require 'socket' require 'openssl' require 'httparty' module CryptCheck module Tls class TlsNotSupportedServer attr_reader :hostname, :port def initialize(hostname, port) @hostname, @port = hostname, port end end class Server TCP_TIMEOUT = 10 SSL_TIMEOUT = 2*TCP_TIMEOUT EXISTING_METHODS = %i(TLSv1_2 TLSv1_1 TLSv1 SSLv3 SSLv2) SUPPORTED_METHODS = ::OpenSSL::SSL::SSLContext::METHODS class TLSException < ::Exception end class TLSNotAvailableException < TLSException end class CipherNotAvailable < TLSException end class Timeout < TLSException end class TLSTimeout < TLSException end class ConnectionError < TLSException end attr_reader :hostname, :port, :prefered_ciphers, :cert, :cert_valid, :cert_trusted def initialize(hostname, port) @log = Logging.logger[hostname] @hostname = hostname @port = port @log.error { "Begin analysis" } extract_cert #@prefered_ciphers = @supported_ciphers = Hash[SUPPORTED_METHODS.collect { |m| [m, []]}] fetch_prefered_ciphers check_supported_cipher @log.error { "End analysis" } end def supported_methods worst = EXISTING_METHODS.find { |method| !@prefered_ciphers[method].nil? } best = EXISTING_METHODS.reverse.find { |method| !@prefered_ciphers[method].nil? } { worst: worst, best: best } end def key key = @cert.public_key case key when ::OpenSSL::PKey::RSA then [:rsa, key.n.num_bits] when ::OpenSSL::PKey::DSA then [:dsa, key.p.num_bits] when ::OpenSSL::PKey::EC then [:ecc, key.group.degree] end end def key_size type, size = self.key if type == :ecc size = case size when 160 then 1024 when 224 then 2048 when 256 then 3072 when 384 then 7680 when 521 then 15360 end end size end def cipher_size cipher_strengths = supported_ciphers.collect { |c| c[2] }.uniq.sort worst, best = cipher_strengths.first, cipher_strengths.last { worst: worst, best: best } end EXISTING_METHODS.each do |method| class_eval <<-RUBY_EVAL, __FILE__, __LINE__ + 1 def #{method.to_s.downcase}? !prefered_ciphers[:#{method}].nil? end RUBY_EVAL end { md2: %w(md2WithRSAEncryption), md5: %w(md5WithRSAEncryption md5WithRSA), sha1: %w(sha1WithRSAEncryption sha1WithRSA dsaWithSHA1 dsaWithSHA1_2 ecdsa_with_SHA1) }.each do |name, signature| class_eval <<-RUBY_EVAL, __FILE__, __LINE__ + 1 def #{name}_sig? #{signature}.include? @cert.signature_algorithm end RUBY_EVAL end { md5: %w(MD5), sha1: %w(SHA), rc4: %w(RC4), des3: %w(3DES DES-CBC3), des: %w(DES-CBC) }.each do |name, ciphers| class_eval <<-RUBY_EVAL, __FILE__, __LINE__ + 1 def #{name}? supported_ciphers.any? { |supported| #{ciphers}.any? { |available| /(^|-)#\{available\}(-|$)/ =~ supported[0] } } end RUBY_EVAL end def ssl? sslv2? or sslv3? end def tls? tlsv1? or tlsv1_1? or tlsv1_2? end def tls_only? tls? and !ssl? end PFS_CIPHERS = [/^DHE-RSA-/, /^DHE-DSS-/, /^ECDHE-RSA-/, /^ECDHE-ECDSA-/] def pfs? supported_ciphers.any? { |cipher| PFS_CIPHERS.any? { |pc| pc =~ cipher[0] } } end def pfs_only? supported_ciphers.all? { |cipher| PFS_CIPHERS.any? { |pc| pc =~ cipher[0] } } end def supported_ciphers @supported_ciphers.values.flatten(1).uniq end def supported_ciphers_by_method @supported_ciphers end private def connect(family, host, port, &block) socket = ::Socket.new family, sock_type sockaddr = ::Socket.sockaddr_in port, host @log.debug { "Connecting to #{host}:#{port}" } begin status = socket.connect_nonblock sockaddr @log.debug { "Connecting to #{host}:#{port} status : #{status}" } raise ConnectionError, status unless status == 0 @log.debug { "Connected to #{host}:#{port}" } block_given? ? block.call(socket) : nil rescue ::IO::WaitReadable @log.debug { "Waiting for read to #{host}:#{port}" } raise Timeout unless IO.select [socket], nil, nil, TCP_TIMEOUT retry rescue ::IO::WaitWritable @log.debug { "Waiting for write to #{host}:#{port}" } raise Timeout unless IO.select nil, [socket], nil, TCP_TIMEOUT retry ensure socket.close end end def ssl_connect(socket, context, method, &block) ssl_socket = ::OpenSSL::SSL::SSLSocket.new socket, context ssl_socket.hostname = @hostname unless method == :SSLv2 @log.debug { "SSL connecting to #{@hostname}:#{@port}" } begin ssl_socket.connect_nonblock @log.debug { "SSL connected to #{@hostname}:#{@port}" } return block_given? ? block.call(ssl_socket) : nil rescue ::IO::WaitReadable @log.debug { "Waiting for SSL read to #{@hostname}:#{@port}" } raise TLSTimeout unless IO.select [socket], nil, nil, SSL_TIMEOUT retry rescue ::IO::WaitWritable @log.debug { "Waiting for SSL write to #{@hostname}:#{@port}" } raise TLSTimeout unless IO.select nil, [socket], nil, SSL_TIMEOUT retry rescue => e raise TLSException, e ensure ssl_socket.close end end def ssl_client(method, ciphers = nil, &block) ssl_context = ::OpenSSL::SSL::SSLContext.new method ssl_context.ciphers = ciphers if ciphers @log.debug { "Try #{method} connection with #{ciphers}" } [::Socket::AF_INET, ::Socket::AF_INET6].each do |family| @log.debug { "Try connection for family #{family}" } addrs = begin ::Socket.getaddrinfo @hostname, nil, family, :STREAM rescue ::SocketError => e @log.debug { "Unable to resolv #{@hostname} : #{e}" } next end addrs.each do |addr| connect family, addr[3], @port do |socket| ssl_connect socket, ssl_context, method do |ssl_socket| return block_given? ? block.call(ssl_socket) : nil end end end end @log.debug { "No SSL available on #{@hostname}" } raise CipherNotAvailable end def extract_cert EXISTING_METHODS.each do |method| next unless SUPPORTED_METHODS.include? method begin @cert, @chain = ssl_client(method) { |s| [s.peer_cert, s.peer_cert_chain] } @log.warn { "Certificate #{@cert.subject}" } break rescue TLSException => e @log.info { "Method #{method} not supported : #{e}" } end end raise TLSNotAvailableException unless @cert @cert_valid = ::OpenSSL::SSL.verify_certificate_identity @cert, @hostname @cert_trusted = verify_trust @chain, @cert end def prefered_cipher(method) cipher = ssl_client(method, %w(ALL:COMPLEMENTOFALL)) { |s| s.cipher } @log.warn { "Prefered cipher for #{method} : #{cipher[0]}" } cipher rescue Exception => e @log.info { "Method #{method} not supported : #{e}" } nil end def fetch_prefered_ciphers @prefered_ciphers = {} EXISTING_METHODS.each do |method| next unless SUPPORTED_METHODS.include? method @prefered_ciphers[method] = prefered_cipher method end raise TLSNotAvailableException.new unless @prefered_ciphers.any? { |_, c| !c.nil? } end def available_ciphers(method) ::OpenSSL::SSL::SSLContext.new(method).ciphers end def supported_cipher?(method, cipher) ssl_client method, [cipher] @log.warn { "Verify #{method} / #{cipher[0]} : OK" } true rescue TLSException => e @log.info { "Verify #{method} / #{cipher[0]} : NOK (#{e})" } false end def check_supported_cipher @supported_ciphers = {} EXISTING_METHODS.each do |method| next unless SUPPORTED_METHODS.include? method and @prefered_ciphers[method] @supported_ciphers[method] = available_ciphers(method).select { |cipher| supported_cipher? method, cipher } end end def verify_trust(chain, cert) store = ::OpenSSL::X509::Store.new store.purpose = OpenSSL::X509::PURPOSE_SSL_CLIENT store.set_default_paths %w(cacert).each do |directory| ::Dir.glob(::File.join '/usr/share/ca-certificates', directory, '*').each do |file| cert = ::OpenSSL::X509::Certificate.new ::File.read file begin store.add_cert cert rescue ::OpenSSL::X509::StoreError end end end chain.each do |cert| begin store.add_cert cert rescue ::OpenSSL::X509::StoreError end end trusted = store.verify cert p store.error_string unless trusted trusted end end class TcpServer < Server private def sock_type ::Socket::SOCK_STREAM end end class UdpServer < Server private def sock_type ::Socket::SOCK_DGRAM end end end end