose or length, although I cannot find appropriate values to pass as purpose in the boost docs. - std::size_t max_length, // The maximum size for a password. - password_purpose purpose // Whether password is for reading or writing. using boost::asio::ip::tcp; boost::system::error_code ec; boost::asio::io_service io_service; boost::asio::ssl::context ctx(io_service, boost::asio::ssl::context::sslv23); ctx.set_password_callback(my_password_callback); ctx.use_private_key_file("/key1.pem",boost::asio::ssl::context_base::pem, ec); namespace ssl = boost::asio::ssl; typedef ssl::stream ssl_socket; ssl_socket sockconn(io_service, ctx); tcp::resolver resolver(io_service); tcp::resolver::query query(" tech.loopfish.com", "https"); boost::asio::connect(sockconn.lowest_layer(), resolver.resolve(query)); sockconn.lowest_layer().set_option(tcp::no_delay(true)); sockconn.set_verify_mode(boost::asio::ssl::verify_peer); sockconn.set_verify_callback(ssl::rfc2818_verification("tech.loopfish.com ")); sockconn.handshake(ssl_socket::client);