Question

I am just trying to get my head around SSL.

I have set up a Jetty server on my localhost, and generated my own certificate using Keytool.

Now when I go to https://localhost:8443/ I get the can’t trust this certificate error.

I use

keytool -export -alias pongus -keystore keystore -file certfile.cer

To create the certificate which I think is what the client needs to authenticate with the server. (This is where I could be very wrong!)

I have the following ruby code :

require 'net/https'
require 'openssl'

require 'open-uri'

puts 'yay' if File.exists?('certfile.cer')

uri = URI.parse("https://localhost:8443/")
http_session = Net::HTTP.new(uri.host, uri.port)
http_session.use_ssl = true
http_session.verify_mode = OpenSSL::SSL::VERIFY_PEER
http_session.ca_file = 'certfile.cer'
res = http_session.start do |http|
  # do some requests here
  http.get('/')
end

This does print ‘yay’, so the certfile.cer file does exist.

But I get the errors

/Applications/NetBeans/NetBeans 6.8.app/Contents/Resources/NetBeans/ruby2/jruby-1.4.0/lib/ruby/1.8/net/http.rb:586 warning: can't set verify locations
/Applications/NetBeans/NetBeans 6.8.app/Contents/Resources/NetBeans/ruby2/jruby-1.4.0/lib/ruby/1.8/net/http.rb:586:in `connect': certificate verify failed (OpenSSL::SSL::SSLError)

Any ideas what I am doing wrong?

EDIT

I want to get it so I guarantee that I am connecting to the right server, and the server can guarantee that it is me connecting to it, without any tampering in between. I am developing both the server and the client.

Answer 1

Your client needs access to its
private key.

You dont need the private key for server certificate verification. All you need is the certificate itself which contains the public key. Only the server has the private key. Well described here http://www.helpbytes.co.uk/https.php and here http://www.verisign.com/ssl/ssl-information-center/how-ssl-security-works/

My recommendation is simple. Check your certificate is correct.

openssl x509 -text -in mycert.crt

Also if you have access to the server you can explicitely validate if the certificate and key (used in httpd configuration) are correct (matches): http://kb.wisc.edu/middleware/page.php?id=4064 Please note this is explicit check ran on server. Never give out the private key. This check can be done only by the administrator to verify if the httpd was not misconfigured.

(openssl x509 -noout -modulus -in server.pem | openssl md5 ;\
   openssl rsa -noout -modulus -in server.key | openssl md5) | uniq

You can also debug the SSL certificate communication using standard openssl command. Issue this command then wait few seconds and then type QUIT and hit enter. You will see the certificate the server sends out.

openssl s_client -connect your.server.com:443

Also try to import the certificate to your browser and access the URL resource. Browser is able to validate it by clicking on https (Firefox and Chrome). Then you will see the certificate itself and validity information.

All the above was all about the server certificate. This is only one part of the problem. “I am connecting to the right server, and the server can guarantee that it is me connecting to it” Actully in your code above you only check for the server cert. Now. If you want a client certificate (the second part of your statement) than you need this in Ruby:

File.open( "client_certificate.pem", 'rb' ) { |f| cert = f.read }
File.open( "client_key.pem", 'rb' ) { |f| key = f.read }
http_session.cert = OpenSSL::X509::Certificate.new(cert)
http_session.key = OpenSSL::PKey::RSA.new(key, nil)

This is how client cert should be used in Ruby. If your private key is encrypted with a password just pass it instead nil in the second argument of RSA constructor.

I highly recommend to get server certificate working (your code) and then start with client certificate. Please note you keep your current code (ca_cert, validation constant) and add the above four lines to it.

Hope this helps.