I'm trying to write a generic server-client application that will be able to exchange data amongst servers. I've read over quite a few OpenSSL documents, and I have successfully setup my own CA and created a cert (and private key) for testing purposes. I'm stuck with Python 2.3, so I can't use the standard "ssl" library. Instead, I'm stuck with PyOpenSSL, which doesn't seem bad, but there aren't many documents out there about it. My question isn't really about getting it working. I'm more confused about the certificates and where they need to go. Here are my two programs that do work: Server: #!/bin/env python from OpenSSL import SSL import socket import pickle def verify_cb(conn, cert, errnum, depth, ok): print('Got cert: %s' % cert.get_subject()) return ok ctx = SSL.Context(SSL.TLSv1_METHOD) ctx.set_verify(SSL.VERIFY_PEER|SSL.VERIFY_FAIL_IF_NO_PEER_CERT, verify_cb) # ?????? ctx.use_privatekey_file('./Dmgr-key.pem') ctx.use_certificate_file('Dmgr-cert.pem') # ?????? ctx.load_verify_locations('./CAcert.pem') server = SSL.Connection(ctx, socket.socket(socket.AF_INET, socket.SOCK_STREAM)) server.bind(('', 50000)) server.listen(3) a, b = server.accept() c = a.recv(1024) print(c) Client: from OpenSSL import SSL import socket import pickle def verify_cb(conn, cert, errnum, depth, ok): print('Got cert: %s' % cert.get_subject()) return ok ctx = SSL.Context(SSL.TLSv1_METHOD) ctx.set_verify(SSL.VERIFY_PEER, verify_cb) # ?????????? ctx.use_privatekey_file('/home/justin/code/work/CA/private/Dmgr-key.pem') ctx.use_certificate_file('/home/justin/code/work/CA/Dmgr-cert.pem') # ????????? ctx.load_verify_locations('/home/justin/code/work/CA/CAcert.pem') sock = SSL.Connection(ctx, socket.socket(socket.AF_INET, socket.SOCK_STREAM)) sock.connect(('10.0.0.3', 50000)) a = Tester(2, 2) b = pickle.dumps(a) sock.send("Hello, world") sock.flush() sock.send(b) sock.shutdown() sock.close() I found this information from ftp://ftp.pbone.net/mirror/ftp.pld-linux.org/dists/2.0/PLD/i586/PLD/RPMS/python-pyOpenSSL-examples-0.6-2.i586.rpm which contains some example scripts. As you might gather, I don't fully understand the sections between the " # ????????." I don't get why the certificate and private key are needed on both the client and server. I'm not sure where each should go, but shouldn't I only need to distribute one part of the key (probably the public part)? It undermines the purpose of having asymmetric keys if you still need both on each server, right? I tried alternating removing either the pkey or cert on either box, and I get the following error no matter which I remove: OpenSSL.SSL.Error: [('SSL routines', 'SSL3_READ_BYTES', 'sslv3 alert handshake failure'), ('SSL routines', 'SSL3_WRITE_BYTES', 'ssl handshake failure')] Could someone explain if this is the expected behavior for SSL. Do I really need to distribute the private key and public cert to all my clients? I'm trying to avoid any huge security problems, and leaking private keys would tend to be a big one... Thanks for the help!