You wrote: The version of the modules I am using are Net::SSLeay '1.08' IO::Socket::SSL '0.96' These are fairly old versions (more than 4 years old). Please upgrade to newer versions. - IO::Socket::SSL is currently at 1.18 - Net::SSLeay is at 1.35 Both modules received large improvements in the last years. And why do you set SSL_startHandshake to 0? First this option isn't supported at all in version 0.96 of IO::Socket::SSL (please use the documentation coming with the version you use!), then it is documented for use with non-blocking sockets, where you want to call connect_SSL yourself. If it still doesn not work you can do the following: - enable debuging in IO::Socket::SSL ( use IO::Socket::SSL 'debug9' ) - use openssl s_client to connect to your server and see if it works - use openssl s_server to create another server and see if the client can connect to it