[sans-io] tls tests++

This commit is contained in:
Maximilian Hils 2019-11-23 00:45:31 +01:00
parent 7fbe8cece7
commit 09b6257de0
11 changed files with 328 additions and 17 deletions

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@ -0,0 +1,21 @@
-----BEGIN CERTIFICATE-----
MIIDazCCAlOgAwIBAgIUT0IDh7/Cho/ZPuVDs/jg7g/6+lswDQYJKoZIhvcNAQEL
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-----END CERTIFICATE-----

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@ -0,0 +1,75 @@
"""
Generate SSL test certificates.
"""
import subprocess
import shlex
import os
import shutil
import textwrap
ROOT_CA = "trusted-root"
SUBJECT = "example.mitmproxy.org"
def do(args):
print("> %s" % args)
args = shlex.split(args)
output = subprocess.check_output(args)
return output
def genrsa(cert: str):
do(f"openssl genrsa -out {cert}.key 2048")
def sign(cert: str, subject: str):
with open(f"openssl-{cert}.conf", "w") as f:
f.write(textwrap.dedent(f"""
authorityKeyIdentifier=keyid,issuer
basicConstraints=CA:FALSE
keyUsage = digitalSignature, keyEncipherment
subjectAltName = {subject}
"""))
do(f"openssl x509 -req -in {cert}.csr "
f"-CA {ROOT_CA}.crt "
f"-CAkey {ROOT_CA}.key "
f"-CAcreateserial "
f"-days 7300 "
f"-sha256 "
f"-extfile \"openssl-{cert}.conf\" "
f"-out {cert}.crt"
)
def mkcert(cert, subject):
genrsa(cert)
do(f"openssl req -new -nodes -batch "
f"-key {cert}.key "
f"-addext \"subjectAltName = {subject}\" "
f"-out {cert}.csr"
)
sign(cert, subject)
os.remove(f"{cert}.csr")
# create trusted root CA
genrsa("trusted-root")
do("openssl req -x509 -new -nodes -batch "
"-key trusted-root.key "
"-days 7300 "
"-out trusted-root.crt"
)
h = do("openssl x509 -hash -noout -in trusted-root.crt").decode("ascii").strip()
shutil.copyfile("trusted-root.crt", "{}.0".format(h))
# create trusted leaf cert.
mkcert("trusted-leaf", f'DNS:{SUBJECT}' )
# create self-signed cert
genrsa("self-signed")
do("openssl req -x509 -new -nodes -batch "
"-key self-signed.key "
f'-addext "subjectAltName = DNS:{SUBJECT}" '
"-days 7300 "
"-out self-signed.crt"
)

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@ -0,0 +1,5 @@
authorityKeyIdentifier=keyid,issuer
basicConstraints=CA:FALSE
keyUsage = digitalSignature, keyEncipherment
subjectAltName = DNS:example.mitmproxy.org

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@ -0,0 +1,22 @@
-----BEGIN CERTIFICATE-----
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RA==
-----END CERTIFICATE-----

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@ -0,0 +1,27 @@
-----BEGIN RSA PRIVATE KEY-----
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-----END RSA PRIVATE KEY-----

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@ -0,0 +1,21 @@
-----BEGIN CERTIFICATE-----
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-----END CERTIFICATE-----

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@ -0,0 +1,27 @@
-----BEGIN RSA PRIVATE KEY-----
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-----END RSA PRIVATE KEY-----

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@ -0,0 +1,21 @@
-----BEGIN CERTIFICATE-----
MIIDazCCAlOgAwIBAgIUT0IDh7/Cho/ZPuVDs/jg7g/6+lswDQYJKoZIhvcNAQEL
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-----END CERTIFICATE-----

View File

@ -0,0 +1,27 @@
-----BEGIN RSA PRIVATE KEY-----
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Yz8+xK8M7PUaiVjxrYf8nJ+G61EvglsJ9zeDxKHx7kssi+2xQWeyt0/6yirPtqs9
WdSDeZ9JFa2ah4viStfSqMD47/PpSVHEv9XpE9d+LPww3tLE01W6OBLKHI4JwvO8
Sg5pFwKBgEA0VO9UFijjm6fIARM6Fhdpq0PZDiuPodWrAD3z0C5V6mR4ecgkUIcN
sBvQErzxA9dcUv5D3dPtqP7RIk5+lGfNn0Dqm8Ynr0V018Cojxi6hmmCoXvJNR68
y81DA04Kbo4mjScGxxawN7IfvXRQ5RNPXAuAcw7bEn1RzRlfHiFU
-----END RSA PRIVATE KEY-----

View File

@ -0,0 +1 @@
3E87AEF68CE27F7396C3309503BB595AD9732F3F

View File

@ -69,16 +69,20 @@ class SSLTest:
"""Helper container for Python's builtin SSL object."""
def __init__(self, server_side: bool = False, alpn: typing.Optional[typing.List[str]] = None,
sni: typing.Optional[bytes] = b"example.com"):
sni: typing.Optional[bytes] = b"example.mitmproxy.org"):
self.inc = ssl.MemoryBIO()
self.out = ssl.MemoryBIO()
self.ctx = ssl.SSLContext()
self.ctx = ssl.SSLContext(ssl.PROTOCOL_TLS_SERVER if server_side else ssl.PROTOCOL_TLS_CLIENT)
if alpn:
self.ctx.set_alpn_protocols(alpn)
if server_side:
self.ctx.load_cert_chain(
certfile=tlsdata.path("../../net/data/verificationcerts/trusted-root.crt"),
keyfile=tlsdata.path("../../net/data/verificationcerts/trusted-root.key"),
certfile=tlsdata.path("../../data/verificationcerts/trusted-leaf.crt"),
keyfile=tlsdata.path("../../data/verificationcerts/trusted-leaf.key"),
)
else:
self.ctx.load_verify_locations(
cafile=tlsdata.path("../../data/verificationcerts/trusted-root.crt"),
)
self.obj = self.ctx.wrap_bio(
self.inc,
@ -106,7 +110,9 @@ class TlsEchoLayer(tutils.EchoLayer):
def _handle_event(self, event: events.Event) -> commands.TCommandGenerator:
if isinstance(event, events.DataReceived) and event.data == b"establish-server-tls":
# noinspection PyTypeChecker
self.err = yield tls.EstablishServerTLS(self.context.server)
err = yield tls.EstablishServerTLS(self.context.server)
if err:
yield commands.SendData(event.connection, f"server-tls-failed: {err}".encode())
else:
yield from super()._handle_event(event)
@ -121,7 +127,7 @@ def interact(playbook: tutils.Playbook, conn: context.Connection, tssl: SSLTest)
tssl.inc.write(data())
def reply_tls_start(alpn: typing.Optional[bytes] = None,*args, **kwargs) -> tutils.reply:
def reply_tls_start(alpn: typing.Optional[bytes] = None, *args, **kwargs) -> tutils.reply:
"""
Helper function to simplify the syntax for tls_start hooks.
"""
@ -132,10 +138,14 @@ def reply_tls_start(alpn: typing.Optional[bytes] = None,*args, **kwargs) -> tuti
ssl_context = SSL.Context(SSL.SSLv23_METHOD)
if tls_start.conn == tls_start.context.client:
ssl_context.use_privatekey_file(
tlsdata.path("../../net/data/verificationcerts/trusted-leaf.key")
tlsdata.path("../../data/verificationcerts/trusted-leaf.key")
)
ssl_context.use_certificate_chain_file(
tlsdata.path("../../net/data/verificationcerts/trusted-leaf.crt")
tlsdata.path("../../data/verificationcerts/trusted-leaf.crt")
)
else:
ssl_context.load_verify_locations(
cafile=tlsdata.path("../../data/verificationcerts/trusted-root.crt")
)
if alpn is not None:
if tls_start.conn == tls_start.context.client:
@ -145,6 +155,26 @@ def reply_tls_start(alpn: typing.Optional[bytes] = None,*args, **kwargs) -> tuti
tls_start.ssl_conn = SSL.Connection(ssl_context)
if tls_start.conn != tls_start.context.client:
# Set SNI
tls_start.ssl_conn.set_tlsext_host_name(tls_start.conn.sni)
# Manually enable hostname verification.
# Recent OpenSSL versions provide slightly nicer ways to do this, but they are not exposed in
# cryptography and likely a PITA to add.
# https://wiki.openssl.org/index.php/Hostname_validation
param = SSL._lib.SSL_get0_param(tls_start.ssl_conn._ssl)
# Common Name matching is disabled in both Chrome and Firefox, so we should disable it, too.
# https://www.chromestatus.com/feature/4981025180483584
SSL._lib.X509_VERIFY_PARAM_set_hostflags(
param,
SSL._lib.X509_CHECK_FLAG_NO_PARTIAL_WILDCARDS | SSL._lib.X509_CHECK_FLAG_NEVER_CHECK_SUBJECT
)
SSL._openssl_assert(
SSL._lib.X509_VERIFY_PARAM_set1_host(param, tls_start.conn.sni, 0) == 1
)
SSL._lib.SSL_set_verify(tls_start.ssl_conn._ssl, SSL.VERIFY_PEER, SSL._ffi.NULL)
return tutils.reply(*args, side_effect=make_conn, **kwargs)
@ -167,7 +197,8 @@ class TestServerTLS:
layer = tls.ServerTLSLayer(tctx)
playbook = tutils.Playbook(layer)
tctx.server.connected = True
tctx.server.address = ("example.com", 443)
tctx.server.address = ("example.mitmproxy.org", 443)
tctx.server.sni = b"example.mitmproxy.org"
tssl = SSLTest(server_side=True)
@ -202,6 +233,41 @@ class TestServerTLS:
# Echo
_test_echo(playbook, tssl, tctx.server)
def test_untrusted_cert(self, tctx):
"""If the certificate is not trusted, we should fail."""
layer = tls.ServerTLSLayer(tctx)
playbook = tutils.Playbook(layer)
tctx.server.connected = True
tctx.server.address = ("wrong.host.mitmproxy.org", 443)
tctx.server.sni = b"wrong.host.mitmproxy.org"
tssl = SSLTest(server_side=True)
# send ClientHello
data = tutils.Placeholder()
assert (
playbook
>> events.DataReceived(tctx.client, b"establish-server-tls")
<< commands.Hook("next_layer", tutils.Placeholder())
>> tutils.reply_next_layer(TlsEchoLayer)
<< commands.Hook("tls_start", tutils.Placeholder())
>> reply_tls_start()
<< commands.SendData(tctx.server, data)
)
# receive ServerHello, finish client handshake
tssl.inc.write(data())
with pytest.raises(ssl.SSLWantReadError):
tssl.obj.do_handshake()
assert (
playbook
>> events.DataReceived(tctx.server, tssl.out.read())
<< commands.SendData(tctx.client,
b"server-tls-failed: Error([('SSL routines', 'tls_process_server_certificate', 'certificate verify failed')])")
)
assert not tctx.server.tls_established
def _make_client_tls_layer(tctx: context.Context) -> typing.Tuple[tutils.Playbook, tls.ClientTLSLayer]:
# This is a bit contrived as the client layer expects a server layer as parent.
@ -214,15 +280,13 @@ def _make_client_tls_layer(tctx: context.Context) -> typing.Tuple[tutils.Playboo
return playbook, client_layer
def _test_tls_client_server(
tctx: context.Context,
sni: typing.Optional[bytes] = b"example.com",
alpn: typing.Optional[typing.List[str]] = None
) -> typing.Tuple[tutils.Playbook, tls.ClientTLSLayer, SSLTest]:
def _test_tls_client_server(tctx: context.Context, **kwargs) -> typing.Tuple[
tutils.Playbook, tls.ClientTLSLayer, SSLTest]:
playbook, client_layer = _make_client_tls_layer(tctx)
tctx.server.tls = True
tctx.server.address = ("example.com", 443)
tssl_client = SSLTest(sni=sni, alpn=alpn)
tctx.server.address = ("example.mitmproxy.org", 443)
tctx.server.sni = b"example.mitmproxy.org"
tssl_client = SSLTest(**kwargs)
# Send ClientHello
with pytest.raises(ssl.SSLWantReadError):
@ -296,7 +360,7 @@ class TestClientTLS:
to establish TLS with the client.
"""
tssl_server = SSLTest(server_side=True, alpn=["quux"])
playbook, client_layer, tssl_client = _test_tls_client_server(tctx, sni=None, alpn=["quux"])
playbook, client_layer, tssl_client = _test_tls_client_server(tctx, alpn=["quux"])
# We should now get instructed to open a server connection.
data = tutils.Placeholder()