Powershell SSL Socket Client - ruby

Question

I am having issues using powershell to connect to an ssl socket with a self singed cert. I have a ruby client that connects fine, and I have also tested ncat with the --ssl switch and confirmed it connects just fine. $sslStream.AuthenticateAsClient is where the code fails and I get the following error from powershell "Exception calling "AuthenticateAsClient" with "1" argument(s): "A call to SSPI failed, see inner exception.". Any help is much appreciated.
Powershell Client
$socket = New-Object Net.Sockets.TcpClient('172.26.4.38', 8080)
$stream = $socket.GetStream()
$sslStream = New-Object System.Net.Security.SslStream($stream,$false,({$True} -as [Net.Security.RemoteCertificateValidationCallback]))
$sslStream.AuthenticateAsClient('172.26.4.38')
$writer = new-object System.IO.StreamWriter($sslStream)
$writer.WriteLine('hello world')
$writer.flush()
$socket.close()
Ruby Server
#!/usr/bin/env ruby
require 'openssl'
require 'socket'
tcp_server = TCPServer.new('172.26.4.38', 8080)
ctx = OpenSSL::SSL::SSLContext.new
ctx.ssl_version = :SSLv23
ctx.key = OpenSSL::PKey::RSA.new 2048
ctx.cert = OpenSSL::X509::Certificate.new
ctx.cert.subject = OpenSSL::X509::Name.new [['CN', '172.26.4.38']]
ctx.cert.issuer = ctx.cert.subject
ctx.cert.public_key = ctx.key
ctx.cert.not_before = Time.now
ctx.cert.not_after = Time.now + 60 * 60 * 24
ctx.cert.sign ctx.key, OpenSSL::Digest::SHA1.new
server = OpenSSL::SSL::SSLServer.new tcp_server, ctx
socket = server.accept
puts 'client connected'
puts socket.gets

Answer 1

This was an issue with the ruby code creating a self-sign cert. Using openssl and openssl req -x509 -nodes -days 365 -newkey rsa:2048 -keyout server.key -out server.crt the following powershell code worked correctly.
Client
$socket = New-Object Net.Sockets.TcpClient('172.26.4.38', 8080)
$stream = $socket.GetStream()
$sslStream = New-Object System.Net.Security.SslStream($stream,$false,({$True} -as [Net.Security.RemoteCertificateValidationCallback]))
$sslStream.AuthenticateAsClient('172.26.4.38')
$writer = new-object System. IO.StreamWriter($sslStream)
$writer.WriteLine('Hello World')
$writer.flush()
$socket.close()
Server
#!/usr/bin/env ruby
require 'openssl'
require 'socket'
tcp_server = TCPServer.new('172.26.4.38', 8080)
ctx = OpenSSL::SSL::SSLContext.new
ctx.cert = OpenSSL::X509::Certificate.new(File.open('server.crt'))
ctx.key = OpenSSL::PKey::RSA.new(File.open('server.key'))
server = OpenSSL::SSL::SSLServer.new tcp_server, ctx
socket = server.accept
puts 'client connected'
puts socket.gets

Answer 2

You can get powershell to ignore any cert issue by forcing the callback to just return true no matter what.
[Net.ServicePointManager]::ServerCertificateValidationCallback = {$true}
beaware that this will bypass any ssl validation in the powershell session.