net-ssh 7.3.2 → 8.0.0.beta3

data/lib/net/ssh/authentication/key_manager.rb

@@ -72,12 +72,16 @@ module Net
         def add(key_file)
           key_files.push(File.expand_path(key_file)).uniq!
           self
+        rescue ArgumentError
+          self
         end
 
         # Add the given keycert_file to the list of keycert files that will be used.
         def add_keycert(keycert_file)
           keycert_files.push(File.expand_path(keycert_file)).uniq!
           self
+        rescue ArgumentError
+          self
         end
 
         # Add the given keycert_data to the list of keycerts that will be used.
@@ -172,7 +176,11 @@ module Net
         def sign(identity, data, sig_alg = nil)
           info = known_identities[identity] or raise KeyManagerError, "the given identity is unknown to the key manager"
 
-          if info[:key].nil? && info[:from] == :file
+          if info[:from] == :pubkey_file_only
+            raise KeyManagerError, "the given identity is a public key only and cannot be used for signing without an agent"
+          end
+
+          if info[:key].nil? && (info[:from] == :file || info[:from] == :pubkey_file)
             begin
               info[:key] = KeyFactory.load_private_key(info[:file], options[:passphrase], !options[:non_interactive], options[:password_prompt])
             rescue OpenSSL::OpenSSLError, Exception => e
@@ -248,10 +256,14 @@ module Net
         def prepare_identities_from_files
           key_files.map do |file|
             if readable_file?(file)
-              identity = {}
+              identity = { privkey_file: file }
               cert_file = file + "-cert.pub"
               public_key_file = file + ".pub"
-              if readable_file?(cert_file)
+              if file.end_with?(".pub")
+                identity[:load_from] = :pubkey_file_only
+                identity[:pubkey_file] = file
+                identity.delete(:privkey_file)
+              elsif readable_file?(cert_file)
                 identity[:load_from] = :pubkey_file
                 identity[:pubkey_file] = cert_file
               elsif readable_file?(public_key_file)
@@ -260,7 +272,7 @@ module Net
               else
                 identity[:load_from] = :privkey_file
               end
-              identity.merge(privkey_file: file)
+              identity
             end
           end.compact
         end
@@ -282,7 +294,10 @@ module Net
             case identity[:load_from]
             when :pubkey_file
               key = KeyFactory.load_public_key(identity[:pubkey_file])
-              { public_key: key, from: :file, file: identity[:privkey_file] }
+              { public_key: key, from: :pubkey_file, file: identity[:privkey_file] }
+            when :pubkey_file_only
+              key = KeyFactory.load_public_key(identity[:pubkey_file])
+              { public_key: key, from: :pubkey_file_only, file: identity[:privkey_file] }
             when :privkey_file
               private_key = KeyFactory.load_private_key(
                 identity[:privkey_file], options[:passphrase], ask_passphrase, options[:password_prompt]
@@ -313,7 +328,7 @@ module Net
 
         def process_identity_loading_error(identity, e)
           case identity[:load_from]
-          when :pubkey_file
+          when :pubkey_file, :pubkey_file_only
             error { "could not load public key file `#{identity[:pubkey_file]}': #{e.class} (#{e.message})" }
           when :privkey_file
             error { "could not load private key file `#{identity[:privkey_file]}': #{e.class} (#{e.message})" }

data/lib/net/ssh/config.rb

@@ -229,7 +229,6 @@ module Net
           fingerprinthash: :fingerprint_hash,
           port: :port,
           user: :user,
-          userknownhostsfile: :user_known_hosts_file,
           checkhostip: :check_host_ip
         }.freeze
         def translate_config_key(hash, key, value, settings)
@@ -293,6 +292,8 @@ module Net
             hash[:set_env] = Shellwords.split(value.to_s).map { |e| e.split '=', 2 }.to_h
           when :numberofpasswordprompts
             hash[:number_of_password_prompts] = value.to_i
+          when :userknownhostsfile
+            hash[:user_known_hosts_file] = value.split(/\s+/)
           when *TRANSLATE_CONFIG_KEY_RENAME_MAP.keys
             hash[TRANSLATE_CONFIG_KEY_RENAME_MAP[key]] = value
           end

data/lib/net/ssh/known_hosts.rb

@@ -61,6 +61,37 @@ module Net
             false
           end
         end
+
+        # Returns true if the certificate lists no principals (unrestricted) or
+        # if the given hostname matches a listed principal. Host-certificate
+        # principals are shell-glob patterns, matching OpenSSH, whose
+        # sshkey_cert_check_host passes wildcard_pattern=1 so principals like
+        # "*.example.com" are matched with match_pattern rather than strcmp.
+        def matches_principal?(server_key, hostname)
+          server_key.valid_principals.empty? ||
+            server_key.valid_principals.any? { |principal| File.fnmatch(principal, hostname) }
+        end
+
+        # Returns true if the certificate's validity window covers the current time.
+        def matches_validity?(server_key)
+          return false if server_key.valid_after && server_key.valid_after > Time.now
+          return false if server_key.valid_before && server_key.valid_before < Time.now
+
+          true
+        end
+
+        # Returns true if the certificate is a host certificate. A user
+        # certificate (type :user) must never authenticate a host.
+        def matches_type?(server_key)
+          server_key.type == :host
+        end
+
+        # Returns true if every critical option in the certificate is one we can
+        # enforce. net-ssh enforces none, so any critical option is unsupported
+        # and, as OpenSSH does, must cause the certificate to be rejected.
+        def critical_options_supported?(server_key)
+          server_key.critical_options.empty?
+        end
       end
     end
 
@@ -89,6 +120,17 @@ module Net
       def empty?
         @host_keys.empty?
       end
+
+      # Returns the bare hostname, stripping port and IP portions from the
+      # comma-separated host string used internally.
+      #
+      # Examples:
+      #   "server.example.com"            => "server.example.com"
+      #   "server.example.com,1.2.3.4"    => "server.example.com"
+      #   "[server.example.com]:2222"      => "server.example.com"
+      def hostname
+        @host.split(",").first.gsub(/\[|\]:\d+/, "")
+      end
     end
 
     # Searches an OpenSSH-style known-host file for a given host, and returns all
@@ -160,6 +202,8 @@ module Net
       # file. The path is expanded file File.expand_path.
       def initialize(source)
         @source = File.expand_path(source)
+      rescue ArgumentError
+        @source = source
       end
 
       # Returns an array of all keys that are known to be associatd with the

data/lib/net/ssh/service/forward.rb

@@ -48,9 +48,9 @@ module Net
         # If three arguments are given, it is as if the local bind address is
         # "127.0.0.1", and the rest are applied as above.
         #
-        # To request an ephemeral port on the remote server, provide 0 (zero) for
-        # the port number. In all cases, this method will return the port that
-        # has been assigned.
+        # To request an ephemeral port on the local server, provide 0 (zero) for
+        # the local port number. In all cases, this method will return the port
+        # that has been assigned.
         #
         #   ssh.forward.local(1234, "www.capify.org", 80)
         #   assigned_port = ssh.forward.local("0.0.0.0", 0, "www.capify.org", 80)

data/lib/net/ssh/transport/chacha20_poly1305_cipher.rb

@@ -1,4 +1,4 @@
-require 'rbnacl'
+require 'openssl'
 require 'net/ssh/loggable'
 
 module Net
@@ -8,6 +8,15 @@ module Net
       class ChaCha20Poly1305Cipher
         include Net::SSH::Loggable
 
+        POLY1305_ALGORITHM = "POLY1305"
+        POLY1305_KEY_BYTES = 32
+        POLY1305_TAG_BYTES = 16
+        NAME = "chacha20-poly1305@openssh.com"
+        ZERO_BLOCK = "\x00".b * POLY1305_KEY_BYTES
+        ZERO_IV = "\x00".b * 16
+
+        class UnsupportedError < StandardError; end
+
         # Implicit HMAC, no need to do anything
         class ImplicitHMac
           def etm
@@ -24,7 +33,6 @@ module Net
           @chacha_hdr = OpenSSL::Cipher.new("chacha20")
           key_len = @chacha_hdr.key_len
           @chacha_main = OpenSSL::Cipher.new("chacha20")
-          @poly = RbNaCl::OneTimeAuths::Poly1305
           if key.size < key_len * 2
             error { "chacha20_poly1305: keylength doesn't match" }
             raise "chacha20_poly1305: keylength doesn't match"
@@ -43,9 +51,9 @@ module Net
         end
 
         def update_cipher_mac(payload, sequence_number)
-          iv_data = [0, 0, 0, sequence_number].pack("NNNN")
+          iv_data = packet_iv(sequence_number)
           @chacha_main.iv = iv_data
-          poly_key = @chacha_main.update(([0] * 32).pack('C32'))
+          poly_key = @chacha_main.update(ZERO_BLOCK)
 
           packet_length = payload.size
           length_data = [packet_length].pack("N")
@@ -57,35 +65,36 @@ module Net
           unencrypted_data = payload
           packet += @chacha_main.update(unencrypted_data)
 
-          packet += @poly.auth(poly_key, packet)
+          packet += self.class.poly1305_auth(poly_key, packet)
           return packet
         end
 
         def read_length(data, sequence_number)
-          iv_data = [0, 0, 0, sequence_number].pack("NNNN")
+          iv_data = packet_iv(sequence_number)
           @chacha_hdr.iv = iv_data
           @chacha_hdr.update(data).unpack1("N")
         end
 
         def read_and_mac(data, mac, sequence_number)
-          iv_data = [0, 0, 0, sequence_number].pack("NNNN")
+          iv_data = packet_iv(sequence_number)
           @chacha_main.iv = iv_data
-          poly_key = @chacha_main.update(([0] * 32).pack('C32'))
+          poly_key = @chacha_main.update(ZERO_BLOCK)
 
           iv_data[0] = 1.chr
           @chacha_main.iv = iv_data
           unencrypted_data = @chacha_main.update(data[4..])
-          begin
-            ok = @poly.verify(poly_key, mac, data[0..])
-            raise Net::SSH::Exception, "corrupted hmac detected #{name}" unless ok
-          rescue RbNaCl::BadAuthenticatorError
-            raise Net::SSH::Exception, "corrupted hmac detected #{name}"
-          end
+
+          expected_mac = self.class.poly1305_auth(poly_key, data[0..])
+          valid_mac = mac.respond_to?(:bytesize) &&
+                      mac.bytesize == POLY1305_TAG_BYTES &&
+                      OpenSSL.fixed_length_secure_compare(expected_mac, mac)
+          raise Net::SSH::Exception, "corrupted hmac detected #{name}" unless valid_mac
+
           return unencrypted_data
         end
 
         def mac_length
-          16
+          POLY1305_TAG_BYTES
         end
 
         def block_size
@@ -93,7 +102,7 @@ module Net
         end
 
         def name
-          "chacha20-poly1305@openssh.com"
+          NAME
         end
 
         def implicit_mac?
@@ -111,6 +120,70 @@ module Net
         def self.key_length
           64
         end
+
+        def self.iv_len
+          0
+        end
+
+        def self.auth_length
+          POLY1305_TAG_BYTES
+        end
+
+        def self.decrypt_private_key(ciphertext, auth_tag, key, _initialization_vector)
+          raise ArgumentError, "chacha20_poly1305: keylength doesn't match" unless
+            key.respond_to?(:bytesize) && key.bytesize == key_length
+
+          ciphertext = binary_string(ciphertext)
+          chacha = OpenSSL::Cipher.new("chacha20")
+          chacha.decrypt
+          chacha.key = binary_string(key[0...POLY1305_KEY_BYTES])
+
+          iv_data = ZERO_IV.dup
+          chacha.iv = iv_data
+          poly_key = chacha.update(ZERO_BLOCK)
+
+          valid_mac = OpenSSL.fixed_length_secure_compare(poly1305_auth(poly_key, ciphertext), auth_tag)
+          raise Net::SSH::Exception, "corrupted hmac detected #{NAME}" unless valid_mac
+
+          iv_data.setbyte(0, 1)
+          chacha.iv = iv_data
+          chacha.update(ciphertext)
+        end
+
+        def self.ensure_supported!
+          raise UnsupportedError, "OpenSSL::PKey raw private key APIs are unavailable" unless OpenSSL::PKey.respond_to?(:new_raw_private_key)
+
+          OpenSSL::Cipher.new("chacha20")
+
+          tag = poly1305_auth("\x00" * POLY1305_KEY_BYTES, "")
+          raise UnsupportedError, "OpenSSL Poly1305 authentication failed" unless tag.bytesize == POLY1305_TAG_BYTES
+        rescue OpenSSL::Cipher::CipherError, OpenSSL::PKey::PKeyError => e
+          raise UnsupportedError, e.message
+        end
+
+        def self.poly1305_auth(poly_key, data)
+          validate_poly1305_key!(poly_key)
+          OpenSSL::PKey.new_raw_private_key(POLY1305_ALGORITHM, binary_string(poly_key)).sign(nil, binary_string(data))
+        end
+
+        def self.validate_poly1305_key!(poly_key)
+          raise ArgumentError, "invalid Poly1305 key" unless poly_key.respond_to?(:bytesize) && poly_key.bytesize == POLY1305_KEY_BYTES
+        end
+
+        def self.binary_string(string)
+          string.dup.force_encoding('BINARY')
+        end
+        private_class_method :binary_string
+
+        def packet_iv(sequence_number)
+          iv_data = ZERO_IV.dup
+          iv_data.setbyte(12, (sequence_number >> 24) & 0xff)
+          iv_data.setbyte(13, (sequence_number >> 16) & 0xff)
+          iv_data.setbyte(14, (sequence_number >> 8) & 0xff)
+          iv_data.setbyte(15, sequence_number & 0xff)
+          iv_data
+        end
+        private :packet_iv
       end
     end
   end

data/lib/net/ssh/transport/chacha20_poly1305_cipher_loader.rb

@@ -1,15 +1,34 @@
 module Net
   module SSH
     module Transport
-      # Loads chacha20 poly1305 support which requires optinal dependency rbnacl
+      # Loads chacha20-poly1305 support backed by Ruby OpenSSL APIs.
       module ChaCha20Poly1305CipherLoader
         begin
           require 'net/ssh/transport/chacha20_poly1305_cipher'
+          Net::SSH::Transport::ChaCha20Poly1305Cipher.ensure_supported!
           LOADED = true
           ERROR = nil
         rescue LoadError => e
           ERROR = e
           LOADED = false
+        rescue StandardError => e
+          if defined?(Net::SSH::Transport::ChaCha20Poly1305Cipher::UnsupportedError) &&
+             e.is_a?(Net::SSH::Transport::ChaCha20Poly1305Cipher::UnsupportedError)
+            ERROR = e
+            LOADED = false
+          else
+            raise
+          end
+        end
+
+        def self.raiseUnlessLoaded(message)
+          description = LOADED ? '' : chacha20_poly1305_support_required
+          description += "#{ERROR.class} : \"#{ERROR.message}\"\n" if ERROR
+          raise NotImplementedError, "#{message}\n#{description}" unless LOADED
+        end
+
+        def self.chacha20_poly1305_support_required
+          "net-ssh requires openssl >= 3.2.0 and a crypto backend with ChaCha20 and Poly1305 enabled for chacha20-poly1305@openssh.com support.\n"
         end
       end
     end

data/lib/net/ssh/transport/cipher_factory.rb

@@ -100,7 +100,11 @@ module Net
         # if :iv_len option is supplied the third return value will be ivlen
         def self.get_lengths(name, options = {})
           klass = SSH_TO_CLASS[name]
-          return [klass.key_length, klass.block_size] unless klass.nil?
+          unless klass.nil?
+            result = [klass.key_length, klass.block_size]
+            result << klass.iv_len if options[:iv_len]
+            return result
+          end
 
           ossl_name = SSH_TO_OSSL[name]
           if ossl_name.nil? || ossl_name == "none"
@@ -124,6 +128,24 @@ module Net
           end
           result
         end
+
+        def self.auth_length(name)
+          klass = SSH_TO_CLASS[name]
+          return klass.auth_length if klass.respond_to?(:auth_length)
+
+          0
+        end
+
+        def self.decrypt_private_key(name, ciphertext, auth_tag, key, initialization_vector)
+          klass = SSH_TO_CLASS[name]
+          raise Net::SSH::Exception, "#{name} does not support private key decryption" unless
+            klass.respond_to?(:decrypt_private_key)
+
+          raise Net::SSH::Exception, "incorrect auth_tag length" unless
+            auth_tag.respond_to?(:bytesize) && auth_tag.bytesize == klass.auth_length
+
+          klass.decrypt_private_key(ciphertext, auth_tag, key, initialization_vector)
+        end
       end
     end
   end

data/lib/net/ssh/transport/gcm_cipher.rb

@@ -5,7 +5,11 @@ module Net
     module Transport
       ## Extension module for aes(128|256)gcm ciphers
       module GCMCipher
-        # rubocop:disable Metrics/AbcSize
+        BLOCK_SIZE = 16
+        IV_BYTES = 12
+        AUTH_TAG_BYTES = 16
+
+        # rubocop:disable Metrics/AbcSize, Metrics/MethodLength
         def self.extended(orig)
           # rubocop:disable Metrics/BlockLength
           orig.class_eval do
@@ -100,15 +104,32 @@ module Net
             end
 
             def mac_length
-              16
+              GCMCipher::AUTH_TAG_BYTES
             end
 
             def block_size
-              16
+              GCMCipher::BLOCK_SIZE
             end
 
             def self.block_size
-              16
+              GCMCipher::BLOCK_SIZE
+            end
+
+            def self.iv_len
+              GCMCipher::IV_BYTES
+            end
+
+            def self.auth_length
+              GCMCipher::AUTH_TAG_BYTES
+            end
+
+            def self.decrypt_private_key(ciphertext, auth_tag, key, initialization_vector)
+              cipher = new(encrypt: false, key: key)
+
+              cipher.nonce = initialization_vector
+              cipher.cipher.auth_tag = auth_tag.to_s
+              cipher.cipher.auth_data = ''
+              cipher.cipher.update(ciphertext.to_s) << cipher.cipher.final
             end
 
             #
@@ -117,7 +138,7 @@ module Net
             # N_MAX       maximum nonce (IV) length        12 octets
             #
             def iv_len
-              12
+              GCMCipher::IV_BYTES
             end
 
             #
@@ -201,7 +222,7 @@ module Net
         end
         # rubocop:enable Metrics/BlockLength
       end
-      # rubocop:enable Metrics/AbcSize
+      # rubocop:enable Metrics/AbcSize, Metrics/MethodLength
     end
   end
 end

data/lib/net/ssh/transport/kex/curve25519_sha256.rb

@@ -1,7 +1,4 @@
-gem 'x25519' # raise if the gem x25519 is not installed
-
-require 'x25519'
-
+require 'openssl'
 require 'net/ssh/transport/constants'
 require 'net/ssh/transport/kex/abstract5656'
 
@@ -12,25 +9,60 @@ module Net
         # A key-exchange service implementing the "curve25519-sha256@libssh.org"
         # key-exchange algorithm. (defined in https://tools.ietf.org/html/draft-ietf-curdle-ssh-curves-06)
         class Curve25519Sha256 < Abstract5656
+          ALGORITHM = "X25519"
+          KEY_BYTES = 32
+
+          class UnsupportedError < StandardError; end
+
+          def self.ensure_supported!
+            unless OpenSSL::PKey.respond_to?(:generate_key) && OpenSSL::PKey.respond_to?(:new_raw_public_key)
+              raise UnsupportedError, "OpenSSL::PKey raw public key APIs are unavailable"
+            end
+
+            key = generate_x25519_key
+            public_key = new_raw_public_key(key.raw_public_key)
+            validate_key_bytes!(key.derive(public_key), "shared secret", KEY_BYTES)
+          rescue OpenSSL::PKey::PKeyError => e
+            raise UnsupportedError, e.message
+          end
+
+          def self.generate_x25519_key
+            OpenSSL::PKey.generate_key(ALGORITHM)
+          end
+
+          def self.new_raw_public_key(key)
+            validate_key_bytes!(key, "public key", KEY_BYTES)
+            OpenSSL::PKey.new_raw_public_key(ALGORITHM, binary_string(key))
+          end
+
+          def self.validate_key_bytes!(key, label, expected_bytes)
+            raise ArgumentError, "invalid X25519 #{label}" unless key.respond_to?(:bytesize) && key.bytesize == expected_bytes
+          end
+
+          def self.binary_string(string)
+            string.dup.force_encoding('BINARY')
+          end
+          private_class_method :binary_string
+
           def digester
             OpenSSL::Digest::SHA256
           end
 
           private
 
-          def generate_key # :nodoc:
-            ::X25519::Scalar.generate
+          def generate_key
+            self.class.generate_x25519_key
           end
 
           ## string   Q_C, client's ephemeral public key octet string
           def ecdh_public_key_bytes
-            ecdh.public_key.to_bytes
+            ecdh.raw_public_key
           end
 
           # compute shared secret from server's public key and client's private key
           def compute_shared_secret(server_ecdh_pubkey)
-            pk = ::X25519::MontgomeryU.new(server_ecdh_pubkey)
-            OpenSSL::BN.new(ecdh.diffie_hellman(pk).to_bytes, 2)
+            pk = self.class.new_raw_public_key(server_ecdh_pubkey)
+            OpenSSL::BN.new(ecdh.derive(pk), 2)
           end
         end
       end

data/lib/net/ssh/transport/kex/curve25519_sha256_loader.rb

@@ -2,26 +2,34 @@ module Net
   module SSH
     module Transport
       module Kex
-        # Loads Curve25519Sha256 support which requires optinal dependencies
+        # Loads Curve25519Sha256 support backed by Ruby OpenSSL X25519 APIs.
         module Curve25519Sha256Loader
           begin
             require 'net/ssh/transport/kex/curve25519_sha256'
+            Net::SSH::Transport::Kex::Curve25519Sha256.ensure_supported!
             LOADED = true
             ERROR = nil
           rescue LoadError => e
             ERROR = e
             LOADED = false
+          rescue StandardError => e
+            if defined?(Net::SSH::Transport::Kex::Curve25519Sha256::UnsupportedError) &&
+               e.is_a?(Net::SSH::Transport::Kex::Curve25519Sha256::UnsupportedError)
+              ERROR = e
+              LOADED = false
+            else
+              raise
+            end
           end
 
           def self.raiseUnlessLoaded(message)
-            description = ERROR.is_a?(LoadError) ? dependenciesRequiredForX25519 : ''
-            description << "#{ERROR.class} : \"#{ERROR.message}\"\n" if ERROR
+            description = LOADED ? '' : x25519SupportRequired
+            description += "#{ERROR.class} : \"#{ERROR.message}\"\n" if ERROR
             raise NotImplementedError, "#{message}\n#{description}" unless LOADED
           end
 
-          def self.dependenciesRequiredForX25519
-            result = "net-ssh requires the following gems for x25519 support:\n"
-            result << " * x25519\n"
+          def self.x25519SupportRequired
+            "net-ssh requires openssl >= 3.2.0 and a crypto backend with X25519 enabled for curve25519-sha256 support.\n"
           end
         end
       end

data/lib/net/ssh/verifiers/always.rb

@@ -19,10 +19,8 @@ module Net
           # We've never seen this host before, so raise an exception.
           process_cache_miss(host_keys, arguments, HostKeyUnknown, "is unknown") if host_keys.empty?
 
-          # If we found any matches, check to see that the key type and
-          # blob also match.
-
-          found = host_keys.any? do |key|
+          # Find the known-hosts entry whose key matches the presented certificate.
+          found_key = host_keys.find do |key|
             if key.respond_to?(:matches_key?)
               key.matches_key?(arguments[:key])
             else
@@ -30,11 +28,17 @@ module Net
             end
           end
 
-          # If a match was found, return true. Otherwise, raise an exception
-          # indicating that the key was not recognized.
-          process_cache_miss(host_keys, arguments, HostKeyMismatch, "does not match") unless found
+          # No matching entry found — key is not recognized.
+          process_cache_miss(host_keys, arguments, HostKeyMismatch, "does not match") unless found_key
+
+          # For @cert-authority entries, enforce the certificate constraints
+          # OpenSSH checks in sshkey_cert_check_authority. A certificate signed by
+          # the trusted CA but failing any of these is rejected with
+          # HostKeyMismatch (not HostKeyUnknown) so AcceptNew does not swallow the
+          # failure and remember the rejected certificate.
+          verify_certificate!(found_key, host_keys, arguments)
 
-          found
+          true
         end
 
         def verify_signature(&block)
@@ -43,6 +47,37 @@ module Net
 
         private
 
+        # Enforces the @cert-authority certificate constraints for entries that
+        # implement them (Net::SSH::HostKeyEntries::CertAuthority). Non-certificate
+        # entries do not respond to these predicates and are left untouched.
+        def verify_certificate!(entry, host_keys, arguments)
+          cert = arguments[:key]
+
+          if entry.respond_to?(:matches_validity?) && !entry.matches_validity?(cert)
+            reason = if cert.valid_before && cert.valid_before < Time.now
+                       "Certificate has expired"
+                     else
+                       "Certificate is not yet valid"
+                     end
+            process_cache_miss(host_keys, arguments, HostKeyMismatch, reason)
+          end
+
+          if entry.respond_to?(:matches_principal?) && !entry.matches_principal?(cert, host_keys.hostname)
+            process_cache_miss(host_keys, arguments, HostKeyMismatch,
+                               "Certificate invalid: name is not a listed principal")
+          end
+
+          if entry.respond_to?(:matches_type?) && !entry.matches_type?(cert)
+            process_cache_miss(host_keys, arguments, HostKeyMismatch,
+                               "Certificate invalid: not a host certificate")
+          end
+
+          return unless entry.respond_to?(:critical_options_supported?) && !entry.critical_options_supported?(cert)
+
+          process_cache_miss(host_keys, arguments, HostKeyMismatch,
+                             "Certificate invalid: unsupported critical option")
+        end
+
         def process_cache_miss(host_keys, args, exc_class, message)
           exception = exc_class.new("fingerprint #{args[:fingerprint]} " +
                                     "#{message} for #{host_keys.host.inspect}")