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[ruby/openssl] Enhance TLS 1.3 support on LibreSSL 3.2/3.3

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This defines TLS1_3_VERSION when using LibreSSL 3.2+.  LibreSSL 3.2/3.3
doesn't advertise this by default, even though it will use TLS 1.3
in both client and server modes.

Changes between LibreSSL 3.1 and 3.2/3.3 broke a few tests, Defining
TLS1_3_VERSION by itself fixes 1 test failure.  A few tests now
fail on LibreSSL 3.2/3.3 unless TLS 1.2 is set as the maximum version,
and this adjusts those tests.  The client CA test doesn't work in
LibreSSL 3.2+, so I've marked that as pending.

For the hostname verification, LibreSSL 3.2.2+ has a new stricter
hostname verifier that doesn't like subjectAltName such as
c*.example.com and d.*.example.com, so adjust the related tests.

With these changes, the tests pass on LibreSSL 3.2/3.3.

https://github.com/ruby/openssl/commit/a0e98d48c9
This commit is contained in:
Jeremy Evans 2020-12-03 09:12:12 -08:00 committed by Kazuki Yamaguchi
parent 4756ac00b7
commit e2ce383044
Notes: git 2021-03-16 20:38:42 +09:00 
Merged: https://github.com/ruby/ruby/pull/4275
5 changed files with 55 additions and 23 deletions
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6
ext/openssl/ossl_ssl.c
View File

@ -13,6 +13,12 @@
#define numberof(ary) (int)(sizeof(ary)/sizeof((ary)[0]))
#if !defined(TLS1_3_VERSION) && \
defined(LIBRESSL_VERSION_NUMBER) && \
LIBRESSL_VERSION_NUMBER >= 0x3020000fL
# define TLS1_3_VERSION 0x0304
#endif
#ifdef _WIN32
# define TO_SOCKET(s) _get_osfhandle(s)
#else

25
test/openssl/test_ssl.rb
View File

@ -306,7 +306,10 @@ class OpenSSL::TestSSL < OpenSSL::SSLTestCase
def test_client_auth_success
vflag = OpenSSL::SSL::VERIFY_PEER|OpenSSL::SSL::VERIFY_FAIL_IF_NO_PEER_CERT
start_server(verify_mode: vflag) { |port|
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
@ -348,6 +351,8 @@ class OpenSSL::TestSSL < OpenSSL::SSLTestCase
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
@ -453,7 +458,11 @@ class OpenSSL::TestSSL < OpenSSL::SSLTestCase
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)
assert_include(
[
OpenSSL::X509::V_ERR_SELF_SIGNED_CERT_IN_CHAIN,
OpenSSL::X509::V_ERR_UNABLE_TO_GET_ISSUER_CERT_LOCALLY
], ssl.verify_result)
ensure
ssl.close
end
@ -523,6 +532,8 @@ class OpenSSL::TestSSL < OpenSSL::SSLTestCase
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
@ -913,11 +924,13 @@ class OpenSSL::TestSSL < OpenSSL::SSLTestCase
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", "DNS:a.example.com,DNS:*.b.example.com," \
"DNS:c*.example.com,DNS:d.*.example.com"],
["subjectAltName", san],
]
ctx.cert = issue_cert(@svr, @svr_key, 4, exts, @ca_cert, @ca_key)
ctx.key = @svr_key
}
@ -939,6 +952,7 @@ class OpenSSL::TestSSL < OpenSSL::SSLTestCase
["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)
@ -1001,7 +1015,7 @@ class OpenSSL::TestSSL < OpenSSL::SSLTestCase
start_server(ignore_listener_error: true) { |port|
ctx = OpenSSL::SSL::SSLContext.new
ctx.set_params
assert_raise_with_message(OpenSSL::SSL::SSLError, /self signed/) {
assert_raise_with_message(OpenSSL::SSL::SSLError, /self signed|unable to get local issuer certificate/) {
server_connect(port, ctx)
}
}
@ -1609,6 +1623,7 @@ end
ctx_proc = -> ctx {
# Enable both ECDHE (~ TLS 1.2) cipher suites and TLS 1.3
ctx.ciphers = "DEFAULT:!kRSA:!kEDH"
ctx.max_version = OpenSSL::SSL::TLS1_2_VERSION if libressl?(3, 2, 0)
ctx.ecdh_curves = "P-384:P-521"
}
start_server(ctx_proc: ctx_proc, ignore_listener_error: true) do |port|

1
test/openssl/test_ssl_session.rb
View File

@ -122,6 +122,7 @@ __EOS__
ctx.options &= ~OpenSSL::SSL::OP_NO_TICKET
# Disable server-side session cache which is enabled by default
ctx.session_cache_mode = OpenSSL::SSL::SSLContext::SESSION_CACHE_OFF
ctx.max_version = OpenSSL::SSL::TLS1_2_VERSION if libressl?(3, 2, 0)
}
start_server(ctx_proc: ctx_proc) do |port|
sess1 = server_connect_with_session(port, nil, nil) { |ssl|

2
test/openssl/test_ts.rb
View File

@ -382,6 +382,7 @@ _end_of_pem_
end
def test_verify_ee_wrong_root_no_intermediate
pend "LibreSSL 3.2.2 Timestamp Issue" if libressl?(3, 2, 2)
assert_raise(OpenSSL::Timestamp::TimestampError) do
ts, req = timestamp_ee
ts.verify(req, intermediate_store)
@ -389,6 +390,7 @@ _end_of_pem_
end
def test_verify_ee_wrong_root_wrong_intermediate
pend "LibreSSL 3.2.2 Timestamp Issue" if libressl?(3, 2, 2)
assert_raise(OpenSSL::Timestamp::TimestampError) do
ts, req = timestamp_ee
ts.verify(req, intermediate_store, [ca_cert])

44
test/openssl/test_x509store.rb
View File

@ -32,15 +32,17 @@ class OpenSSL::TestX509Store < OpenSSL::TestCase
assert_equal true, store.verify(cert1)
assert_equal true, store.verify(cert2)
# X509::Store#add_path
Dir.mktmpdir do |dir|
hash1 = "%08x.%d" % [cert1_subj.hash, 0]
File.write(File.join(dir, hash1), cert1.to_pem)
store = OpenSSL::X509::Store.new
store.add_path(dir)
unless libressl?(3, 2, 2)
# X509::Store#add_path
Dir.mktmpdir do |dir|
hash1 = "%08x.%d" % [cert1_subj.hash, 0]
File.write(File.join(dir, hash1), cert1.to_pem)
store = OpenSSL::X509::Store.new
store.add_path(dir)
assert_equal true, store.verify(cert1)
assert_equal false, store.verify(cert2)
assert_equal true, store.verify(cert1)
assert_equal false, store.verify(cert2)
end
end
# OpenSSL < 1.1.1 leaks an error on a duplicate certificate
@ -75,8 +77,8 @@ class OpenSSL::TestX509Store < OpenSSL::TestCase
# Nothing trusted
store = OpenSSL::X509::Store.new
assert_equal(false, store.verify(ee1_cert, [ca2_cert, ca1_cert]))
assert_equal(OpenSSL::X509::V_ERR_SELF_SIGNED_CERT_IN_CHAIN, store.error)
assert_match(/self.signed/i, store.error_string)
assert_include([OpenSSL::X509::V_ERR_SELF_SIGNED_CERT_IN_CHAIN, OpenSSL::X509::V_ERR_UNABLE_TO_GET_ISSUER_CERT_LOCALLY], store.error)
assert_match(/self.signed|unable to get local issuer certificate/i, store.error_string)
# CA1 trusted, CA2 missing
store = OpenSSL::X509::Store.new
@ -121,10 +123,11 @@ class OpenSSL::TestX509Store < OpenSSL::TestCase
}
store.add_cert(ca1_cert)
assert_equal(true, store.verify(ee1_cert, [ca2_cert]))
assert_equal(3, cb_calls.size)
assert_equal([true, ca1_cert], cb_calls[0])
assert_equal([true, ca2_cert], cb_calls[1])
assert_equal([true, ee1_cert], cb_calls[2])
assert_include([2, 3, 4, 5], cb_calls.size)
cb_calls.each do |pre_ok, cert|
assert_equal(true, pre_ok)
assert_include([ca1_cert, ca2_cert, ee1_cert], cert)
end
# verify_callback can change verification result
store = OpenSSL::X509::Store.new
@ -185,7 +188,7 @@ class OpenSSL::TestX509Store < OpenSSL::TestCase
store.purpose = OpenSSL::X509::PURPOSE_CRL_SIGN
store.add_cert(ca1_cert)
assert_equal(true, store.verify(ca1_cert))
assert_equal(false, store.verify(ee1_cert))
assert_equal(libressl?(3, 2, 2), store.verify(ee1_cert))
end
def test_verify_validity_period
@ -281,7 +284,7 @@ class OpenSSL::TestX509Store < OpenSSL::TestCase
store.flags = OpenSSL::X509::V_FLAG_CRL_CHECK
store.add_cert(ca1_cert)
assert_equal(false, store.verify(ca2_cert))
assert_equal(OpenSSL::X509::V_ERR_UNABLE_TO_GET_CRL, store.error)
assert_include([OpenSSL::X509::V_ERR_UNABLE_TO_GET_CRL, OpenSSL::X509::V_ERR_UNSPECIFIED], store.error)
# Intermediate CA revoked EE2
store = OpenSSL::X509::Store.new
@ -321,9 +324,14 @@ class OpenSSL::TestX509Store < OpenSSL::TestCase
store.add_cert(ca2_cert)
store.add_crl(ca1_crl1)
store.add_crl(ca2_crl2) # issued by ca2 but expired
assert_equal(true, store.verify(ca2_cert))
if libressl?(3, 2, 2)
assert_equal(false, store.verify(ca2_cert))
assert_include([OpenSSL::X509::V_ERR_CRL_SIGNATURE_FAILURE, OpenSSL::X509::V_ERR_UNSPECIFIED], store.error)
else
assert_equal(true, store.verify(ca2_cert))
end
assert_equal(false, store.verify(ee1_cert))
assert_equal(OpenSSL::X509::V_ERR_CRL_HAS_EXPIRED, store.error)
assert_include([OpenSSL::X509::V_ERR_CRL_HAS_EXPIRED, OpenSSL::X509::V_ERR_UNSPECIFIED], store.error)
assert_equal(false, store.verify(ee2_cert))
end