# frozen_string_literal: false require_relative "utils" if defined?(OpenSSL) class OpenSSL::TestSSL < OpenSSL::SSLTestCase def test_ctx_options ctx = OpenSSL::SSL::SSLContext.new assert (OpenSSL::SSL::OP_ALL & ctx.options) == OpenSSL::SSL::OP_ALL, "OP_ALL is set by default" ctx.options = 4 assert_equal 4, ctx.options & 4 if ctx.options != 4 pend "SSL_CTX_set_options() seems to be modified by distributor" end ctx.options = nil assert_equal OpenSSL::SSL::OP_ALL, ctx.options assert_equal true, ctx.setup assert_predicate ctx, :frozen? assert_equal nil, ctx.setup end def test_ssl_with_server_cert ctx_proc = -> ctx { ctx.cert = @svr_cert ctx.key = @svr_key ctx.extra_chain_cert = [@ca_cert] } server_proc = -> (ctx, ssl) { assert_equal @svr_cert.to_der, ssl.cert.to_der assert_equal nil, ssl.peer_cert readwrite_loop(ctx, ssl) } start_server(ctx_proc: ctx_proc, server_proc: server_proc) { |port| begin sock = TCPSocket.new("127.0.0.1", port) ctx = OpenSSL::SSL::SSLContext.new ssl = OpenSSL::SSL::SSLSocket.new(sock, ctx) ssl.connect assert_equal sock, ssl.io assert_equal nil, ssl.cert assert_equal @svr_cert.to_der, ssl.peer_cert.to_der assert_equal 2, ssl.peer_cert_chain.size assert_equal @svr_cert.to_der, ssl.peer_cert_chain[0].to_der assert_equal @ca_cert.to_der, ssl.peer_cert_chain[1].to_der ensure ssl&.close sock&.close end } end def test_sysread_and_syswrite start_server { |port| server_connect(port) { |ssl| str = "x" * 100 + "\n" ssl.syswrite(str) newstr = ssl.sysread(str.bytesize) assert_equal(str, newstr) buf = "" ssl.syswrite(str) assert_same buf, ssl.sysread(str.size, buf) assert_equal(str, buf) } } end def test_sync_close start_server { |port| begin sock = TCPSocket.new("127.0.0.1", port) ssl = OpenSSL::SSL::SSLSocket.new(sock) ssl.connect ssl.close assert_not_predicate sock, :closed? ensure sock&.close end begin sock = TCPSocket.new("127.0.0.1", port) ssl = OpenSSL::SSL::SSLSocket.new(sock) ssl.sync_close = true # !! ssl.connect ssl.close assert_predicate sock, :closed? ensure sock&.close end } end def test_copy_stream start_server do |port| server_connect(port) do |ssl| IO.pipe do |r, w| str = "hello world\n" w.write(str) IO.copy_stream(r, ssl, str.bytesize) IO.copy_stream(ssl, w, str.bytesize) assert_equal str, r.read(str.bytesize) end end end end def test_client_auth_failure vflag = OpenSSL::SSL::VERIFY_PEER|OpenSSL::SSL::VERIFY_FAIL_IF_NO_PEER_CERT start_server(verify_mode: vflag, ignore_listener_error: true) { |port| assert_handshake_error { server_connect(port) { |ssl| ssl.puts("abc"); ssl.gets } } } end def test_client_auth_success vflag = OpenSSL::SSL::VERIFY_PEER|OpenSSL::SSL::VERIFY_FAIL_IF_NO_PEER_CERT start_server(verify_mode: vflag) { |port| ctx = OpenSSL::SSL::SSLContext.new ctx.key = @cli_key ctx.cert = @cli_cert server_connect(port, ctx) { |ssl| ssl.puts("foo") assert_equal("foo\n", ssl.gets) } called = nil ctx = OpenSSL::SSL::SSLContext.new ctx.client_cert_cb = Proc.new{ |sslconn| called = true [@cli_cert, @cli_key] } server_connect(port, ctx) { |ssl| assert(called) ssl.puts("foo") assert_equal("foo\n", ssl.gets) } } end def test_client_auth_public_key vflag = OpenSSL::SSL::VERIFY_PEER|OpenSSL::SSL::VERIFY_FAIL_IF_NO_PEER_CERT start_server(verify_mode: vflag, ignore_listener_error: true) do |port| assert_raise(ArgumentError) { ctx = OpenSSL::SSL::SSLContext.new ctx.key = @cli_key.public_key ctx.cert = @cli_cert server_connect(port, ctx) { |ssl| ssl.puts("abc"); ssl.gets } } ctx = OpenSSL::SSL::SSLContext.new ctx.client_cert_cb = Proc.new{ |ssl| [@cli_cert, @cli_key.public_key] } assert_handshake_error { server_connect(port, ctx) { |ssl| ssl.puts("abc"); ssl.gets } } end end def test_client_ca ctx_proc = Proc.new do |ctx| ctx.client_ca = [@ca_cert] end vflag = OpenSSL::SSL::VERIFY_PEER|OpenSSL::SSL::VERIFY_FAIL_IF_NO_PEER_CERT start_server(verify_mode: vflag, ctx_proc: ctx_proc) { |port| ctx = OpenSSL::SSL::SSLContext.new client_ca_from_server = nil ctx.client_cert_cb = Proc.new do |sslconn| client_ca_from_server = sslconn.client_ca [@cli_cert, @cli_key] end server_connect(port, ctx) { |ssl| assert_equal([@ca], client_ca_from_server) } } end def test_read_nonblock_without_session EnvUtil.suppress_warning do start_server(start_immediately: false) { |port| sock = TCPSocket.new("127.0.0.1", port) ssl = OpenSSL::SSL::SSLSocket.new(sock) ssl.sync_close = true assert_equal :wait_readable, ssl.read_nonblock(100, exception: false) ssl.write("abc\n") IO.select [ssl] assert_equal('a', ssl.read_nonblock(1)) assert_equal("bc\n", ssl.read_nonblock(100)) assert_equal :wait_readable, ssl.read_nonblock(100, exception: false) ssl.close } end end def test_starttls server_proc = -> (ctx, ssl) { while line = ssl.gets if line =~ /^STARTTLS$/ ssl.write("x") ssl.flush ssl.accept break end ssl.write(line) end readwrite_loop(ctx, ssl) } EnvUtil.suppress_warning do # read/write on not started session start_server(start_immediately: false, server_proc: server_proc) { |port| begin sock = TCPSocket.new("127.0.0.1", port) ssl = OpenSSL::SSL::SSLSocket.new(sock) ssl.puts "plaintext" assert_equal "plaintext\n", ssl.gets ssl.puts("STARTTLS") ssl.read(1) ssl.connect ssl.puts "over-tls" assert_equal "over-tls\n", ssl.gets ensure ssl&.close sock&.close end } end end def test_parallel start_server { |port| ssls = [] 10.times{ sock = TCPSocket.new("127.0.0.1", port) ssl = OpenSSL::SSL::SSLSocket.new(sock) ssl.connect ssl.sync_close = true ssls << ssl } str = "x" * 1000 + "\n" ITERATIONS.times{ ssls.each{|ssl| ssl.puts(str) assert_equal(str, ssl.gets) } } ssls.each{|ssl| ssl.close } } end def test_verify_result start_server(ignore_listener_error: true) { |port| sock = TCPSocket.new("127.0.0.1", port) ctx = OpenSSL::SSL::SSLContext.new ctx.verify_mode = OpenSSL::SSL::VERIFY_PEER ssl = OpenSSL::SSL::SSLSocket.new(sock, ctx) ssl.sync_close = true begin assert_raise(OpenSSL::SSL::SSLError){ ssl.connect } assert_equal(OpenSSL::X509::V_ERR_SELF_SIGNED_CERT_IN_CHAIN, ssl.verify_result) ensure ssl.close end } start_server { |port| sock = TCPSocket.new("127.0.0.1", port) ctx = OpenSSL::SSL::SSLContext.new ctx.verify_mode = OpenSSL::SSL::VERIFY_PEER ctx.verify_callback = Proc.new do |preverify_ok, store_ctx| store_ctx.error = OpenSSL::X509::V_OK true end ssl = OpenSSL::SSL::SSLSocket.new(sock, ctx) ssl.sync_close = true begin ssl.connect assert_equal(OpenSSL::X509::V_OK, ssl.verify_result) ensure ssl.close end } start_server(ignore_listener_error: true) { |port| sock = TCPSocket.new("127.0.0.1", port) ctx = OpenSSL::SSL::SSLContext.new ctx.verify_mode = OpenSSL::SSL::VERIFY_PEER ctx.verify_callback = Proc.new do |preverify_ok, store_ctx| store_ctx.error = OpenSSL::X509::V_ERR_APPLICATION_VERIFICATION false end ssl = OpenSSL::SSL::SSLSocket.new(sock, ctx) ssl.sync_close = true begin assert_raise(OpenSSL::SSL::SSLError){ ssl.connect } assert_equal(OpenSSL::X509::V_ERR_APPLICATION_VERIFICATION, ssl.verify_result) ensure ssl.close end } end def test_exception_in_verify_callback_is_ignored start_server(ignore_listener_error: true) { |port| sock = TCPSocket.new("127.0.0.1", port) ctx = OpenSSL::SSL::SSLContext.new ctx.verify_mode = OpenSSL::SSL::VERIFY_PEER ctx.verify_callback = Proc.new do |preverify_ok, store_ctx| store_ctx.error = OpenSSL::X509::V_OK raise RuntimeError end ssl = OpenSSL::SSL::SSLSocket.new(sock, ctx) ssl.sync_close = true begin EnvUtil.suppress_warning do # SSLError, not RuntimeError assert_raise(OpenSSL::SSL::SSLError) { ssl.connect } end assert_equal(OpenSSL::X509::V_ERR_CERT_REJECTED, ssl.verify_result) ensure ssl.close end } end def test_sslctx_set_params ctx = OpenSSL::SSL::SSLContext.new ctx.set_params assert_equal OpenSSL::SSL::VERIFY_PEER, ctx.verify_mode ciphers_names = ctx.ciphers.collect{|v, _, _, _| v } assert ciphers_names.all?{|v| /A(EC)?DH/ !~ v }, "anon ciphers are disabled" assert ciphers_names.all?{|v| /(RC4|MD5|EXP|DES(?!-EDE|-CBC3))/ !~ v }, "weak ciphers are disabled" assert_equal 0, ctx.options & OpenSSL::SSL::OP_DONT_INSERT_EMPTY_FRAGMENTS assert_equal OpenSSL::SSL::OP_NO_COMPRESSION, ctx.options & OpenSSL::SSL::OP_NO_COMPRESSION end def test_post_connect_check_with_anon_ciphers pend "TLS 1.2 is not supported" unless tls12_supported? ctx_proc = -> ctx { ctx.ssl_version = :TLSv1_2 ctx.ciphers = "aNULL" ctx.security_level = 0 } start_server(ctx_proc: ctx_proc) { |port| ctx = OpenSSL::SSL::SSLContext.new ctx.ssl_version = :TLSv1_2 ctx.ciphers = "aNULL" ctx.security_level = 0 server_connect(port, ctx) { |ssl| assert_raise_with_message(OpenSSL::SSL::SSLError, /anonymous cipher suite/i) { ssl.post_connection_check("localhost.localdomain") } } } end def test_post_connection_check sslerr = OpenSSL::SSL::SSLError start_server { |port| server_connect(port) { |ssl| assert_raise(sslerr){ssl.post_connection_check("localhost.localdomain")} assert_raise(sslerr){ssl.post_connection_check("127.0.0.1")} assert(ssl.post_connection_check("localhost")) assert_raise(sslerr){ssl.post_connection_check("foo.example.com")} cert = ssl.peer_cert assert(!OpenSSL::SSL.verify_certificate_identity(cert, "localhost.localdomain")) assert(!OpenSSL::SSL.verify_certificate_identity(cert, "127.0.0.1")) assert(OpenSSL::SSL.verify_certificate_identity(cert, "localhost")) assert(!OpenSSL::SSL.verify_certificate_identity(cert, "foo.example.com")) } } exts = [ ["keyUsage","keyEncipherment,digitalSignature",true], ["subjectAltName","DNS:localhost.localdomain",false], ["subjectAltName","IP:127.0.0.1",false], ] @svr_cert = issue_cert(@svr, @svr_key, 4, exts, @ca_cert, @ca_key) start_server { |port| server_connect(port) { |ssl| assert(ssl.post_connection_check("localhost.localdomain")) assert(ssl.post_connection_check("127.0.0.1")) assert_raise(sslerr){ssl.post_connection_check("localhost")} assert_raise(sslerr){ssl.post_connection_check("foo.example.com")} cert = ssl.peer_cert assert(OpenSSL::SSL.verify_certificate_identity(cert, "localhost.localdomain")) assert(OpenSSL::SSL.verify_certificate_identity(cert, "127.0.0.1")) assert(!OpenSSL::SSL.verify_certificate_identity(cert, "localhost")) assert(!OpenSSL::SSL.verify_certificate_identity(cert, "foo.example.com")) } } exts = [ ["keyUsage","keyEncipherment,digitalSignature",true], ["subjectAltName","DNS:*.localdomain",false], ] @svr_cert = issue_cert(@svr, @svr_key, 5, exts, @ca_cert, @ca_key) start_server { |port| server_connect(port) { |ssl| assert(ssl.post_connection_check("localhost.localdomain")) assert_raise(sslerr){ssl.post_connection_check("127.0.0.1")} assert_raise(sslerr){ssl.post_connection_check("localhost")} assert_raise(sslerr){ssl.post_connection_check("foo.example.com")} cert = ssl.peer_cert assert(OpenSSL::SSL.verify_certificate_identity(cert, "localhost.localdomain")) assert(!OpenSSL::SSL.verify_certificate_identity(cert, "127.0.0.1")) assert(!OpenSSL::SSL.verify_certificate_identity(cert, "localhost")) assert(!OpenSSL::SSL.verify_certificate_identity(cert, "foo.example.com")) } } end def test_verify_certificate_identity [true, false].each do |criticality| cert = create_null_byte_SAN_certificate(criticality) assert_equal(false, OpenSSL::SSL.verify_certificate_identity(cert, 'www.example.com')) assert_equal(true, OpenSSL::SSL.verify_certificate_identity(cert, "www.example.com\0.evil.com")) assert_equal(false, OpenSSL::SSL.verify_certificate_identity(cert, '192.168.7.255')) assert_equal(true, OpenSSL::SSL.verify_certificate_identity(cert, '192.168.7.1')) assert_equal(false, OpenSSL::SSL.verify_certificate_identity(cert, '13::17')) assert_equal(true, OpenSSL::SSL.verify_certificate_identity(cert, '13:0:0:0:0:0:0:17')) end end def test_verify_hostname assert_equal(true, OpenSSL::SSL.verify_hostname("www.example.com", "*.example.com")) assert_equal(false, OpenSSL::SSL.verify_hostname("www.subdomain.example.com", "*.example.com")) end def test_verify_wildcard assert_equal(false, OpenSSL::SSL.verify_wildcard("foo", "x*")) assert_equal(true, OpenSSL::SSL.verify_wildcard("foo", "foo")) assert_equal(true, OpenSSL::SSL.verify_wildcard("foo", "f*")) assert_equal(true, OpenSSL::SSL.verify_wildcard("foo", "*")) assert_equal(false, OpenSSL::SSL.verify_wildcard("abc*bcd", "abcd")) assert_equal(false, OpenSSL::SSL.verify_wildcard("xn--qdk4b9b", "x*")) assert_equal(false, OpenSSL::SSL.verify_wildcard("xn--qdk4b9b", "*--qdk4b9b")) assert_equal(true, OpenSSL::SSL.verify_wildcard("xn--qdk4b9b", "xn--qdk4b9b")) end # Comments in this test is excerpted from http://tools.ietf.org/html/rfc6125#page-27 def test_post_connection_check_wildcard_san # case-insensitive ASCII comparison # RFC 6125, section 6.4.1 # # "..matching of the reference identifier against the presented identifier # is performed by comparing the set of domain name labels using a # case-insensitive ASCII comparison, as clarified by [DNS-CASE] (e.g., # "WWW.Example.Com" would be lower-cased to "www.example.com" for # comparison purposes) assert_equal(true, OpenSSL::SSL.verify_certificate_identity( create_cert_with_san('DNS:*.example.com'), 'www.example.com')) assert_equal(true, OpenSSL::SSL.verify_certificate_identity( create_cert_with_san('DNS:*.Example.COM'), 'www.example.com')) assert_equal(true, OpenSSL::SSL.verify_certificate_identity( create_cert_with_san('DNS:*.example.com'), 'WWW.Example.COM')) # 1. The client SHOULD NOT attempt to match a presented identifier in # which the wildcard character comprises a label other than the # left-most label (e.g., do not match bar.*.example.net). assert_equal(false, OpenSSL::SSL.verify_certificate_identity( create_cert_with_san('DNS:www.*.com'), 'www.example.com')) # 2. If the wildcard character is the only character of the left-most # label in the presented identifier, the client SHOULD NOT compare # against anything but the left-most label of the reference # identifier (e.g., *.example.com would match foo.example.com but # not bar.foo.example.com or example.com). assert_equal(true, OpenSSL::SSL.verify_certificate_identity( create_cert_with_san('DNS:*.example.com'), 'foo.example.com')) assert_equal(false, OpenSSL::SSL.verify_certificate_identity( create_cert_with_san('DNS:*.example.com'), 'bar.foo.example.com')) # 3. The client MAY match a presented identifier in which the wildcard # character is not the only character of the label (e.g., # baz*.example.net and *baz.example.net and b*z.example.net would # be taken to match baz1.example.net and foobaz.example.net and # buzz.example.net, respectively). ... assert_equal(true, OpenSSL::SSL.verify_certificate_identity( create_cert_with_san('DNS:baz*.example.com'), 'baz1.example.com')) assert_equal(true, OpenSSL::SSL.verify_certificate_identity( create_cert_with_san('DNS:*baz.example.com'), 'foobaz.example.com')) assert_equal(true, OpenSSL::SSL.verify_certificate_identity( create_cert_with_san('DNS:b*z.example.com'), 'buzz.example.com')) # Section 6.4.3 of RFC6125 states that client should NOT match identifier # where wildcard is other than left-most label. # # Also implicitly mentions the wildcard character only in singular form, # and discourages matching against more than one wildcard. # # See RFC 6125, section 7.2, subitem 2. assert_equal(false, OpenSSL::SSL.verify_certificate_identity( create_cert_with_san('DNS:*b*.example.com'), 'abc.example.com')) assert_equal(false, OpenSSL::SSL.verify_certificate_identity( create_cert_with_san('DNS:*b*.example.com'), 'ab.example.com')) assert_equal(false, OpenSSL::SSL.verify_certificate_identity( create_cert_with_san('DNS:*b*.example.com'), 'bc.example.com')) # ... However, the client SHOULD NOT # attempt to match a presented identifier where the wildcard # character is embedded within an A-label or U-label [IDNA-DEFS] of # an internationalized domain name [IDNA-PROTO]. assert_equal(true, OpenSSL::SSL.verify_certificate_identity( create_cert_with_san('DNS:xn*.example.com'), 'xn1ca.example.com')) # part of A-label assert_equal(false, OpenSSL::SSL.verify_certificate_identity( create_cert_with_san('DNS:xn--*.example.com'), 'xn--1ca.example.com')) # part of U-label # dNSName in RFC5280 is an IA5String so U-label should NOT be allowed # regardless of wildcard. # # See Section 7.2 of RFC 5280: # IA5String is limited to the set of ASCII characters. assert_equal(false, OpenSSL::SSL.verify_certificate_identity( create_cert_with_san('DNS:á*.example.com'), 'á1.example.com')) end def test_post_connection_check_wildcard_cn assert_equal(true, OpenSSL::SSL.verify_certificate_identity( create_cert_with_name('*.example.com'), 'www.example.com')) assert_equal(true, OpenSSL::SSL.verify_certificate_identity( create_cert_with_name('*.Example.COM'), 'www.example.com')) assert_equal(true, OpenSSL::SSL.verify_certificate_identity( create_cert_with_name('*.example.com'), 'WWW.Example.COM')) assert_equal(false, OpenSSL::SSL.verify_certificate_identity( create_cert_with_name('www.*.com'), 'www.example.com')) assert_equal(true, OpenSSL::SSL.verify_certificate_identity( create_cert_with_name('*.example.com'), 'foo.example.com')) assert_equal(false, OpenSSL::SSL.verify_certificate_identity( create_cert_with_name('*.example.com'), 'bar.foo.example.com')) assert_equal(true, OpenSSL::SSL.verify_certificate_identity( create_cert_with_name('baz*.example.com'), 'baz1.example.com')) assert_equal(true, OpenSSL::SSL.verify_certificate_identity( create_cert_with_name('*baz.example.com'), 'foobaz.example.com')) assert_equal(true, OpenSSL::SSL.verify_certificate_identity( create_cert_with_name('b*z.example.com'), 'buzz.example.com')) # Section 6.4.3 of RFC6125 states that client should NOT match identifier # where wildcard is other than left-most label. # # Also implicitly mentions the wildcard character only in singular form, # and discourages matching against more than one wildcard. # # See RFC 6125, section 7.2, subitem 2. assert_equal(false, OpenSSL::SSL.verify_certificate_identity( create_cert_with_name('*b*.example.com'), 'abc.example.com')) assert_equal(false, OpenSSL::SSL.verify_certificate_identity( create_cert_with_name('*b*.example.com'), 'ab.example.com')) assert_equal(false, OpenSSL::SSL.verify_certificate_identity( create_cert_with_name('*b*.example.com'), 'bc.example.com')) assert_equal(true, OpenSSL::SSL.verify_certificate_identity( create_cert_with_name('xn*.example.com'), 'xn1ca.example.com')) assert_equal(false, OpenSSL::SSL.verify_certificate_identity( create_cert_with_name('xn--*.example.com'), 'xn--1ca.example.com')) # part of U-label # Subject in RFC5280 states case-insensitive ASCII comparison. # # See Section 7.2 of RFC 5280: # IA5String is limited to the set of ASCII characters. assert_equal(false, OpenSSL::SSL.verify_certificate_identity( create_cert_with_name('á*.example.com'), 'á1.example.com')) end def create_cert_with_san(san) ef = OpenSSL::X509::ExtensionFactory.new cert = OpenSSL::X509::Certificate.new cert.subject = OpenSSL::X509::Name.parse("/DC=some/DC=site/CN=Some Site") ext = ef.create_ext('subjectAltName', san) cert.add_extension(ext) cert end def create_cert_with_name(name) cert = OpenSSL::X509::Certificate.new cert.subject = OpenSSL::X509::Name.new([['DC', 'some'], ['DC', 'site'], ['CN', name]]) cert end # Create NULL byte SAN certificate def create_null_byte_SAN_certificate(critical = false) ef = OpenSSL::X509::ExtensionFactory.new cert = OpenSSL::X509::Certificate.new cert.subject = OpenSSL::X509::Name.parse "/DC=some/DC=site/CN=Some Site" ext = ef.create_ext('subjectAltName', 'DNS:placeholder,IP:192.168.7.1,IP:13::17', critical) ext_asn1 = OpenSSL::ASN1.decode(ext.to_der) san_list_der = ext_asn1.value.reduce(nil) { |memo,val| val.tag == 4 ? val.value : memo } san_list_asn1 = OpenSSL::ASN1.decode(san_list_der) san_list_asn1.value[0].value = "www.example.com\0.evil.com" pos = critical ? 2 : 1 ext_asn1.value[pos].value = san_list_asn1.to_der real_ext = OpenSSL::X509::Extension.new ext_asn1 cert.add_extension(real_ext) cert end def socketpair if defined? UNIXSocket UNIXSocket.pair else Socket.pair(Socket::AF_INET, Socket::SOCK_STREAM, 0) end end def test_tlsext_hostname fooctx = OpenSSL::SSL::SSLContext.new fooctx.tmp_dh_callback = proc { Fixtures.pkey_dh("dh1024") } fooctx.cert = @cli_cert fooctx.key = @cli_key ctx_proc = proc { |ctx| ctx.servername_cb = proc { |ssl, servername| case servername when "foo.example.com" fooctx when "bar.example.com" nil else raise "unreachable" end } } start_server(ctx_proc: ctx_proc) do |port| sock = TCPSocket.new("127.0.0.1", port) begin ssl = OpenSSL::SSL::SSLSocket.new(sock) ssl.hostname = "foo.example.com" ssl.connect assert_equal @cli_cert.serial, ssl.peer_cert.serial assert_predicate fooctx, :frozen? ensure ssl&.close sock.close end sock = TCPSocket.new("127.0.0.1", port) begin ssl = OpenSSL::SSL::SSLSocket.new(sock) ssl.hostname = "bar.example.com" ssl.connect assert_equal @svr_cert.serial, ssl.peer_cert.serial ensure ssl&.close sock.close end end end def test_servername_cb_raises_an_exception_on_unknown_objects hostname = 'example.org' ctx2 = OpenSSL::SSL::SSLContext.new ctx2.cert = @svr_cert ctx2.key = @svr_key ctx2.tmp_dh_callback = proc { Fixtures.pkey_dh("dh1024") } ctx2.servername_cb = lambda { |args| Object.new } sock1, sock2 = socketpair s2 = OpenSSL::SSL::SSLSocket.new(sock2, ctx2) ctx1 = OpenSSL::SSL::SSLContext.new s1 = OpenSSL::SSL::SSLSocket.new(sock1, ctx1) s1.hostname = hostname t = Thread.new { assert_raise(OpenSSL::SSL::SSLError) do s1.connect end } assert_raise(ArgumentError) do s2.accept end assert t.join ensure sock1.close if sock1 sock2.close if sock2 end def test_verify_hostname_on_connect ctx_proc = proc { |ctx| exts = [ ["keyUsage", "keyEncipherment,digitalSignature", true], ["subjectAltName", "DNS:a.example.com,DNS:*.b.example.com," \ "DNS:c*.example.com,DNS:d.*.example.com"], ] ctx.cert = issue_cert(@svr, @svr_key, 4, exts, @ca_cert, @ca_key) ctx.key = @svr_key } start_server(ctx_proc: ctx_proc, ignore_listener_error: true) do |port| ctx = OpenSSL::SSL::SSLContext.new ctx.verify_hostname = true ctx.cert_store = OpenSSL::X509::Store.new ctx.cert_store.add_cert(@ca_cert) ctx.verify_mode = OpenSSL::SSL::VERIFY_PEER [ ["a.example.com", true], ["A.Example.Com", true], ["x.example.com", false], ["b.example.com", false], ["x.b.example.com", true], ["cx.example.com", true], ["d.x.example.com", false], ].each do |name, expected_ok| begin sock = TCPSocket.new("127.0.0.1", port) ssl = OpenSSL::SSL::SSLSocket.new(sock, ctx) ssl.hostname = name if expected_ok assert_nothing_raised { ssl.connect } else assert_handshake_error { ssl.connect } end ensure ssl.close if ssl sock.close if sock end end end end def test_connect_certificate_verify_failed_exception_message start_server(ignore_listener_error: true) { |port| ctx = OpenSSL::SSL::SSLContext.new ctx.set_params assert_raise_with_message(OpenSSL::SSL::SSLError, /self signed/) { server_connect(port, ctx) } } ctx_proc = proc { |ctx| ctx.cert = issue_cert(@svr, @svr_key, 30, [], @ca_cert, @ca_key, not_before: Time.now-100, not_after: Time.now-10) } start_server(ignore_listener_error: true, ctx_proc: ctx_proc) { |port| store = OpenSSL::X509::Store.new store.add_cert(@ca_cert) ctx = OpenSSL::SSL::SSLContext.new ctx.set_params(cert_store: store) assert_raise_with_message(OpenSSL::SSL::SSLError, /expired/) { server_connect(port, ctx) } } end def test_unset_OP_ALL ctx_proc = Proc.new { |ctx| # If OP_DONT_INSERT_EMPTY_FRAGMENTS is not defined, this test is # redundant because the default options already are equal to OP_ALL. # But it also degrades gracefully, so keep it ctx.options = OpenSSL::SSL::OP_ALL } start_server(ctx_proc: ctx_proc) { |port| server_connect(port) { |ssl| ssl.puts('hello') assert_equal("hello\n", ssl.gets) } } end def check_supported_protocol_versions possible_versions = [ OpenSSL::SSL::SSL3_VERSION, OpenSSL::SSL::TLS1_VERSION, OpenSSL::SSL::TLS1_1_VERSION, OpenSSL::SSL::TLS1_2_VERSION, # OpenSSL 1.1.1 defined?(OpenSSL::SSL::TLS1_3_VERSION) && OpenSSL::SSL::TLS1_3_VERSION, ].compact # Prepare for testing & do sanity check supported = [] possible_versions.each do |ver| catch(:unsupported) { ctx_proc = proc { |ctx| begin ctx.min_version = ctx.max_version = ver rescue ArgumentError, OpenSSL::SSL::SSLError throw :unsupported end } start_server(ctx_proc: ctx_proc, ignore_listener_error: true) do |port| begin server_connect(port) { } rescue OpenSSL::SSL::SSLError, Errno::ECONNRESET else supported << ver end end } end assert_not_empty supported supported end def test_set_params_min_version supported = check_supported_protocol_versions store = OpenSSL::X509::Store.new store.add_cert(@ca_cert) if supported.include?(OpenSSL::SSL::SSL3_VERSION) # SSLContext#set_params properly disables SSL 3.0 by default ctx_proc = proc { |ctx| ctx.min_version = ctx.max_version = OpenSSL::SSL::SSL3_VERSION } start_server(ctx_proc: ctx_proc, ignore_listener_error: true) { |port| ctx = OpenSSL::SSL::SSLContext.new ctx.set_params(cert_store: store, verify_hostname: false) assert_handshake_error { server_connect(port, ctx) { } } } end end def test_minmax_version supported = check_supported_protocol_versions # name: The string that would be returned by SSL_get_version() # method: The version-specific method name (if any) vmap = { OpenSSL::SSL::SSL3_VERSION => { name: "SSLv3", method: "SSLv3" }, OpenSSL::SSL::SSL3_VERSION => { name: "SSLv3", method: "SSLv3" }, OpenSSL::SSL::TLS1_VERSION => { name: "TLSv1", method: "TLSv1" }, OpenSSL::SSL::TLS1_1_VERSION => { name: "TLSv1.1", method: "TLSv1_1" }, OpenSSL::SSL::TLS1_2_VERSION => { name: "TLSv1.2", method: "TLSv1_2" }, # OpenSSL 1.1.1 defined?(OpenSSL::SSL::TLS1_3_VERSION) && OpenSSL::SSL::TLS1_3_VERSION => { name: "TLSv1.3", method: nil }, } # Server enables a single version supported.each do |ver| ctx_proc = proc { |ctx| ctx.min_version = ctx.max_version = ver } start_server(ctx_proc: ctx_proc, ignore_listener_error: true) { |port| supported.each do |cver| # Client enables a single version ctx1 = OpenSSL::SSL::SSLContext.new ctx1.min_version = ctx1.max_version = cver if ver == cver server_connect(port, ctx1) { |ssl| assert_equal vmap[cver][:name], ssl.ssl_version } else assert_handshake_error { server_connect(port, ctx1) { } } end # There is no version-specific SSL methods for TLS 1.3 if cver <= OpenSSL::SSL::TLS1_2_VERSION # Client enables a single version using #ssl_version= ctx2 = OpenSSL::SSL::SSLContext.new ctx2.ssl_version = vmap[cver][:method] if ver == cver server_connect(port, ctx2) { |ssl| assert_equal vmap[cver][:name], ssl.ssl_version } else assert_handshake_error { server_connect(port, ctx2) { } } end end end # Client enables all supported versions ctx3 = OpenSSL::SSL::SSLContext.new ctx3.min_version = ctx3.max_version = nil server_connect(port, ctx3) { |ssl| assert_equal vmap[ver][:name], ssl.ssl_version } } end if supported.size == 1 pend "More than one protocol version must be supported" end # Server sets min_version (earliest is disabled) sver = supported[1] ctx_proc = proc { |ctx| ctx.min_version = sver } start_server(ctx_proc: ctx_proc, ignore_listener_error: true) { |port| supported.each do |cver| # Client sets min_version ctx1 = OpenSSL::SSL::SSLContext.new ctx1.min_version = cver server_connect(port, ctx1) { |ssl| assert_equal vmap[supported.last][:name], ssl.ssl_version } # Client sets max_version ctx2 = OpenSSL::SSL::SSLContext.new ctx2.max_version = cver if cver >= sver server_connect(port, ctx2) { |ssl| assert_equal vmap[cver][:name], ssl.ssl_version } else assert_handshake_error { server_connect(port, ctx2) { } } end end } # Server sets max_version (latest is disabled) sver = supported[-2] ctx_proc = proc { |ctx| ctx.max_version = sver } start_server(ctx_proc: ctx_proc, ignore_listener_error: true) { |port| supported.each do |cver| # Client sets min_version ctx1 = OpenSSL::SSL::SSLContext.new ctx1.min_version = cver if cver <= sver server_connect(port, ctx1) { |ssl| assert_equal vmap[sver][:name], ssl.ssl_version } else assert_handshake_error { server_connect(port, ctx1) { } } end # Client sets max_version ctx2 = OpenSSL::SSL::SSLContext.new ctx2.max_version = cver server_connect(port, ctx2) { |ssl| if cver >= sver assert_equal vmap[sver][:name], ssl.ssl_version else assert_equal vmap[cver][:name], ssl.ssl_version end } end } end def test_options_disable_versions # Note: Use of these OP_* flags has been deprecated since OpenSSL 1.1.0. supported = check_supported_protocol_versions if supported.include?(OpenSSL::SSL::TLS1_1_VERSION) && supported.include?(OpenSSL::SSL::TLS1_2_VERSION) # Server disables ~ TLS 1.1 ctx_proc = proc { |ctx| ctx.options |= OpenSSL::SSL::OP_NO_SSLv2 | OpenSSL::SSL::OP_NO_SSLv3 | OpenSSL::SSL::OP_NO_TLSv1 | OpenSSL::SSL::OP_NO_TLSv1_1 } start_server(ctx_proc: ctx_proc, ignore_listener_error: true) { |port| # Client only supports TLS 1.1 ctx1 = OpenSSL::SSL::SSLContext.new ctx1.min_version = ctx1.max_version = OpenSSL::SSL::TLS1_1_VERSION assert_handshake_error { server_connect(port, ctx1) { } } # Client only supports TLS 1.2 ctx2 = OpenSSL::SSL::SSLContext.new ctx2.min_version = ctx2.max_version = OpenSSL::SSL::TLS1_2_VERSION assert_nothing_raised { server_connect(port, ctx2) { } } } # Server only supports TLS 1.1 ctx_proc = proc { |ctx| ctx.min_version = ctx.max_version = OpenSSL::SSL::TLS1_1_VERSION } start_server(ctx_proc: ctx_proc, ignore_listener_error: true) { |port| # Client disables TLS 1.1 ctx1 = OpenSSL::SSL::SSLContext.new ctx1.options |= OpenSSL::SSL::OP_NO_TLSv1_1 assert_handshake_error { server_connect(port, ctx1) { } } # Client disables TLS 1.2 ctx2 = OpenSSL::SSL::SSLContext.new ctx2.options |= OpenSSL::SSL::OP_NO_TLSv1_2 assert_nothing_raised { server_connect(port, ctx2) { } } } else pend "TLS 1.1 and TLS 1.2 must be supported; skipping" end end def test_ssl_methods_constant EnvUtil.suppress_warning { # Deprecated in v2.1.0 base = [:TLSv1_2, :TLSv1_1, :TLSv1, :SSLv3, :SSLv2, :SSLv23] base.each do |name| assert_include OpenSSL::SSL::SSLContext::METHODS, name assert_include OpenSSL::SSL::SSLContext::METHODS, :"#{name}_client" assert_include OpenSSL::SSL::SSLContext::METHODS, :"#{name}_server" end } end def test_renegotiation_cb num_handshakes = 0 renegotiation_cb = Proc.new { |ssl| num_handshakes += 1 } ctx_proc = Proc.new { |ctx| ctx.renegotiation_cb = renegotiation_cb } start_server_version(:SSLv23, ctx_proc) { |port| server_connect(port) { |ssl| assert_equal(1, num_handshakes) } } end if openssl?(1, 0, 2) || libressl? def test_alpn_protocol_selection_ary advertised = ["http/1.1", "spdy/2"] ctx_proc = Proc.new { |ctx| ctx.alpn_select_cb = -> (protocols) { protocols.first } ctx.alpn_protocols = advertised } start_server_version(:SSLv23, ctx_proc) { |port| ctx = OpenSSL::SSL::SSLContext.new ctx.alpn_protocols = advertised server_connect(port, ctx) { |ssl| assert_equal(advertised.first, ssl.alpn_protocol) } } end def test_alpn_protocol_selection_cancel sock1, sock2 = socketpair ctx1 = OpenSSL::SSL::SSLContext.new ctx1.cert = @svr_cert ctx1.key = @svr_key ctx1.tmp_dh_callback = proc { Fixtures.pkey_dh("dh1024") } ctx1.alpn_select_cb = -> (protocols) { nil } ssl1 = OpenSSL::SSL::SSLSocket.new(sock1, ctx1) ctx2 = OpenSSL::SSL::SSLContext.new ctx2.alpn_protocols = ["http/1.1"] ssl2 = OpenSSL::SSL::SSLSocket.new(sock2, ctx2) t = Thread.new { ssl2.connect_nonblock(exception: false) } assert_raise_with_message(TypeError, /nil/) { ssl1.accept } t.join ensure sock1&.close sock2&.close ssl1&.close ssl2&.close t&.kill t&.join end end def test_npn_protocol_selection_ary pend "TLS 1.2 is not supported" unless tls12_supported? pend "NPN is not supported" unless \ OpenSSL::SSL::SSLContext.method_defined?(:npn_select_cb) pend "LibreSSL 2.6 has broken NPN functions" if libressl?(2, 6, 1) advertised = ["http/1.1", "spdy/2"] ctx_proc = proc { |ctx| ctx.npn_protocols = advertised } start_server_version(:TLSv1_2, ctx_proc) { |port| selector = lambda { |which| ctx = OpenSSL::SSL::SSLContext.new ctx.npn_select_cb = -> (protocols) { protocols.send(which) } server_connect(port, ctx) { |ssl| assert_equal(advertised.send(which), ssl.npn_protocol) } } selector.call(:first) selector.call(:last) } end def test_npn_protocol_selection_enum pend "TLS 1.2 is not supported" unless tls12_supported? pend "NPN is not supported" unless \ OpenSSL::SSL::SSLContext.method_defined?(:npn_select_cb) pend "LibreSSL 2.6 has broken NPN functions" if libressl?(2, 6, 1) advertised = Object.new def advertised.each yield "http/1.1" yield "spdy/2" end ctx_proc = Proc.new { |ctx| ctx.npn_protocols = advertised } start_server_version(:TLSv1_2, ctx_proc) { |port| selector = lambda { |selected, which| ctx = OpenSSL::SSL::SSLContext.new ctx.npn_select_cb = -> (protocols) { protocols.to_a.send(which) } server_connect(port, ctx) { |ssl| assert_equal(selected, ssl.npn_protocol) } } selector.call("http/1.1", :first) selector.call("spdy/2", :last) } end def test_npn_protocol_selection_cancel pend "TLS 1.2 is not supported" unless tls12_supported? pend "NPN is not supported" unless \ OpenSSL::SSL::SSLContext.method_defined?(:npn_select_cb) pend "LibreSSL 2.6 has broken NPN functions" if libressl?(2, 6, 1) ctx_proc = Proc.new { |ctx| ctx.npn_protocols = ["http/1.1"] } start_server_version(:TLSv1_2, ctx_proc) { |port| ctx = OpenSSL::SSL::SSLContext.new ctx.npn_select_cb = -> (protocols) { raise RuntimeError.new } assert_raise(RuntimeError) { server_connect(port, ctx) } } end def test_npn_advertised_protocol_too_long pend "TLS 1.2 is not supported" unless tls12_supported? pend "NPN is not supported" unless \ OpenSSL::SSL::SSLContext.method_defined?(:npn_select_cb) pend "LibreSSL 2.6 has broken NPN functions" if libressl?(2, 6, 1) ctx_proc = Proc.new { |ctx| ctx.npn_protocols = ["a" * 256] } start_server_version(:TLSv1_2, ctx_proc) { |port| ctx = OpenSSL::SSL::SSLContext.new ctx.npn_select_cb = -> (protocols) { protocols.first } assert_handshake_error { server_connect(port, ctx) } } end def test_npn_selected_protocol_too_long pend "TLS 1.2 is not supported" unless tls12_supported? pend "NPN is not supported" unless \ OpenSSL::SSL::SSLContext.method_defined?(:npn_select_cb) pend "LibreSSL 2.6 has broken NPN functions" if libressl?(2, 6, 1) ctx_proc = Proc.new { |ctx| ctx.npn_protocols = ["http/1.1"] } start_server_version(:TLSv1_2, ctx_proc) { |port| ctx = OpenSSL::SSL::SSLContext.new ctx.npn_select_cb = -> (protocols) { "a" * 256 } assert_handshake_error { server_connect(port, ctx) } } end def test_close_after_socket_close server_proc = proc { |ctx, ssl| # Do nothing } start_server(server_proc: server_proc) { |port| sock = TCPSocket.new("127.0.0.1", port) ssl = OpenSSL::SSL::SSLSocket.new(sock) ssl.sync_close = true ssl.connect sock.close assert_nothing_raised do ssl.close end } end def test_sync_close_without_connect Socket.open(:INET, :STREAM) {|s| ssl = OpenSSL::SSL::SSLSocket.new(s) ssl.sync_close = true ssl.close assert(s.closed?) } end def test_get_ephemeral_key # OpenSSL >= 1.0.2 unless OpenSSL::SSL::SSLSocket.method_defined?(:tmp_key) pend "SSL_get_server_tmp_key() is not supported" end if tls12_supported? # kRSA ctx_proc1 = proc { |ctx| ctx.ssl_version = :TLSv1_2 ctx.ciphers = "kRSA" } start_server(ctx_proc: ctx_proc1) do |port| ctx = OpenSSL::SSL::SSLContext.new ctx.ssl_version = :TLSv1_2 ctx.ciphers = "kRSA" server_connect(port, ctx) { |ssl| assert_nil ssl.tmp_key } end end if defined?(OpenSSL::PKey::DH) && tls12_supported? # DHE # TODO: How to test this with TLS 1.3? ctx_proc2 = proc { |ctx| ctx.ssl_version = :TLSv1_2 ctx.ciphers = "EDH" } start_server(ctx_proc: ctx_proc2) do |port| ctx = OpenSSL::SSL::SSLContext.new ctx.ssl_version = :TLSv1_2 ctx.ciphers = "EDH" server_connect(port, ctx) { |ssl| assert_instance_of OpenSSL::PKey::DH, ssl.tmp_key } end end if defined?(OpenSSL::PKey::EC) # ECDHE ctx_proc3 = proc { |ctx| ctx.ciphers = "DEFAULT:!kRSA:!kEDH" ctx.ecdh_curves = "P-256" } start_server(ctx_proc: ctx_proc3) do |port| ctx = OpenSSL::SSL::SSLContext.new ctx.ciphers = "DEFAULT:!kRSA:!kEDH" server_connect(port, ctx) { |ssl| assert_instance_of OpenSSL::PKey::EC, ssl.tmp_key } end end end def test_dh_callback pend "TLS 1.2 is not supported" unless tls12_supported? called = false ctx_proc = -> ctx { ctx.ssl_version = :TLSv1_2 ctx.ciphers = "DH:!NULL" ctx.tmp_dh_callback = ->(*args) { called = true Fixtures.pkey_dh("dh1024") } } start_server(ctx_proc: ctx_proc) do |port| server_connect(port) { |ssl| assert called, "dh callback should be called" if ssl.respond_to?(:tmp_key) assert_equal Fixtures.pkey_dh("dh1024").to_der, ssl.tmp_key.to_der end } end end def test_connect_works_when_setting_dh_callback_to_nil pend "TLS 1.2 is not supported" unless tls12_supported? ctx_proc = -> ctx { ctx.ssl_version = :TLSv1_2 ctx.ciphers = "DH:!NULL" # use DH ctx.tmp_dh_callback = nil } start_server(ctx_proc: ctx_proc) do |port| EnvUtil.suppress_warning { # uses default callback assert_nothing_raised { server_connect(port) { } } } end end def test_tmp_ecdh_callback pend "EC is disabled" unless defined?(OpenSSL::PKey::EC) pend "tmp_ecdh_callback is not supported" unless \ OpenSSL::SSL::SSLContext.method_defined?(:tmp_ecdh_callback) pend "LibreSSL 2.6 has broken SSL_CTX_set_tmp_ecdh_callback()" \ if libressl?(2, 6, 1) EnvUtil.suppress_warning do # tmp_ecdh_callback is deprecated (2016-05) called = false ctx_proc = -> ctx { ctx.ciphers = "DEFAULT:!kRSA:!kEDH" ctx.tmp_ecdh_callback = -> (*args) { called = true OpenSSL::PKey::EC.new "prime256v1" } } start_server(ctx_proc: ctx_proc) do |port| server_connect(port) { |s| assert called, "tmp_ecdh_callback should be called" } end end end def test_ecdh_curves pend "EC is disabled" unless defined?(OpenSSL::PKey::EC) ctx_proc = -> ctx { # Enable both ECDHE (~ TLS 1.2) cipher suites and TLS 1.3 ctx.ciphers = "DEFAULT:!kRSA:!kEDH" ctx.ecdh_curves = "P-384:P-521" } start_server(ctx_proc: ctx_proc, ignore_listener_error: true) do |port| ctx = OpenSSL::SSL::SSLContext.new ctx.ecdh_curves = "P-256:P-384" # disable P-521 for OpenSSL >= 1.0.2 server_connect(port, ctx) { |ssl| cs = ssl.cipher[0] if /\ATLS/ =~ cs # Is TLS 1.3 is used? assert_equal "secp384r1", ssl.tmp_key.group.curve_name else assert_match (/\AECDH/), cs if ssl.respond_to?(:tmp_key) assert_equal "secp384r1", ssl.tmp_key.group.curve_name end end } if openssl?(1, 0, 2) || libressl?(2, 5, 1) ctx = OpenSSL::SSL::SSLContext.new ctx.ecdh_curves = "P-256" assert_raise(OpenSSL::SSL::SSLError) { server_connect(port, ctx) { } } ctx = OpenSSL::SSL::SSLContext.new ctx.ecdh_curves = "P-521:P-384" server_connect(port, ctx) { |ssl| assert_equal "secp521r1", ssl.tmp_key.group.curve_name } end end end def test_security_level ctx = OpenSSL::SSL::SSLContext.new begin ctx.security_level = 1 rescue NotImplementedError assert_equal(0, ctx.security_level) return end assert_equal(1, ctx.security_level) # assert_raise(OpenSSL::SSL::SSLError) { ctx.key = Fixtures.pkey("dsa512") } # ctx.key = Fixtures.pkey("rsa1024") # ctx.security_level = 2 # assert_raise(OpenSSL::SSL::SSLError) { ctx.key = Fixtures.pkey("rsa1024") } pend "FIXME: SSLContext#key= currently does not raise because SSL_CTX_use_certificate() is delayed" end def test_dup ctx = OpenSSL::SSL::SSLContext.new sock1, sock2 = socketpair ssl = OpenSSL::SSL::SSLSocket.new(sock1, ctx) assert_raise(NoMethodError) { ctx.dup } assert_raise(NoMethodError) { ssl.dup } ensure ssl.close if ssl sock1.close sock2.close end def test_freeze_calls_setup bug = "[ruby/openssl#85]" start_server(ignore_listener_error: true) { |port| ctx = OpenSSL::SSL::SSLContext.new ctx.verify_mode = OpenSSL::SSL::VERIFY_PEER ctx.freeze assert_raise(OpenSSL::SSL::SSLError, bug) { server_connect(port, ctx) } } end private def start_server_version(version, ctx_proc = nil, server_proc = method(:readwrite_loop), &blk) ctx_wrap = Proc.new { |ctx| ctx.ssl_version = version ctx_proc.call(ctx) if ctx_proc } start_server( ctx_proc: ctx_wrap, server_proc: server_proc, ignore_listener_error: true, &blk ) end def server_connect(port, ctx = nil) sock = TCPSocket.new("127.0.0.1", port) ssl = ctx ? OpenSSL::SSL::SSLSocket.new(sock, ctx) : OpenSSL::SSL::SSLSocket.new(sock) ssl.sync_close = true ssl.connect yield ssl if block_given? ensure if ssl ssl.close elsif sock sock.close end end def assert_handshake_error # different OpenSSL versions react differently when facing a SSL/TLS version # that has been marked as forbidden, therefore either of these may be raised assert_raise(OpenSSL::SSL::SSLError, Errno::ECONNRESET) { yield } end end end