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ruby--ruby/test/openssl/test_ssl.rb
Christophe De La Fuente 17998ad3bb [ruby/openssl] Add support to SSL_CTX_set_keylog_callback
- This callback is invoked when TLS key material is generated or
  received, in order to allow applications to store this keying material
  for debugging purposes.
- It is invoked with an `SSLSocket` and a string containing the key
  material in the format used by NSS for its SSLKEYLOGFILE debugging
  output.
- This commit adds the Ruby binding `keylog_cb` and the related tests
- It is only compatible with OpenSSL >= 1.1.1. Even if LibreSSL implements
  `SSL_CTX_set_keylog_callback()` from v3.4.2, it does nothing (see
  648d39f0f0)

https://github.com/ruby/openssl/commit/3b63232cf1
2022-10-17 16:35:35 +09:00

1920 lines
64 KiB
Ruby

# frozen_string_literal: true
require_relative "utils"
if defined?(OpenSSL)
class OpenSSL::TestSSL < OpenSSL::SSLTestCase
def test_bad_socket
bad_socket = Struct.new(:sync).new
assert_raise TypeError do
socket = OpenSSL::SSL::SSLSocket.new bad_socket
# if the socket is not a T_FILE, `connect` will segv because it tries
# to get the underlying file descriptor but the API it calls assumes
# the object type is T_FILE
socket.connect
end
end
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
ssl.puts "abc"; assert_equal "abc\n", ssl.gets
ensure
ssl&.close
sock&.close
end
}
end
def test_socket_open
start_server { |port|
begin
ssl = OpenSSL::SSL::SSLSocket.open("127.0.0.1", port)
ssl.sync_close = true
ssl.connect
ssl.puts "abc"; assert_equal "abc\n", ssl.gets
ensure
ssl&.close
end
}
end
def test_socket_open_with_context
start_server { |port|
begin
ctx = OpenSSL::SSL::SSLContext.new
ssl = OpenSSL::SSL::SSLSocket.open("127.0.0.1", port, context: ctx)
ssl.sync_close = true
ssl.connect
assert_equal ssl.context, ctx
ssl.puts "abc"; assert_equal "abc\n", ssl.gets
ensure
ssl&.close
end
}
end
def test_socket_open_with_local_address_port_context
start_server { |port|
begin
# Guess a free port number
random_port = rand(49152..65535)
ctx = OpenSSL::SSL::SSLContext.new
ssl = OpenSSL::SSL::SSLSocket.open("127.0.0.1", port, "127.0.0.1", random_port, context: ctx)
ssl.sync_close = true
ssl.connect
assert_equal ctx, ssl.context
assert_equal random_port, ssl.io.local_address.ip_port
ssl.puts "abc"; assert_equal "abc\n", ssl.gets
rescue Errno::EADDRINUSE, Errno::EACCES
ensure
ssl&.close
end
}
end
def test_add_certificate
ctx_proc = -> ctx {
# Unset values set by start_server
ctx.cert = ctx.key = ctx.extra_chain_cert = nil
ctx.add_certificate(@svr_cert, @svr_key, [@ca_cert]) # RSA
}
start_server(ctx_proc: ctx_proc) do |port|
server_connect(port) { |ssl|
assert_equal @svr_cert.subject, ssl.peer_cert.subject
assert_equal [@svr_cert.subject, @ca_cert.subject],
ssl.peer_cert_chain.map(&:subject)
ssl.puts "abc"; assert_equal "abc\n", ssl.gets
}
end
end
def test_add_certificate_multiple_certs
ca2_key = Fixtures.pkey("rsa-3")
ca2_exts = [
["basicConstraints", "CA:TRUE", true],
["keyUsage", "cRLSign, keyCertSign", true],
]
ca2_dn = OpenSSL::X509::Name.parse_rfc2253("CN=CA2")
ca2_cert = issue_cert(ca2_dn, ca2_key, 123, ca2_exts, nil, nil)
ecdsa_key = Fixtures.pkey("p256")
exts = [
["keyUsage", "digitalSignature", false],
]
ecdsa_dn = OpenSSL::X509::Name.parse_rfc2253("CN=localhost2")
ecdsa_cert = issue_cert(ecdsa_dn, ecdsa_key, 456, exts, ca2_cert, ca2_key)
ctx_proc = -> ctx {
# Unset values set by start_server
ctx.cert = ctx.key = ctx.extra_chain_cert = nil
ctx.add_certificate(@svr_cert, @svr_key, [@ca_cert]) # RSA
ctx.add_certificate(ecdsa_cert, ecdsa_key, [ca2_cert])
}
start_server(ctx_proc: ctx_proc) do |port|
ctx = OpenSSL::SSL::SSLContext.new
ctx.max_version = :TLS1_2 # TODO: We need this to force certificate type
ctx.ciphers = "aECDSA"
server_connect(port, ctx) { |ssl|
assert_equal ecdsa_cert.subject, ssl.peer_cert.subject
assert_equal [ecdsa_cert.subject, ca2_cert.subject],
ssl.peer_cert_chain.map(&:subject)
}
ctx = OpenSSL::SSL::SSLContext.new
ctx.max_version = :TLS1_2
ctx.ciphers = "aRSA"
server_connect(port, ctx) { |ssl|
assert_equal @svr_cert.subject, ssl.peer_cert.subject
assert_equal [@svr_cert.subject, @ca_cert.subject],
ssl.peer_cert_chain.map(&:subject)
}
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 = String.new
ssl.syswrite(str)
assert_same buf, ssl.sysread(str.size, buf)
assert_equal(str, buf)
}
}
end
def test_getbyte
start_server { |port|
server_connect(port) { |ssl|
str = +("x" * 100 + "\n")
ssl.syswrite(str)
newstr = str.bytesize.times.map { |i|
ssl.getbyte
}.pack("C*")
assert_equal(str, newstr)
}
}
end
def test_sync_close
start_server do |port|
begin
sock = TCPSocket.new("127.0.0.1", port)
ssl = OpenSSL::SSL::SSLSocket.new(sock)
ssl.connect
ssl.puts "abc"; assert_equal "abc\n", ssl.gets
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.puts "abc"; assert_equal "abc\n", ssl.gets
ssl.close
assert_predicate sock, :closed?
ensure
sock&.close
end
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_verify_mode_default
ctx = OpenSSL::SSL::SSLContext.new
assert_equal OpenSSL::SSL::VERIFY_NONE, ctx.verify_mode
end
def test_verify_mode_server_cert
start_server(ignore_listener_error: true) { |port|
populated_store = OpenSSL::X509::Store.new
populated_store.add_cert(@ca_cert)
empty_store = OpenSSL::X509::Store.new
# Valid certificate, SSL_VERIFY_PEER
assert_nothing_raised {
ctx = OpenSSL::SSL::SSLContext.new
ctx.verify_mode = OpenSSL::SSL::VERIFY_PEER
ctx.cert_store = populated_store
server_connect(port, ctx) { |ssl| ssl.puts("abc"); ssl.gets }
}
# Invalid certificate, SSL_VERIFY_NONE
assert_nothing_raised {
ctx = OpenSSL::SSL::SSLContext.new
ctx.verify_mode = OpenSSL::SSL::VERIFY_NONE
ctx.cert_store = empty_store
server_connect(port, ctx) { |ssl| ssl.puts("abc"); ssl.gets }
}
# Invalid certificate, SSL_VERIFY_PEER
assert_handshake_error {
ctx = OpenSSL::SSL::SSLContext.new
ctx.verify_mode = OpenSSL::SSL::VERIFY_PEER
ctx.cert_store = empty_store
server_connect(port, ctx) { |ssl| ssl.puts("abc"); ssl.gets }
}
}
end
def test_verify_mode_client_cert_required
# Optional, client certificate not supplied
vflag = OpenSSL::SSL::VERIFY_PEER
accept_proc = -> ssl {
assert_equal nil, ssl.peer_cert
}
start_server(verify_mode: vflag, accept_proc: accept_proc) { |port|
assert_nothing_raised {
server_connect(port) { |ssl| ssl.puts("abc"); ssl.gets }
}
}
# Required, client certificate not supplied
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,
ctx_proc: proc { |ctx|
ctx.max_version = OpenSSL::SSL::TLS1_2_VERSION if libressl?(3, 2, 0)
}) { |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_cert_cb_ignore_error
vflag = OpenSSL::SSL::VERIFY_PEER|OpenSSL::SSL::VERIFY_FAIL_IF_NO_PEER_CERT
start_server(verify_mode: vflag, ignore_listener_error: true) do |port|
ctx = OpenSSL::SSL::SSLContext.new
ctx.client_cert_cb = -> ssl {
raise "exception in client_cert_cb must be suppressed"
}
# 1. Exception in client_cert_cb is suppressed
# 2. No client certificate will be sent to the server
# 3. SSL_VERIFY_FAIL_IF_NO_PEER_CERT causes the handshake to fail
assert_handshake_error {
server_connect(port, ctx) { |ssl| ssl.puts("abc"); ssl.gets }
}
end
end
def test_client_ca
pend "LibreSSL 3.2 has broken client CA support" if libressl?(3, 2, 0)
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)
ssl.puts "abc"; assert_equal "abc\n", ssl.gets
}
}
end
def test_unstarted_session
start_server do |port|
sock = TCPSocket.new("127.0.0.1", port)
ssl = OpenSSL::SSL::SSLSocket.new(sock)
assert_raise(OpenSSL::SSL::SSLError) { ssl.syswrite("data") }
assert_raise(OpenSSL::SSL::SSLError) { ssl.sysread(1) }
ssl.connect
ssl.puts "abc"
assert_equal "abc\n", ssl.gets
ensure
ssl&.close
sock&.close
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|
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
server_connect(port, ctx) { |ssl|
assert_equal(OpenSSL::X509::V_OK, ssl.verify_result)
ssl.puts "abc"; assert_equal "abc\n", ssl.gets
}
}
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_finished_messages
server_finished = nil
server_peer_finished = nil
client_finished = nil
client_peer_finished = nil
start_server(accept_proc: proc { |server|
server_finished = server.finished_message
server_peer_finished = server.peer_finished_message
}, ctx_proc: proc { |ctx|
ctx.max_version = OpenSSL::SSL::TLS1_2_VERSION if libressl?(3, 2, 0)
}) { |port|
ctx = OpenSSL::SSL::SSLContext.new
ctx.verify_mode = OpenSSL::SSL::VERIFY_NONE
ctx.max_version = :TLS1_2 if libressl?(3, 2, 0) && !libressl?(3, 3, 0)
server_connect(port, ctx) { |ssl|
ssl.puts "abc"; ssl.gets
client_finished = ssl.finished_message
client_peer_finished = ssl.peer_finished_message
}
}
assert_not_nil(server_finished)
assert_not_nil(client_finished)
assert_equal(server_finished, client_peer_finished)
assert_equal(server_peer_finished, client_finished)
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
ctx_proc = -> ctx {
ctx.ssl_version = :TLSv1_2
ctx.ciphers = "aNULL"
ctx.tmp_dh = Fixtures.pkey("dh-1")
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|
ssl.puts "abc"; assert_equal "abc\n", ssl.gets
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,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|
ssl.puts "abc"; assert_equal "abc\n", ssl.gets
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|
ssl.puts "abc"; assert_equal "abc\n", ssl.gets
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(true, OpenSSL::SSL.verify_certificate_identity(cert, '13::17'))
assert_equal(false, OpenSSL::SSL.verify_certificate_identity(cert, '13::18'))
assert_equal(true, OpenSSL::SSL.verify_certificate_identity(cert, '13:0:0:0:0:0:0:17'))
assert_equal(false, OpenSSL::SSL.verify_certificate_identity(cert, '44:0:0:0:0:0:0:17'))
assert_equal(true, OpenSSL::SSL.verify_certificate_identity(cert, '0013:0000:0000:0000:0000:0000:0000:0017'))
assert_equal(false, OpenSSL::SSL.verify_certificate_identity(cert, '1313:0000:0000:0000:0000:0000:0000:0017'))
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'))
# LibreSSL 3.5.0+ doesn't support other wildcard certificates
# (it isn't required to, as RFC states MAY, not MUST)
return if libressl?(3, 5, 0)
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_keylog_cb
pend "Keylog callback is not supported" if !openssl?(1, 1, 1) || libressl?
prefix = 'CLIENT_RANDOM'
context = OpenSSL::SSL::SSLContext.new
context.min_version = context.max_version = OpenSSL::SSL::TLS1_2_VERSION
cb_called = false
context.keylog_cb = proc do |_sock, line|
cb_called = true
assert_equal(prefix, line.split.first)
end
start_server do |port|
server_connect(port, context) do |ssl|
ssl.puts "abc"
assert_equal("abc\n", ssl.gets)
assert_equal(true, cb_called)
end
end
if tls13_supported?
prefixes = [
'SERVER_HANDSHAKE_TRAFFIC_SECRET',
'EXPORTER_SECRET',
'SERVER_TRAFFIC_SECRET_0',
'CLIENT_HANDSHAKE_TRAFFIC_SECRET',
'CLIENT_TRAFFIC_SECRET_0',
]
context = OpenSSL::SSL::SSLContext.new
context.min_version = context.max_version = OpenSSL::SSL::TLS1_3_VERSION
cb_called = false
context.keylog_cb = proc do |_sock, line|
cb_called = true
assert_not_nil(prefixes.delete(line.split.first))
end
start_server do |port|
server_connect(port, context) do |ssl|
ssl.puts "abc"
assert_equal("abc\n", ssl.gets)
assert_equal(true, cb_called)
end
assert_equal(0, prefixes.size)
end
end
end
def test_tlsext_hostname
fooctx = OpenSSL::SSL::SSLContext.new
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?
ssl.puts "abc"; assert_equal "abc\n", ssl.gets
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
ssl.puts "abc"; assert_equal "abc\n", ssl.gets
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.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_accept_errors_include_peeraddr
context = OpenSSL::SSL::SSLContext.new
context.cert = @svr_cert
context.key = @svr_key
server = TCPServer.new("127.0.0.1", 0)
port = server.connect_address.ip_port
ssl_server = OpenSSL::SSL::SSLServer.new(server, context)
t = Thread.new do
assert_raise_with_message(OpenSSL::SSL::SSLError, /peeraddr=127\.0\.0\.1/) do
ssl_server.accept
end
end
sock = TCPSocket.new("127.0.0.1", port)
sock << "\x00" * 1024
assert t.join
ensure
sock&.close
server.close
end
def test_verify_hostname_on_connect
ctx_proc = proc { |ctx|
san = "DNS:a.example.com,DNS:*.b.example.com"
san += ",DNS:c*.example.com,DNS:d.*.example.com" unless libressl?(3, 2, 2)
exts = [
["keyUsage", "keyEncipherment,digitalSignature", true],
["subjectAltName", san],
]
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
assert_equal false, ctx.verify_hostname
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|
next if name.start_with?('cx') if libressl?(3, 2, 2)
begin
sock = TCPSocket.new("127.0.0.1", port)
ssl = OpenSSL::SSL::SSLSocket.new(sock, ctx)
ssl.hostname = name
if expected_ok
ssl.connect
ssl.puts "abc"; assert_equal "abc\n", ssl.gets
else
assert_handshake_error { ssl.connect }
end
ensure
ssl.close if ssl
sock.close if sock
end
end
end
end
def test_verify_hostname_failure_error_code
ctx_proc = proc { |ctx|
exts = [
["keyUsage", "keyEncipherment,digitalSignature", true],
["subjectAltName", "DNS:a.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|
verify_callback_ok = verify_callback_err = nil
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
ctx.verify_callback = -> (preverify_ok, store_ctx) {
verify_callback_ok = preverify_ok
verify_callback_err = store_ctx.error
preverify_ok
}
begin
sock = TCPSocket.new("127.0.0.1", port)
ssl = OpenSSL::SSL::SSLSocket.new(sock, ctx)
ssl.hostname = "b.example.com"
assert_handshake_error { ssl.connect }
assert_equal false, verify_callback_ok
assert_equal OpenSSL::X509::V_ERR_HOSTNAME_MISMATCH, verify_callback_err
ensure
sock&.close
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
# OpenSSL <= 1.1.0: "self signed certificate in certificate chain"
# OpenSSL >= 3.0.0: "self-signed certificate in certificate chain"
assert_raise_with_message(OpenSSL::SSL::SSLError, /self.signed/) {
server_connect(port, ctx)
}
}
ctx_proc = proc { |ctx|
now = Time.now
ctx.cert = issue_cert(@svr, @svr_key, 30, [], @ca_cert, @ca_key,
not_before: now - 7200, not_after: now - 3600)
}
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) { |ssl|
ssl.puts "abc"; assert_equal "abc\n", ssl.gets
}
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
ssl.puts "abc"; assert_equal "abc\n", ssl.gets
}
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
ssl.puts "abc"; assert_equal "abc\n", ssl.gets
}
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
ssl.puts "abc"; assert_equal "abc\n", ssl.gets
}
}
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
ssl.puts "abc"; assert_equal "abc\n", ssl.gets
}
# 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
ssl.puts "abc"; assert_equal "abc\n", ssl.gets
}
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
ssl.puts "abc"; assert_equal "abc\n", ssl.gets
}
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
ssl.puts "abc"; assert_equal "abc\n", ssl.gets
}
end
}
end
def test_options_disable_versions
# It's recommended to use SSLContext#{min,max}_version= instead in real
# applications. The purpose of this test case is to check that SSL options
# are properly propagated to OpenSSL library.
supported = check_supported_protocol_versions
if !defined?(OpenSSL::SSL::TLS1_3_VERSION) ||
!supported.include?(OpenSSL::SSL::TLS1_2_VERSION) ||
!supported.include?(OpenSSL::SSL::TLS1_3_VERSION) ||
!defined?(OpenSSL::SSL::OP_NO_TLSv1_3) # LibreSSL < 3.4
pend "this test case requires both TLS 1.2 and TLS 1.3 to be supported " \
"and enabled by default"
end
# Server disables TLS 1.2 and earlier
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 |
OpenSSL::SSL::OP_NO_TLSv1_2
}
start_server(ctx_proc: ctx_proc, ignore_listener_error: true) { |port|
# Client only supports TLS 1.2
ctx1 = OpenSSL::SSL::SSLContext.new
ctx1.min_version = ctx1.max_version = OpenSSL::SSL::TLS1_2_VERSION
assert_handshake_error { server_connect(port, ctx1) { } }
# Client only supports TLS 1.3
ctx2 = OpenSSL::SSL::SSLContext.new
ctx2.min_version = ctx2.max_version = OpenSSL::SSL::TLS1_3_VERSION
assert_nothing_raised { server_connect(port, ctx2) { } }
}
# Server only supports TLS 1.2
ctx_proc = proc { |ctx|
ctx.min_version = ctx.max_version = OpenSSL::SSL::TLS1_2_VERSION
}
start_server(ctx_proc: ctx_proc, ignore_listener_error: true) { |port|
# Client doesn't support TLS 1.2
ctx1 = OpenSSL::SSL::SSLContext.new
ctx1.options |= OpenSSL::SSL::OP_NO_TLSv1_2
assert_handshake_error { server_connect(port, ctx1) { } }
# Client supports TLS 1.2 by default
ctx2 = OpenSSL::SSL::SSLContext.new
ctx2.options |= OpenSSL::SSL::OP_NO_TLSv1_3
assert_nothing_raised { server_connect(port, ctx2) { } }
}
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)
ssl.puts "abc"; assert_equal "abc\n", ssl.gets
}
}
end
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)
ssl.puts "abc"; assert_equal "abc\n", ssl.gets
}
}
end
def test_alpn_protocol_selection_cancel
sock1, sock2 = socketpair
ctx1 = OpenSSL::SSL::SSLContext.new
ctx1.cert = @svr_cert
ctx1.key = @svr_key
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
def test_npn_protocol_selection_ary
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 "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 "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 "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 "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 readwrite_loop_safe(ctx, ssl)
readwrite_loop(ctx, ssl)
rescue OpenSSL::SSL::SSLError
end
def test_close_after_socket_close
start_server(server_proc: method(:readwrite_loop_safe)) { |port|
sock = TCPSocket.new("127.0.0.1", port)
ssl = OpenSSL::SSL::SSLSocket.new(sock)
ssl.connect
ssl.puts "abc"; assert_equal "abc\n", ssl.gets
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
# kRSA
ctx_proc1 = proc { |ctx|
ctx.ssl_version = :TLSv1_2
ctx.ciphers = "kRSA"
}
start_server(ctx_proc: ctx_proc1, ignore_listener_error: true) do |port|
ctx = OpenSSL::SSL::SSLContext.new
ctx.ssl_version = :TLSv1_2
ctx.ciphers = "kRSA"
begin
server_connect(port, ctx) { |ssl| assert_nil ssl.tmp_key }
rescue OpenSSL::SSL::SSLError
# kRSA seems disabled
raise unless $!.message =~ /no cipher/
end
end
# DHE
# TODO: How to test this with TLS 1.3?
ctx_proc2 = proc { |ctx|
ctx.ssl_version = :TLSv1_2
ctx.ciphers = "EDH"
ctx.tmp_dh = Fixtures.pkey("dh-1")
}
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
# 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
ssl.puts "abc"; assert_equal "abc\n", ssl.gets
}
end
end
def test_fallback_scsv
supported = check_supported_protocol_versions
return unless supported.include?(OpenSSL::SSL::TLS1_1_VERSION) &&
supported.include?(OpenSSL::SSL::TLS1_2_VERSION)
pend "Fallback SCSV is not supported" unless \
OpenSSL::SSL::SSLContext.method_defined?(:enable_fallback_scsv)
start_server do |port|
ctx = OpenSSL::SSL::SSLContext.new
ctx.max_version = OpenSSL::SSL::TLS1_2_VERSION
# Here is OK
# TLS1.2 supported and this is what we ask the first time
server_connect(port, ctx)
end
ctx_proc = proc { |ctx|
ctx.max_version = OpenSSL::SSL::TLS1_1_VERSION
}
start_server(ctx_proc: ctx_proc) do |port|
ctx = OpenSSL::SSL::SSLContext.new
ctx.enable_fallback_scsv
ctx.max_version = OpenSSL::SSL::TLS1_1_VERSION
# Here is OK too
# TLS1.2 not supported, fallback to TLS1.1 and signaling the fallback
# Server doesn't support better, so connection OK
server_connect(port, ctx)
end
# Here is not OK
# TLS1.2 is supported, fallback to TLS1.1 (downgrade attack) and signaling the fallback
# Server support better, so refuse the connection
sock1, sock2 = socketpair
begin
# This test is for the downgrade protection mechanism of TLS1.2.
# This is why ctx1 bounds max_version == TLS1.2.
# Otherwise, this test fails when using openssl 1.1.1 (or later) that supports TLS1.3.
# TODO: We may need another test for TLS1.3 because it seems to have a different mechanism.
ctx1 = OpenSSL::SSL::SSLContext.new
ctx1.max_version = OpenSSL::SSL::TLS1_2_VERSION
s1 = OpenSSL::SSL::SSLSocket.new(sock1, ctx1)
ctx2 = OpenSSL::SSL::SSLContext.new
ctx2.enable_fallback_scsv
ctx2.max_version = OpenSSL::SSL::TLS1_1_VERSION
s2 = OpenSSL::SSL::SSLSocket.new(sock2, ctx2)
t = Thread.new {
assert_raise_with_message(OpenSSL::SSL::SSLError, /inappropriate fallback/) {
s2.connect
}
}
assert_raise_with_message(OpenSSL::SSL::SSLError, /inappropriate fallback/) {
s1.accept
}
t.join
ensure
sock1.close
sock2.close
end
end
def test_tmp_dh_callback
dh = Fixtures.pkey("dh-1")
called = false
ctx_proc = -> ctx {
ctx.max_version = :TLS1_2
ctx.ciphers = "DH:!NULL"
ctx.tmp_dh_callback = ->(*args) {
called = true
dh
}
}
start_server(ctx_proc: ctx_proc) do |port|
server_connect(port) { |ssl|
assert called, "dh callback should be called"
assert_equal dh.to_der, ssl.tmp_key.to_der
}
end
end
def test_ciphersuites_method_tls_connection
ssl_ctx = OpenSSL::SSL::SSLContext.new
if !tls13_supported? || !ssl_ctx.respond_to?(:ciphersuites=)
pend 'TLS 1.3 not supported'
end
csuite = ['TLS_AES_128_GCM_SHA256', 'TLSv1.3', 128, 128]
inputs = [csuite[0], [csuite[0]], [csuite]]
start_server do |port|
inputs.each do |input|
cli_ctx = OpenSSL::SSL::SSLContext.new
cli_ctx.min_version = cli_ctx.max_version = OpenSSL::SSL::TLS1_3_VERSION
cli_ctx.ciphersuites = input
server_connect(port, cli_ctx) do |ssl|
assert_equal('TLSv1.3', ssl.ssl_version)
if libressl?(3, 4, 0) && !libressl?(3, 5, 0)
assert_equal("AEAD-AES128-GCM-SHA256", ssl.cipher[0])
else
assert_equal(csuite[0], ssl.cipher[0])
end
ssl.puts('abc'); assert_equal("abc\n", ssl.gets)
end
end
end
end
def test_ciphersuites_method_nil_argument
ssl_ctx = OpenSSL::SSL::SSLContext.new
pend 'ciphersuites= method is missing' unless ssl_ctx.respond_to?(:ciphersuites=)
assert_nothing_raised { ssl_ctx.ciphersuites = nil }
end
def test_ciphersuites_method_frozen_object
ssl_ctx = OpenSSL::SSL::SSLContext.new
pend 'ciphersuites= method is missing' unless ssl_ctx.respond_to?(:ciphersuites=)
ssl_ctx.freeze
assert_raise(FrozenError) { ssl_ctx.ciphersuites = 'TLS_AES_256_GCM_SHA384' }
end
def test_ciphersuites_method_bogus_csuite
ssl_ctx = OpenSSL::SSL::SSLContext.new
pend 'ciphersuites= method is missing' unless ssl_ctx.respond_to?(:ciphersuites=)
assert_raise_with_message(
OpenSSL::SSL::SSLError,
/SSL_CTX_set_ciphersuites: no cipher match/i
) { ssl_ctx.ciphersuites = 'BOGUS' }
end
def test_ciphers_method_tls_connection
csuite = ['ECDHE-RSA-AES256-GCM-SHA384', 'TLSv1.2', 256, 256]
inputs = [csuite[0], [csuite[0]], [csuite]]
start_server do |port|
inputs.each do |input|
cli_ctx = OpenSSL::SSL::SSLContext.new
cli_ctx.min_version = cli_ctx.max_version = OpenSSL::SSL::TLS1_2_VERSION
cli_ctx.ciphers = input
server_connect(port, cli_ctx) do |ssl|
assert_equal('TLSv1.2', ssl.ssl_version)
assert_equal(csuite[0], ssl.cipher[0])
ssl.puts('abc'); assert_equal("abc\n", ssl.gets)
end
end
end
end
def test_ciphers_method_nil_argument
ssl_ctx = OpenSSL::SSL::SSLContext.new
assert_nothing_raised { ssl_ctx.ciphers = nil }
end
def test_ciphers_method_frozen_object
ssl_ctx = OpenSSL::SSL::SSLContext.new
ssl_ctx.freeze
assert_raise(FrozenError) { ssl_ctx.ciphers = 'ECDHE-RSA-AES128-SHA' }
end
def test_ciphers_method_bogus_csuite
omit "Old #{OpenSSL::OPENSSL_LIBRARY_VERSION}" if
year = OpenSSL::OPENSSL_LIBRARY_VERSION[/\A OpenSSL\s+[01]\..*\s\K\d+\z/x] and
year.to_i <= 2018
ssl_ctx = OpenSSL::SSL::SSLContext.new
assert_raise_with_message(
OpenSSL::SSL::SSLError,
/SSL_CTX_set_cipher_list: no cipher match/i
) { ssl_ctx.ciphers = 'BOGUS' }
end
def test_connect_works_when_setting_dh_callback_to_nil
ctx_proc = -> ctx {
ctx.max_version = :TLS1_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_dh
dh = Fixtures.pkey("dh-1")
ctx_proc = -> ctx {
ctx.max_version = :TLS1_2
ctx.ciphers = "DH:!NULL" # use DH
ctx.tmp_dh = dh
}
start_server(ctx_proc: ctx_proc) do |port|
server_connect(port) { |ssl|
assert_equal dh.to_der, ssl.tmp_key.to_der
}
end
end
def test_ecdh_curves_tls12
ctx_proc = -> ctx {
# Enable both ECDHE (~ TLS 1.2) cipher suites and TLS 1.3
ctx.max_version = OpenSSL::SSL::TLS1_2_VERSION
ctx.ciphers = "kEECDH"
ctx.ecdh_curves = "P-384:P-521"
}
start_server(ctx_proc: ctx_proc, ignore_listener_error: true) do |port|
# Test 1: Client=P-256:P-384, Server=P-384:P-521 --> P-384
ctx = OpenSSL::SSL::SSLContext.new
ctx.ecdh_curves = "P-256:P-384"
server_connect(port, ctx) { |ssl|
cs = ssl.cipher[0]
assert_match (/\AECDH/), cs
assert_equal "secp384r1", ssl.tmp_key.group.curve_name
ssl.puts "abc"; assert_equal "abc\n", ssl.gets
}
# Test 2: Client=P-256, Server=P-521:P-384 --> Fail
ctx = OpenSSL::SSL::SSLContext.new
ctx.ecdh_curves = "P-256"
assert_raise(OpenSSL::SSL::SSLError) {
server_connect(port, ctx) { }
}
# Test 3: Client=P-521:P-384, Server=P-521:P-384 --> P-521
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
ssl.puts "abc"; assert_equal "abc\n", ssl.gets
}
end
end
def test_ecdh_curves_tls13
pend "TLS 1.3 not supported" unless tls13_supported?
ctx_proc = -> ctx {
# Assume TLS 1.3 is enabled and chosen by default
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
server_connect(port, ctx) { |ssl|
assert_equal "TLSv1.3", ssl.ssl_version
assert_equal "secp384r1", ssl.tmp_key.group.curve_name
ssl.puts "abc"; assert_equal "abc\n", ssl.gets
}
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)
dsa512 = Fixtures.pkey("dsa512")
dsa512_cert = issue_cert(@svr, dsa512, 50, [], @ca_cert, @ca_key)
rsa1024 = Fixtures.pkey("rsa1024")
rsa1024_cert = issue_cert(@svr, rsa1024, 51, [], @ca_cert, @ca_key)
assert_raise(OpenSSL::SSL::SSLError) {
# 512 bit DSA key is rejected because it offers < 80 bits of security
ctx.add_certificate(dsa512_cert, dsa512)
}
assert_nothing_raised {
ctx.add_certificate(rsa1024_cert, rsa1024)
}
ctx.security_level = 2
assert_raise(OpenSSL::SSL::SSLError) {
# < 112 bits of security
ctx.add_certificate(rsa1024_cert, rsa1024)
}
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
def test_fileno
ctx = OpenSSL::SSL::SSLContext.new
sock1, sock2 = socketpair
socket = OpenSSL::SSL::SSLSocket.new(sock1)
server = OpenSSL::SSL::SSLServer.new(sock2, ctx)
assert_equal socket.fileno, socket.to_io.fileno
assert_equal server.fileno, server.to_io.fileno
ensure
sock1.close
sock2.close
end
def test_export_keying_material
start_server do |port|
cli_ctx = OpenSSL::SSL::SSLContext.new
server_connect(port, cli_ctx) do |ssl|
assert_instance_of(String, ssl.export_keying_material('ttls keying material', 64))
assert_operator(64, :==, ssl.export_keying_material('ttls keying material', 64).b.length)
assert_operator(8, :==, ssl.export_keying_material('ttls keying material', 8).b.length)
assert_operator(5, :==, ssl.export_keying_material('test', 5, 'context').b.length)
ssl.puts "abc"; ssl.gets # workaround to make tests work on windows
end
end
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 any of these may be raised
assert_raise(OpenSSL::SSL::SSLError, Errno::ECONNRESET, Errno::EPIPE) {
yield
}
end
end
end