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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 MethodNotAvailable < 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)
@hostname, @port = hostname, port
@dh = []
Logger.info { "#{hostname}:#{port}".colorize :blue }
extract_cert
Logger.info { '' }
Logger.info { "Key : #{Tls.key_to_s @cert.public_key}" }
fetch_prefered_ciphers
check_supported_cipher
end
def supported_methods
EXISTING_METHODS.select { |m| !@prefered_ciphers[m].nil? }
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
Tls::TYPES.each do |type, _|
class_eval <<-RUBY_EVAL, __FILE__, __LINE__ + 1
def #{type}?
supported_ciphers.any? { |s| Tls.#{type}? s.first }
end
RUBY_EVAL
end
def key_size
@cert.public_key.rsa_equivalent_size
end
def ssl?
sslv2? or sslv3?
end
def tls?
tlsv1? or tlsv1_1? or tlsv1_2?
end
def tls_only?
tls? and !ssl?
end
def pfs?
supported_ciphers.any? { |c| Tls.pfs? c.first }
end
def pfs_only?
supported_ciphers.all? { |c| Tls.pfs? c.first }
end
def supported_ciphers
@supported_ciphers.values.flatten(1).uniq
end
private
def connect(family, host, port, &block)
socket = ::Socket.new family, sock_type
sockaddr = ::Socket.sockaddr_in port, host
Logger.trace { "Connecting to #{host}:#{port}" }
begin
status = socket.connect_nonblock sockaddr
Logger.trace { "Connecting to #{host}:#{port} status : #{status}" }
raise ConnectionError, status unless status == 0
Logger.trace { "Connected to #{host}:#{port}" }
block_given? ? block.call(socket) : nil
rescue ::IO::WaitReadable
Logger.trace { "Waiting for read to #{host}:#{port}" }
raise Timeout unless IO.select [socket], nil, nil, TCP_TIMEOUT
retry
rescue ::IO::WaitWritable
Logger.trace { "Waiting for write to #{host}:#{port}" }
raise Timeout unless IO.select nil, [socket], nil, TCP_TIMEOUT
retry
rescue => e
case e.message
when /^Connection refused/
raise TLSNotAvailableException, e
end
raise
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
Logger.trace { "SSL connecting to #{@hostname}:#{@port}" }
begin
ssl_socket.connect_nonblock
Logger.trace { "SSL connected to #{@hostname}:#{@port}" }
return block_given? ? block.call(ssl_socket) : nil
rescue ::IO::WaitReadable
Logger.trace { "Waiting for SSL read to #{@hostname}:#{@port}" }
raise TLSTimeout unless IO.select [socket], nil, nil, SSL_TIMEOUT
retry
rescue ::IO::WaitWritable
Logger.trace { "Waiting for SSL write to #{@hostname}:#{@port}" }
raise TLSTimeout unless IO.select nil, [socket], nil, SSL_TIMEOUT
retry
rescue ::OpenSSL::SSL::SSLError => e
case e.message
when /state=SSLv2 read server hello A$/,
/state=SSLv3 read server hello A: wrong version number$/
raise MethodNotAvailable, e
when /state=error: no ciphers available$/,
/state=SSLv3 read server hello A: sslv3 alert handshake failure$/
raise CipherNotAvailable, e
end
raise TLSException, e
rescue => e
case e.message
when /^Connection reset by peer$/
raise MethodNotAvailable, e
end
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
Logger.trace { "Try #{method} connection with #{ciphers}" }
[::Socket::AF_INET, ::Socket::AF_INET6].each do |family|
Logger.trace { "Try connection for family #{family}" }
addrs = begin
::Socket.getaddrinfo @hostname, nil, family, :STREAM
rescue ::SocketError => e
Logger.error { "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
Logger.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] }
Logger.debug { "Certificate #{@cert.subject}" }
break
rescue TLSException
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, 'ALL:COMPLEMENTOFALL') { |s| s.cipher }
Logger.info { "Prefered cipher for #{Tls.colorize method} : #{Tls.colorize cipher.first}" }
cipher
rescue TLSException => e
Logger.debug { "Method #{Tls.colorize 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 unless @prefered_ciphers.any? { |_, c| !c.nil? }
end
def available_ciphers(method)
context = ::OpenSSL::SSL::SSLContext.new method
context.ciphers = 'ALL:COMPLEMENTOFALL'
context.ciphers
end
def supported_cipher?(method, cipher)
dh = ssl_client method, [cipher] { |s| s.tmp_key }
dh = dh ? " (#{'DH'.colorize :green} : #{Tls.key_to_s dh})" : ''
Logger.info { "#{Tls.colorize method} / #{Tls.colorize cipher[0]} : Supported#{dh}" }
true
rescue TLSException => e
Logger.debug { "#{Tls.colorize method} / #{Tls.colorize cipher[0]} : Not supported (#{e})" }
false
end
def check_supported_cipher
Logger.info { '' }
@supported_ciphers = {}
EXISTING_METHODS.each do |method|
next unless SUPPORTED_METHODS.include? method and @prefered_ciphers[method]
ciphers = available_ciphers(method).select { |cipher| supported_cipher? method, cipher }
@supported_ciphers[method] = ciphers
Logger.info { '' } unless ciphers.empty?
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