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require 'socket'
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require 'openssl'
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require 'httparty'
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module CryptCheck
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module Tls
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class Server
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TCP_TIMEOUT = 10
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SSL_TIMEOUT = 2*TCP_TIMEOUT
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class TLSException < ::StandardError
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end
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class TLSNotAvailableException < TLSException
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def to_s
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'TLS seems not supported on this server'
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end
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end
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class MethodNotAvailable < TLSException
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end
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class CipherNotAvailable < TLSException
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end
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class InappropriateFallback < TLSException
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end
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class Timeout < ::StandardError
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end
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class TLSTimeout < Timeout
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end
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class ConnectionError < ::StandardError
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end
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attr_reader :certs, :keys, :dh, :supported_curves
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def initialize(hostname, family, ip, port)
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@hostname, @family, @ip, @port = hostname, family, ip, port
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@dh = []
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@name = "#@ip:#@port"
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@name += " [#@hostname]" if @hostname
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Logger.info { @name.colorize :blue }
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fetch_supported_methods
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fetch_supported_ciphers
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fetch_dh
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fetch_ciphers_preferences
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fetch_ecdsa_certs
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fetch_supported_curves
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fetch_curves_preference
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check_fallback_scsv
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verify_certs
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end
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def supported_method?(method)
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ssl_client method
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Logger.info { " Method #{method}" }
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true
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rescue TLSException
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Logger.debug { " Method #{method} : not supported" }
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false
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end
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def fetch_supported_methods
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Logger.info { '' }
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Logger.info { 'Supported methods' }
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@supported_methods = Method.select { |m| supported_method? m }
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end
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def supported_cipher?(method, cipher)
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connection = ssl_client method, cipher
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Logger.info { " Cipher #{cipher}" }
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dh = connection.tmp_key
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if dh
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Logger.info { " PFS : #{dh}" }
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end
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connection
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rescue TLSException
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Logger.debug { " Cipher #{cipher} : not supported" }
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nil
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end
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def fetch_supported_ciphers
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Logger.info { '' }
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Logger.info { 'Supported ciphers' }
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@supported_ciphers = @supported_methods.collect do |method|
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ciphers = Cipher[method].collect do |cipher|
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connection = supported_cipher? method, cipher
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next nil unless connection
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[cipher, connection]
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end.compact.to_h
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[method, ciphers]
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end.to_h
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end
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def fetch_ciphers_preferences
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Logger.info { '' }
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Logger.info { 'Cipher suite preferences' }
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@preferences = @supported_ciphers.collect do |method, ciphers|
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ciphers = ciphers.keys
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preferences = if ciphers.size < 2
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Logger.info { " #{method} : " + 'not applicable'.colorize(:unknown) }
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nil
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else
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a, b, _ = ciphers
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ab = ssl_client(method, [a, b]).cipher.first
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ba = ssl_client(method, [b, a]).cipher.first
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if ab != ba
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Logger.info { " #{method} : " + 'client preference'.colorize(:warning) }
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:client
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else
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sort = -> (a, b) do
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connection = ssl_client method, [a, b]
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cipher = connection.cipher.first
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cipher == a.name ? -1 : 1
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end
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preferences = ciphers.sort &sort
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Logger.info { " #{method} : " + preferences.collect { |c| c.to_s :short }.join(', ') }
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preferences
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end
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end
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[method, preferences]
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end.to_h
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end
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def fetch_dh
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@dh = @supported_ciphers.collect do |_, ciphers|
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ciphers.values.collect(&:tmp_key).select { |d| d.is_a? OpenSSL::PKey::DH }.collect &:size
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end.flatten
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end
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def fetch_ecdsa_certs
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@ecdsa_certs = {}
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@supported_ciphers.each do |method, ciphers|
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ecdsa = ciphers.keys.detect &:ecdsa?
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next unless ecdsa
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@ecdsa_certs = Curve.collect do |curve|
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begin
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connection = ssl_client method, ecdsa, curves: curve
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[curve, connection]
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rescue TLSException
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nil
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end
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end.compact.to_h
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break
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end
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end
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def fetch_supported_curves
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Logger.info { '' }
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Logger.info { 'Supported elliptic curves' }
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@supported_curves = []
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ecdsa_curve = @ecdsa_certs.keys.first
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if ecdsa_curve
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# If we have an ECDSA cipher, we need at least the certificate curve to do handshake,
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# but with lowest priority to check for ECHDE and not just ECDSA
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@supported_ciphers.each do |method, ciphers|
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ecdsa = ciphers.keys.detect &:ecdsa?
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next unless ecdsa
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@supported_curves = Curve.select do |curve|
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next true if curve == ecdsa_curve # ECDSA curve is always supported
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begin
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connection = ssl_client method, ecdsa, curves: [curve, ecdsa_curve]
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# Not too fast !!!
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# Handshake will **always** succeed, because ECDSA
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# curve is always supported.
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# So, we need to test for the real curve!
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# Treaky case : if server preference is enforced,
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# ECDSA curve can be prefered over ECDHE one and so
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# really supported curve can be detected as not supported :(
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dh = connection.tmp_key
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negociated_curve = dh.curve
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supported = ecdsa_curve != negociated_curve
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if supported
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Logger.info { " ECC curve #{curve.name}" }
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else
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Logger.debug { " ECC curve #{curve.name} : not supported" }
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end
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supported
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rescue TLSException
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false
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end
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end
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break
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end
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else
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# If we have no ECDSA ciphers, ECC supported are only ECDH ones
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# So peak an ECDH cipher and test all curves
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@supported_ciphers.each do |method, ciphers|
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ecdh = ciphers.keys.detect { |c| c.ecdh? or c.ecdhe? }
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next unless ecdh
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@supported_curves = Curve.select do |curve|
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begin
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ssl_client method, ecdh, curves: curve
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Logger.info { " ECC curve #{curve}" }
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true
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rescue TLSException
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Logger.debug { " ECC curve #{curve} : not supported" }
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false
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end
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end
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break
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end
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end
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end
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def fetch_curves_preference
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@curves_preference = if @supported_curves.size < 2
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Logger.info { 'Curves preference : ' + 'not applicable'.colorize(:unknown) }
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nil
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else
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method, cipher = @supported_ciphers.collect do |method, ciphers|
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cipher = ciphers.keys.detect { |c| c.ecdh? or c.ecdhe? }
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[method, cipher]
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end.detect { |n| !n.nil? }
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a, b, _ = @supported_curves
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ab, ba = [a, b], [b, a]
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if cipher.ecdsa?
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# In case of ECDSA, add the cert key at the end
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# Or no negociation possible
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ecdsa_curve = @ecdsa_certs.keys.first
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ab << ecdsa_curve
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ba << ecdsa_curve
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end
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ab = ssl_client(method, cipher, curves: ab).tmp_key.curve
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ba = ssl_client(method, cipher, curves: ba).tmp_key.curve
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if ab != ba
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Logger.info { 'Curves preference : ' + 'client preference'.colorize(:warning) }
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:client
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else
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sort = -> (a, b) do
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curves = [a, b]
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if cipher.ecdsa?
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# In case of ECDSA, add the cert key at the end
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# Or no negociation possible
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curves << ecdsa_curve
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end
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connection = ssl_client method, cipher, curves: curves
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curve = connection.tmp_key.curve
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curve == a.name ? -1 : 1
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end
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preferences = @supported_curves.sort &sort
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Logger.info { 'Curves preference : ' + preferences.collect { |c| c.to_s }.join(', ') }
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preferences
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end
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end
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end
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def check_fallback_scsv
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Logger.info { '' }
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@fallback_scsv = false
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if @supported_methods.size > 1
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# We will try to connect to the not better supported method
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method = @supported_methods[1]
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begin
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ssl_client method, fallback: true
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rescue InappropriateFallback
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@fallback_scsv = true
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end
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else
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@fallback_scsv = nil
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end
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text, color = case @fallback_scsv
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when true
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['supported', :good]
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when false
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['not supported', :error]
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when nil
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['not applicable', :unknown]
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end
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Logger.info { 'Fallback SCSV : ' + text.colorize(color) }
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end
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Method.each do |method|
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method = method.name
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class_eval <<-RUBY_EVAL, __FILE__, __LINE__ + 1
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def #{method.to_s.downcase}?
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@supported_methods.detect { |m| m.name == method }
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end
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RUBY_EVAL
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end
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Cipher::TYPES.each do |type, _|
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class_eval <<-RUBY_EVAL, __FILE__, __LINE__ + 1
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def #{type}?
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@supported_ciphers.any? { |c| c.#{type}? }
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end
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RUBY_EVAL
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end
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def ssl?
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sslv2? or sslv3?
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end
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def tls?
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tlsv1? or tlsv1_1? or tlsv1_2?
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end
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def tls_only?
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tls? and !ssl?
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end
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def tlsv1_2_only?
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tlsv1_2? and not ssl? and not tlsv1? and not tlsv1_1?
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end
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def pfs?
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supported_ciphers.any? { |c| c.pfs? }
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end
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def pfs_only?
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supported_ciphers.all? { |c| c.pfs? }
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end
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def ecdhe?
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supported_ciphers.any? { |c| c.ecdhe? }
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end
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def ecdhe_only?
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supported_ciphers.all? { |c| c.ecdhe? }
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end
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def aead?
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supported_ciphers.any? { |c| c.aead? }
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end
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def aead_only?
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supported_ciphers.all? { |c| c.aead? }
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end
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def sweet32?
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supported_ciphers.any? { |c| c.sweet32? }
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end
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def fallback_scsv?
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@fallback_scsv
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end
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def must_staple?
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@cert.extensions.any? { |e| e.oid == '1.3.6.1.5.5.7.1.24' }
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end
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private
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def connect(&block)
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socket = ::Socket.new @family, sock_type
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sockaddr = ::Socket.sockaddr_in @port, @ip
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#Logger.trace { "Connecting to #{@ip}:#{@port}" }
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begin
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status = socket.connect_nonblock sockaddr
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#Logger.trace { "Connecting to #{@ip}:#{@port} status : #{status}" }
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raise ConnectionError, status unless status == 0
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|
#Logger.trace { "Connected to #{@ip}:#{@port}" }
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|
block_given? ? block.call(socket) : nil
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|
rescue ::IO::WaitReadable
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|
|
#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
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|
|
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
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|
|
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
|
|
|
|
|
|
Cert::SIGNATURE_ALGORITHMS.each do |s|
|
|
|
class_eval <<-RUBY_EVAL, __FILE__, __LINE__ + 1
|
|
|
def #{s}_sign?
|
|
|
@certs.any? &:#{s}?
|
|
|
end
|
|
|
RUBY_EVAL
|
|
|
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
|
|
|
|
