Create an Sinatra SSL Server

gen_keys.sh

# Generate a self-signed Certificate and a Private Key
openssl req -x509 -nodes -days 365 -newkey rsa:1024 -keyout pkey.pem -out cert.crt

server.rb

require 'sinatra'
require './sinatra_ssl'

set :ssl_certificate, "cert.crt"
set :ssl_key, "pkey.pem"
set :port, 9494

get '/try' do
    "helloworld"
end

sinatra_ssl.rb

require 'webrick/ssl'

module Sinatra
  class Application
    def self.run!
      certificate_content = File.open(ssl_certificate).read
      key_content = File.open(ssl_key).read

      server_options = {
        :Host => bind,
        :Port => port,
        :SSLEnable => true,
        :SSLCertificate => OpenSSL::X509::Certificate.new(certificate_content),
        # 123456 is the Private Key Password
        :SSLPrivateKey => OpenSSL::PKey::RSA.new(key_content,"123456")
      }

      Rack::Handler::WEBrick.run self, server_options do |server|
        [:INT, :TERM].each { |sig| trap(sig) { server.stop } }
        server.threaded = settings.threaded if server.respond_to? :threaded=
        set :running, true
      end
    end
  end
end

This is awesome and works great! Thank you!

For some reason I had to use require 'webrick/https' to get this to work or else I got SSL_ERROR_RX_RECORD_TOO_LONG. I am using Ruby 2.3 with bundler.

Looks nice. Is it possible to do it this way with Puma also?

This helped me along really well, thanks! FTR, I had to add in require 'webrick/https' to sinatra_ssl.rb before I could get it working.

require 'webrick/https' in sinatra_sll.rb solves the following problems:

wget https://localhost:9494/try --output-document=-   
--2018-03-29 12:41:37--  https://localhost:9494/try
Resolving localhost (localhost)... ::1, 127.0.0.1
Connecting to localhost (localhost)|::1|:9494... connected.
GnuTLS: An unexpected TLS packet was received.
Unable to establish SSL connection.

[2018-03-29 12:41:30] ERROR bad Request-Line `\x16\x03\x01\x00�\x01\x00\x00�\x03\x03Z��\x1D��������fⶂ���*�=P@=\x1A�LD�!�\x00\x00r�,��̩���'.
::1 - - [29/Mar/2018:12:41:30 CEST] "\x16\x03\x01\x00�\x01\x00\x00�\x03\x03Z��\x1D��������fⶂ���*�=P@=\x1A�LD�!�\x00\x00r�,��̩���" 400 335

I also tried:

openssl req -x509 -passout pass:"123456" -nodes -days 365 -newkey rsa:1024 -keyout pkey.pem -out cert.crt

having similar results.

Also:

wget --inet4-only https://127.0.0.1:9494/try --output-document=-  ; echo 
--2018-03-29 12:45:17--  https://127.0.0.1:9494/try
Connecting to 127.0.0.1:9494... connected.
GnuTLS: An unexpected TLS packet was received.
Unable to establish SSL connection.

Note still that:

wget http://127.0.0.1:9494/try --output-document=- -q  ; echo 
helloworld

openssl s_client -connect localhost:9494 -debug | grep Verifi

139755706946816:error:1408F10B:SSL routines:ssl3_get_record:wrong version number:../ssl/record/ssl3_record.c:252:
Verification: OK