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copied!<p>I figured it out, thanks to that link to some decent documentation.</p> <p>For one thing, SSLSocket.connect() is only meant to be called on the client.</p> <p>But the main problem is that I'm trying to take a GServer socket and upgrade it to SSL. Instead, I should use OpenSSL::SSL::SSLServer.</p> <p>Also, I separated my certificate and private key into two files.</p> <p>Here is the working server:</p> <pre><code>#!/usr/bin/ruby require "socket" require "openssl" require "thread" listeningPort = Integer(ARGV[0]) server = TCPServer.new(listeningPort) sslContext = OpenSSL::SSL::SSLContext.new sslContext.cert = OpenSSL::X509::Certificate.new(File.open("cert.pem")) sslContext.key = OpenSSL::PKey::RSA.new(File.open("priv.pem")) sslServer = OpenSSL::SSL::SSLServer.new(server, sslContext) puts "Listening on port #{listeningPort}" loop do connection = sslServer.accept Thread.new { begin while (lineIn = connection.gets) lineIn = lineIn.chomp $stdout.puts "=> " + lineIn lineOut = "You said: " + lineIn $stdout.puts "<= " + lineOut connection.puts lineOut end rescue $stderr.puts $! end } end </code></pre> <p>And client:</p> <pre><code>#!/usr/bin/ruby require "socket" require "thread" require "openssl" host = ARGV[0] port = Integer(ARGV[1]) socket = TCPSocket.new(host, port) expectedCert = OpenSSL::X509::Certificate.new(File.open("cert.pem")) ssl = OpenSSL::SSL::SSLSocket.new(socket) ssl.sync_close = true ssl.connect if ssl.peer_cert.to_s != expectedCert.to_s stderrr.puts "Unexpected certificate" exit(1) end Thread.new { begin while lineIn = ssl.gets lineIn = lineIn.chomp $stdout.puts lineIn end rescue $stderr.puts "Error in input loop: " + $! end } while (lineOut = $stdin.gets) lineOut = lineOut.chomp ssl.puts lineOut end </code></pre>

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