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- require 'socket'
- require 'openssl'
- require 'httparty'
-
- module CryptCheck
- module Tls
- class Server
- TCP_TIMEOUT = 10
- SSL_TIMEOUT = 2*TCP_TIMEOUT
-
- class TLSException < ::StandardError
- end
- class TLSNotAvailableException < TLSException
- def to_s
- 'TLS seems not supported on this server'
- end
- end
- class MethodNotAvailable < TLSException
- end
- class CipherNotAvailable < TLSException
- end
- class InappropriateFallback < TLSException
- end
- class Timeout < ::StandardError
- end
- class TLSTimeout < Timeout
- end
- class ConnectionError < ::StandardError
- end
-
- attr_reader :certs, :keys, :dh
-
- def initialize(hostname, family, ip, port)
- @hostname, @family, @ip, @port = hostname, family, ip, port
- @dh = []
-
- @name = "#@ip:#@port"
- @name += " [#@hostname]" if @hostname
-
- Logger.info { @name.colorize :blue }
-
- fetch_supported_methods
- fetch_supported_ciphers
- fetch_dh
- fetch_ciphers_preferences
- fetch_ecdsa_certs
- fetch_supported_curves
- fetch_curves_preference
-
- check_fallback_scsv
-
- verify_certs
- exit
- end
-
- def supported_method?(method)
- ssl_client method
- Logger.info { " Method #{method}" }
- true
- rescue TLSException
- Logger.debug { " Method #{method} : not supported" }
- false
- end
-
- def fetch_supported_methods
- Logger.info { '' }
- Logger.info { 'Supported methods' }
- @supported_methods = Method.select { |m| supported_method? m }
- end
-
- def supported_cipher?(method, cipher)
- connection = ssl_client method, cipher
- Logger.info { " Cipher #{cipher}" }
- dh = connection.tmp_key
- if dh
- Logger.info { " PFS : #{dh}" }
- end
- connection
- rescue TLSException
- Logger.debug { " Cipher #{cipher} : not supported" }
- nil
- end
-
- def fetch_supported_ciphers
- Logger.info { '' }
- Logger.info { 'Supported ciphers' }
- @supported_ciphers = @supported_methods.collect do |method|
- ciphers = Cipher[method].collect do |cipher|
- connection = supported_cipher? method, cipher
- next nil unless connection
- [cipher, connection]
- end.compact.to_h
- [method, ciphers]
- end.to_h
- end
-
- def fetch_ciphers_preferences
- Logger.info { '' }
- Logger.info { 'Cipher suite preferences' }
-
- @preferences = @supported_ciphers.collect do |method, ciphers|
- ciphers = ciphers.keys
- preferences = if ciphers.size < 2
- Logger.info { " #{method} : " + 'not applicable'.colorize(:unknown) }
- nil
- else
- a, b, _ = ciphers
- ab = ssl_client(method, [a, b]).cipher.first
- ba = ssl_client(method, [b, a]).cipher.first
- if ab != ba
- Logger.info { " #{method} : " + 'client preference'.colorize(:warning) }
- :client
- else
- sort = -> (a, b) do
- connection = ssl_client method, [a, b]
- cipher = connection.cipher.first
- cipher == a.name ? -1 : 1
- end
- preferences = ciphers.sort &sort
- Logger.info { " #{method} : " + preferences.collect { |c| c.to_s :short }.join(', ') }
- preferences
- end
- end
- [method, preferences]
- end.to_h
- end
-
- def fetch_dh
- @dh = @supported_ciphers.collect do |_, ciphers|
- ciphers.values.collect(&:tmp_key).select { |d| d.is_a? OpenSSL::PKey::DH }.collect &:size
- end.flatten
- end
-
- def fetch_ecdsa_certs
- @ecdsa_certs = {}
-
- @supported_ciphers.each do |method, ciphers|
- ecdsa = ciphers.keys.detect &:ecdsa?
- next unless ecdsa
-
- @ecdsa_certs = Curve.collect do |curve|
- begin
- connection = ssl_client method, ecdsa, curves: curve
- [curve, connection]
- rescue TLSException
- nil
- end
- end.compact.to_h
-
- break
- end
- end
-
- def fetch_supported_curves
- Logger.info { '' }
- Logger.info { 'Supported elliptic curves' }
- @supported_curves = []
-
- ecdsa_curve = @ecdsa_certs.keys.first
- if ecdsa_curve
- # If we have an ECDSA cipher, we need at least the certificate curve to do handshake,
- # but with lowest priority to check for ECHDE and not just ECDSA
-
- @supported_ciphers.each do |method, ciphers|
- ecdsa = ciphers.keys.detect &:ecdsa?
- next unless ecdsa
- @supported_curves = Curve.select do |curve|
- next true if curve == ecdsa_curve # ECDSA curve is always supported
- begin
- connection = ssl_client method, ecdsa, curves: [curve, ecdsa_curve]
- # Not too fast !!!
- # Handshake will **always** succeed, because ECDSA curve is always supported
- # So, need to test for the real curve
- dh = connection.tmp_key
- negociated_curve = dh.curve
- supported = negociated_curve != ecdsa_curve
- if supported
- Logger.info { " ECC curve #{curve}" }
- else
- Logger.debug { " ECC curve #{curve} : not supported" }
- end
- supported
- rescue TLSException
- false
- end
- end
- break
- end
- else
- # If we have no ECDSA ciphers, ECC supported are only ECDH ones
- # So peak an ECDH cipher and test all curves
- @supported_ciphers.each do |method, ciphers|
- ecdh = ciphers.keys.detect { |c| c.ecdh? or c.ecdhe? }
- next unless ecdh
- @supported_curves = Curve.select do |curve|
- begin
- ssl_client method, ecdh, curves: curve
- Logger.info { " ECC curve #{curve}" }
- true
- rescue TLSException
- Logger.debug { " ECC curve #{curve} : not supported" }
- false
- end
- end
- break
- end
- end
- end
-
- def fetch_curves_preference
- @curves_preference = if @supported_curves.size < 2
- Logger.info { 'Curves preference : ' + 'not applicable'.colorize(:unknown) }
- nil
- else
- method, cipher = @supported_ciphers.collect do |method, ciphers|
- cipher = ciphers.keys.detect { |c| c.ecdh? or c.ecdhe? }
- [method, cipher]
- end.detect { |n| !n.nil? }
-
- a, b, _ = @supported_curves
- ab, ba = [a, b], [b, a]
- if cipher.ecdsa?
- # In case of ECDSA, add the cert key at the end
- # Or no negociation possible
- ecdsa_curve = @ecdsa_certs.keys.first
- ab << ecdsa_curve
- ba << ecdsa_curve
- end
- ab = ssl_client(method, cipher, curves: ab).tmp_key.curve
- ba = ssl_client(method, cipher, curves: ba).tmp_key.curve
- if ab != ba
- Logger.info { 'Curves preference : ' + 'client preference'.colorize(:warning) }
- :client
- else
- sort = -> (a, b) do
- curves = [a, b]
- if cipher.ecdsa?
- # In case of ECDSA, add the cert key at the end
- # Or no negociation possible
- curves << ecdsa_curve
- end
- connection = ssl_client method, cipher, curves: curves
- curve = connection.tmp_key.curve
- curve == a.name ? -1 : 1
- end
- preferences = @supported_curves.sort &sort
- Logger.info { 'Curves preference : ' + preferences.collect { |c| c.to_s }.join(', ') }
- preferences
- end
- end
- end
-
- def check_fallback_scsv
- Logger.info { '' }
-
- @fallback_scsv = false
- if @supported_methods.size > 1
- # We will try to connect to the not better supported method
- method = @supported_methods[1]
-
- begin
- ssl_client method, fallback: true
- rescue InappropriateFallback
- @fallback_scsv = true
- end
- else
- @fallback_scsv = nil
- end
-
- text, color = case @fallback_scsv
- when true
- ['supported', :good]
- when false
- ['not supported', :error]
- when nil
- ['not applicable', :unknown]
- end
- Logger.info { 'Fallback SCSV : ' + text.colorize(color) }
- end
-
- Method.each do |method|
- method = method.name
- class_eval <<-RUBY_EVAL, __FILE__, __LINE__ + 1
- def #{method.to_s.downcase}?
- @supported_methods.detect { |m| m.name == method }
- end
- RUBY_EVAL
- end
-
- Cipher::TYPES.each do |type, _|
- class_eval <<-RUBY_EVAL, __FILE__, __LINE__ + 1
- def #{type}?
- @supported_ciphers.any? { |c| c.#{type}? }
- 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
-
- def tlsv1_2_only?
- tlsv1_2? and not ssl? and not tlsv1? and not tlsv1_1?
- end
-
- def pfs?
- supported_ciphers.any? { |c| c.pfs? }
- end
-
- def pfs_only?
- supported_ciphers.all? { |c| c.pfs? }
- end
-
- def ecdhe?
- supported_ciphers.any? { |c| c.ecdhe? }
- end
-
- def ecdhe_only?
- supported_ciphers.all? { |c| c.ecdhe? }
- end
-
- def aead?
- supported_ciphers.any? { |c| c.aead? }
- end
-
- def aead_only?
- supported_ciphers.all? { |c| c.aead? }
- end
-
- def sweet32?
- supported_ciphers.any? { |c| c.sweet32? }
- end
-
- def fallback_scsv?
- @fallback_scsv
- end
-
- def must_staple?
- @cert.extensions.any? { |e| e.oid == '1.3.6.1.5.5.7.1.24' }
- end
-
- private
- def connect(&block)
- socket = ::Socket.new @family, sock_type
- sockaddr = ::Socket.sockaddr_in @port, @ip
- #Logger.trace { "Connecting to #{@ip}:#{@port}" }
- begin
- status = socket.connect_nonblock sockaddr
- #Logger.trace { "Connecting to #{@ip}:#{@port} status : #{status}" }
- raise ConnectionError, status unless status == 0
- #Logger.trace { "Connected to #{@ip}:#{@port}" }
- block_given? ? block.call(socket) : nil
- rescue ::IO::WaitReadable
- #Logger.trace { "Waiting for read to #{@ip}:#{@port}" }
- raise Timeout, "Timeout when connect to #{@ip}:#{@port} (max #{TCP_TIMEOUT.humanize})" unless IO.select [socket], nil, nil, TCP_TIMEOUT
- retry
- rescue ::IO::WaitWritable
- #Logger.trace { "Waiting for write to #{@ip}:#{@port}" }
- raise Timeout, "Timeout when connect to #{@ip}:#{@port} (max #{TCP_TIMEOUT.humanize})" 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 if @hostname and method != :SSLv2
- #Logger.trace { "SSL connecting to #{name}" }
- begin
- ssl_socket.connect_nonblock
- #Logger.trace { "SSL connected to #{name}" }
- return block_given? ? block.call(ssl_socket) : nil
- rescue ::OpenSSL::SSL::SSLErrorWaitReadable
- #Logger.trace { "Waiting for SSL read to #{name}" }
- raise TLSTimeout, "Timeout when TLS connect to #{@ip}:#{@port} (max #{SSL_TIMEOUT.humanize})" unless IO.select [ssl_socket], nil, nil, SSL_TIMEOUT
- retry
- rescue ::OpenSSL::SSL::SSLErrorWaitWritable
- #Logger.trace { "Waiting for SSL write to #{name}" }
- raise TLSTimeout, "Timeout when TLS connect to #{@ip}:#{@port} (max #{SSL_TIMEOUT.humanize})" unless IO.select nil, [ssl_socket], nil, SSL_TIMEOUT
- retry
- rescue ::OpenSSL::SSL::SSLError => e
- case e.message
- when /state=SSLv2 read server hello A$/,
- /state=SSLv3 read server hello A$/,
- /state=SSLv3 read server hello A: wrong version number$/,
- /state=SSLv3 read server hello A: tlsv1 alert protocol version$/,
- /state=SSLv3 read server key exchange A: sslv3 alert handshake failure$/
- raise MethodNotAvailable, e
- when /state=SSLv2 read server hello A: peer error no cipher$/,
- /state=error: no ciphers available$/,
- /state=SSLv3 read server hello A: sslv3 alert handshake failure$/,
- /state=error: missing export tmp dh key$/
- raise CipherNotAvailable, e
- when /state=SSLv3 read server hello A: tlsv1 alert inappropriate fallback$/
- raise InappropriateFallback, e
- end
- raise
- rescue ::SystemCallError => e
- case e.message
- when /^Connection reset by peer - SSL_connect$/
- raise TLSNotAvailableException, e
- end
- raise
- ensure
- ssl_socket.close
- end
- end
-
- def ssl_client(method, ciphers = nil, curves: nil, fallback: false, &block)
- method = method.name
- ssl_context = ::OpenSSL::SSL::SSLContext.new method
- ssl_context.enable_fallback_scsv if fallback
-
- if ciphers
- ciphers = [ciphers] unless ciphers.is_a? Enumerable
- ciphers = ciphers.collect(&:name).join ':'
- else
- ciphers = Cipher::ALL
- end
- ssl_context.ciphers = ciphers
-
- if curves
- curves = [curves] unless curves.is_a? Enumerable
- # OpenSSL fails if the same curve is selected multiple times
- # So because Array#uniq preserves order, remove the less prefered ones
- curves = curves.collect(&:name).uniq.join ':'
- ssl_context.ecdh_curves = curves
- end
-
- Logger.trace { "Try method=#{method} / ciphers=#{ciphers} / curves=#{curves} / scsv=#{fallback}" }
- connect do |socket|
- ssl_connect socket, ssl_context, method do |ssl_socket|
- return block_given? ? block.call(ssl_socket) : ssl_socket
- end
- end
- end
-
- def verify_certs
- Logger.info { '' }
- Logger.info { 'Certificates' }
-
- # Let's begin the fun
- # First, collect "standard" connections
- # { method => { cipher => connection, ... }, ... }
- certs = @supported_ciphers.values.collect(&:values).flatten 1
- # Then, collect "ecdsa" connections
- # { curve => connection, ... }
- certs += @ecdsa_certs.values
- # For anonymous cipher, there is no certificate at all
- certs = certs.reject { |c| c.peer_cert.nil? }
- # Then, fetch cert
- certs = certs.collect { |c| Cert.new c }
- # Then, filter cert to keep uniq fingerprint
- @certs = certs.uniq { |c| c.fingerprint }
-
- @certs.each do |cert|
- key = cert.key
- identity = cert.valid?(@hostname || @ip)
- trust = cert.trusted?
- Logger.info { " Certificate #{cert.subject} [#{cert.serial}] issued by #{cert.issuer}" }
- Logger.info { ' Key : ' + Tls.key_to_s(key) }
- if identity
- Logger.info { ' Identity : ' + 'valid'.colorize(:good) }
- else
- Logger.info { ' Identity : ' + 'invalid'.colorize(:error) }
- end
- if trust == :trusted
- Logger.info { ' Trust : ' + 'trusted'.colorize(:good) }
- else
- Logger.info { ' Trust : ' + 'untrusted'.colorize(:error) + ' - ' + trust }
- end
- end
- @keys = @certs.collect &:key
- end
-
- def uniq_dh
- dh, find = [], []
- @dh.each do |k|
- f = [k.type, k.size]
- unless find.include? f
- dh << k
- find << f
- end
- end
- @dh = dh
- 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
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