Sorry, looks like this was my fault. Looks like it is working as intended but I messed something on the server. Got to do some more testing though... @jmarcelino (btw, congrats for you position at pycom), Still you might wanne document the parameter server_hostname on the ussl.wrap_socket function. A just noticed that cert mismatch does not rise ussl.SSLError but OSError which is therefore wrong in the docs too.