[Bug 1899878] Re: Python's test_ssl fails starting from Ubuntu 20.04

2021-03-12 Thread Dimitri John Ledkov
On SSLcontext, security callback has prototype

/* Security callback */
int (*sec_cb) (const SSL *s, const SSL_CTX *ctx, int op, int bits, int nid,
   void *other, void *ex);

if one calls that function, with context passed in, "op" set to
SSL_SECOP_VERSION, "bits" set to zero, "nid" set to protocol version,
other set to NULL, and ex set to null => then the security callback will
tell us if at the current configuration a given protocol version is
acceptable.

This should work on OpenSSL 1.1.0+

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[Bug 1899878] Re: Python's test_ssl fails starting from Ubuntu 20.04

2021-03-12 Thread Marc Deslauriers
I've read through this bug and I don't see a good way forward with a
solution here. OpenSSL 1.1.1 doesn't provide the exact API that is
required to solve it, which would probably be 3) as suggested above, but
I don't think Ubuntu should change the meaning of the value returned by
that API.

Ubuntu is returning the value that is expected of the upstream 1.1.1
code when security levels are used.

While Ubuntu, Debian, and Fedora use different approaches to achieve a
similar goal, and Ubuntu did modify the meaning of security level 2 to
restrict it further than the upstream default, the fact remains that
building OpenSSL with a higher default security level results in a
situation where there seems to be no good API to request what the
minimum TLS version is.

It may appear reasonable that a simple query to the current security
level could have given a hardcoded indication of what is available.
Unfortunately, that assumption doesn't stand the test of time as it is
no longer valid once the security levels have been modified to align
with the current best practices, either in a new OpenSSL release, or by
a distro.

This is a less than ideal situation, but I think the only way forward
currently available when obsolete TLS versions need to be used is to set
the minimum security level accepted by OpenSSL.

We should work with upstream OpenSSL to make sure 3.0 provides the right
APIs, documentation, and guidance that are required to handle changing
defaults like this more elegantly in the future.

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[Bug 1899878] Re: Python's test_ssl fails starting from Ubuntu 20.04

2021-03-10 Thread Kurt Roeckx
2) and 3) would never return 0, which is what the upstream OpenSSL
version returns now.

2) would make it return TLS1_VERSION for the minimum and TLS1_3_VERSION
for the maximum with default build options. If you enable SSlv3 support
at compile time, the minimum would return SSL3_VERSION. Note that there
is a TLS_MAX_VERSION define that's equal to TLS1_3_VERSION, but no such
define for the minimum.

1) would just return what is set, which is 0 upstream and for Ubuntu for
both minimum and maximum, where 0 is defined as no limit set. Debian
sets the minimum to TLS1_2_VERSION, and so returns that value. But maybe
if no limit is set (and so the value is 0), it can instead return the
minimum/maximum version that's supported at compile time.

3) Would have as effect that upstream in 1.1.1 returns TLS1_VERSION and
TLS1_3_VERSION, but TLS1_2_VERSION and TLS1_3_VERSION in 3.0. For Ubuntu
and Debian it would return TLS1_2_VERSION and TLS1_3_VERISON, since that
is what they do using a different method.

Setting the default minimum to TLS1_2_VERSION (at compile time) will
clearly fix your problem. But I think you're going to run in the same
problem with 3.0, and we should probably add a new API in 3.0 for it.

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[Bug 1899878] Re: Python's test_ssl fails starting from Ubuntu 20.04

2021-03-10 Thread Christian Heimes
In upstream OpenSSL, (3) is the same as (1) for a pristine
SSL_CTX_new(TLS_method()) context.

As far as I can see, the Ubuntu patch effectively sets the minimum
version to TLS 1.2 and prevents users from setting TLS 1.0 and 1.1. I
propose that the patch also changes the value of minimum protocol on the
CTX, so (1) reports TLS1_2_VERSION as current value.

OpenSSL upstream is not going to accept a new function into 1.1.1 LTS
branch.

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[Bug 1899878] Re: Python's test_ssl fails starting from Ubuntu 20.04

2021-03-09 Thread Kurt Roeckx
There are 3 things that can possibly returned by such a function:
1) The value that's set as minimum/maximum
2) The minimum and maximum version that's supported by the library, not 
depending on settings
3) The minimum and maximum version that's supported by the library, depending 
on current settings

The function now does 1), and you seem to want 3). And I'm not sure it's
a good idea to change the function, I would prefer a new function.

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[Bug 1899878] Re: Python's test_ssl fails starting from Ubuntu 20.04

2021-03-09 Thread Christian Heimes
Actually, I don't want to enable TLS 1.0 and 1.1 when these versions are
disabled by crypto policy or openssl.cnf. It's totally ok that these
versions are disabled and don't work any more! I just need a reliable
way to *detect* that the versions are disabled at runtime.

The feature detection logic boils down to this pseudo code:

min_version = SSL_CTX_get_min_proto_version(ctx)
if not defined(TLS1_VERSION) or defined(OPENSSL_NO_TLS1):
return False
elif min_version == 0 or min_version >= TLS1_VERSION:
return True
else:
return False

On Debian, SSL_CTX_get_min_proto_version() returns TLS1_2_VERSION and
Python considers TLS 1.0 and 1.1 as disabled by system policy. All test
cases for TLS 1.0 and TLS 1.1 are skipped.

Ubuntu has TLS1_VERSION defined, OPENSSL_NO_TLS1 not defined, and
SSL_CTX_get_min_proto_version() returns 0. So Python assumes that TLS
1.0 is compiled in, supported, and enabled. But it's actually disabled
and tests are failing.

I completely agree with your comment 13: 0 is not a good return value.
Could you modify Ubuntu's patch so that
SSL_CTX_get_min_proto_version(ctx) returns TLS1_2_VERSION and
SSL_CTX_set_min_proto_version(ctx, TLS1_VERSION) returns an error? This
would fix Python's problem.

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[Bug 1899878] Re: Python's test_ssl fails starting from Ubuntu 20.04

2021-03-06 Thread Kurt Roeckx
My understanding of things is that Ubuntu does this:
- Set the default security level to 2 (at compile time)
- Disable TLS 1.0 and 1.1 at security level 2, only keeping TLS 1.2 by default

This is what Debian does:
- Set the default security level to 2 (using a config file)
- Set the minimum version to TLS 1.2 (using a config file)

To be able to use TLS 1.0 on Ubuntu you need to:
- Change the security level to 1

To be able to use TLS 1.0 on Debian you need to:
- Set the minimum allowed version to TLS 1.0

My understanding of the issue is that python doesn't know which TLS
version can be negotiated, and uses or overrides the minimum TLS version
which happens to currently work on Debian. But for the test suite it
should also override the security level.

Note that in upstream OpenSSL 3.0, TLS 1.0 and 1.1 no longer meet the
requirements for security level 1, if you want to use TLS 1.0 in the
test suite you need to set the security level to 0.

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[Bug 1899878] Re: Python's test_ssl fails starting from Ubuntu 20.04

2021-03-06 Thread Kurt Roeckx
I was expecting SSL_CTX_get_min_proto_version() to return the default
value (TLS1_2_VERSION). It's currently documented that 0 means the
lowest supported by the library. If it returns 0 and the library
supports TLS 1.0, it should be able to negotiate TLS 1.0.

On reflection, I'm not sure that for the get function 0 is ever a good
value to return, it should always return a version.

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[Bug 1899878] Re: Python's test_ssl fails starting from Ubuntu 20.04

2021-03-03 Thread Christian Heimes
> I'm not sure how this is related to anything of the above, can you
please open a new bug report with details?

It looks like both issues are caused by the same patch. I have filed
https://bugs.launchpad.net/ubuntu/+source/openssl/+bug/1917625 for the
internal error message and uploaded a Dockerfiles with a reproducer.

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[Bug 1899878] Re: Python's test_ssl fails starting from Ubuntu 20.04

2021-03-03 Thread Christian Heimes
(Short answer, I'm in meetings for the rest of the day)

Python's ssl module doesn't support TLS over UDP. DTLS is not an issue
for CPython. I have limited experience with DTLS and cannot contribute
much to that part of the discussion. Python's test suite uses its own
set of certificates for testing. We don't rely on system's CA store. All
certs and DH parameters are chosen to work on security level 2. (I've
been bitten by old settings when I made Python core and tests FIPS
compliant.)

Does Ubuntu's OpenSSL 1.0.x compat package use the same config file as
OpenSSL 1.1.1? I can see how that can cause trouble. Fedora's compat-
openssl10 package works around incompatible config files by using
openssl10.cnf instead of openssl.cnf with patch
https://src.fedoraproject.org/rpms/compat-
openssl10/blob/f33/f/openssl-1.0.2o-conf-10.patch.

If you get SSL_CTX_get_min_proto_version() to return TLS1_2_VERSION,
then we can detect the minimum version in Python. The macro currently
returns "0" on Ubuntu. Python then falls back to "#if
defined(TLS1_VERSION) && !defined(OPENSSL_NO_TLS1)" to detect if TLS 1.0
is available.
https://github.com/python/cpython/blob/b04f1cb9df7ad93366ef0ef7d8088effc576c5ae/Lib/test/test_ssl.py#L155-L210

>>> import ssl
>>> ctx = ssl.create_default_context()
>>> ctx.minimum_version



A reproducer for the "internal error" during handshake is:

def test_min_max_version_tlsv1_1(self):
client_context, server_context, hostname = testing_context()
# client 1.0 to 1.2, server 1.0 to 1.1
client_context.minimum_version = ssl.TLSVersion.TLSv1
client_context.maximum_version = ssl.TLSVersion.TLSv1_2
server_context.minimum_version = ssl.TLSVersion.TLSv1
server_context.maximum_version = ssl.TLSVersion.TLSv1_1

with ThreadedEchoServer(context=server_context) as server:
with client_context.wrap_socket(socket.socket(),
server_hostname=hostname) as s:
s.connect((HOST, server.port))
self.assertEqual(s.version(), 'TLSv1.1')

I'll try to find some time to create a new report.

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[Bug 1899878] Re: Python's test_ssl fails starting from Ubuntu 20.04

2021-03-03 Thread Marc Deslauriers
Please disregard comment #9, this is a different issue.

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[Bug 1899878] Re: Python's test_ssl fails starting from Ubuntu 20.04

2021-03-03 Thread Marc Deslauriers
The python2.7 security updates that will be released today will fix this
issue.

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[Bug 1899878] Re: Python's test_ssl fails starting from Ubuntu 20.04

2021-03-03 Thread Dimitri John Ledkov
But Debian & Fedora implementation are buggy, because they break 1.0.2x
users & they do not prohibit DTLSv1.1 whilst enforcing TLSv1.2+.

So although Debian & Fedora look "nice" they are security vulnerable
configurations.

I can set min_version to TLSv1.2, in addition to security level 2 but
that will not make current stable test_ssl test suite pass, as it will
require not only changing min_level but also setting security level to
1.

I do not see a way to make things secure, for both TLS and DTLS, and
discoverable and not pain to use. Because when default context is
created it is not known if TLS or DTLS will be used, and the enums for
TLS & DTLS are not compatible with each other.

Ultimately it is deficiency in the OpenSSL APIs because it is impossible
to know what is or isn't allowed by a given client OpenSSL context,
against which server context, and vice versa. Even when enums are
available, and one sets them as appropriate min/max. There are no
inspection APIs available into the security levels. For example, it
impossible to query if ones client certificate is suitable for a given
security level, apart from trying to establish the connection.

Re Kurt => i have spoken to Kurt about this, he is aware that Debian's
implementation is buggy and he does prefer Ubuntu's one, however
Ubuntu's one is not without drawbacks either. I.e. at the moment in
Debian people simply choose to not install openssl package and thus end
up operating without public certificates and with TLS v1.1/v1.0 enabled,
meaning the system is insecure by accident against the intentions.
Especially if one tries to be secure, and use private CA certificates
only.


"""
2) With some configuration, OpenSSL's SSL_do_handshake() function fails with an 
"internal error" message (SSL_AD_INTERNAL_ERROR / TLS1_AD_INTERNAL_ERROR) 
somewhere in its internal state machine.
""" 

I'm not sure how this is related to anything of the above, can you
please open a new bug report with details? crashes in handshake are
typically specific to the connection type, context on both client &
server, and well bugs. The one thing that I know failing badly, is when
server has redundant tls certificates in its chain that are considered
insecured (i.e. old CA cross-signed new CA). And OpenSSL client
currently rejects establishing the connection, despite the server chain
having alternative paths of certs that are secure throughout.

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[Bug 1899878] Re: Python's test_ssl fails starting from Ubuntu 20.04

2021-03-03 Thread Christian Heimes
CC Kurt Roeckx

Kurt, could you please take a look? An Ubuntu's downstream patch for
OpenSSL causes TLS1_AD_INTERNAL_ERROR internal error in OpenSSL's state
machine and breaks CPython's test suite. Debian is not affected. It's
the same problem I mentioned in my gist a couple of months ago.

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[Bug 1899878] Re: Python's test_ssl fails starting from Ubuntu 20.04

2021-03-03 Thread Christian Heimes
PS: Ultimately it is your call how you want to handle the issue. You can
either treat it as a bug in Ubuntu's downstream patch or close the issue
as WONTFIX. In the latter case I'll add some hacks to our test suite and
update our documentation that some legacy TLS features are not working
on Ubuntu. I would appreciate if you fix the underlying issue, though.
An internal error in the TLS state machine sounds troubling.

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[Bug 1899878] Re: Python's test_ssl fails starting from Ubuntu 20.04

2021-03-03 Thread Christian Heimes
This is really just a problem with Ubuntu 20.04 and 20.10 (and maybe
older/newer releases). The same tests are passing fine on latest Debian
testing as well as Fedora. Debian testing and Fedora use a crypto policy
that raises security level to 2 and disallows TLS 1.0 and 1.1. Python's
test suite introspects OpenSSL settings and skips tests of disabled TLS
versions.

There seems to be a major difference between Debian and Ubuntu's
downstream patches of OpenSSL. Ubuntu's patch causes two problems

1) Python cannot figure out that TLS 1.0 and 1.1 are disabled on Ubuntu. The 
same code works fine on Debian and Fedora.
2) With some configuration, OpenSSL's SSL_do_handshake() function fails with an 
"internal error" message (SSL_AD_INTERNAL_ERROR / TLS1_AD_INTERNAL_ERROR) 
somewhere in its internal state machine.

I suggest that you involve Kurt and look at the difference between
Debian's downstream patch and Ubuntu's downstream patch.

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[Bug 1899878] Re: Python's test_ssl fails starting from Ubuntu 20.04

2021-03-03 Thread Dimitri John Ledkov
Fedora & Debian & Ubuntu implement openssl differently.

In Ubuntu, as an Ubuntu-specific patch, we set default security level to
2, and prohibit protocols lower than TLSv1.2 / DTLSv1.2.

This is documented in the Ubuntu manpages for OpenSSL

http://manpages.ubuntu.com/manpages/hirsute/en/man3/SSL_CTX_set_security_level.3ssl.html

"""
The default security level can be configured when OpenSSL is compiled by 
setting -DOPENSSL_TLS_SECURITY_LEVEL=level. On Ubuntu, 2 is used.

Level 2
   Security level set to 112 bits of security. As a result RSA, DSA and DH keys 
shorter
   than 2048 bits and ECC keys shorter than 224 bits are prohibited.  In 
addition to the
   level 1 exclusions any cipher suite using RC4 is also prohibited. On Ubuntu, 
TLS
   versions below 1.2 are not permitted. Compression is disabled.
"""

This is the only way that we have able to configure minimum key sizes,
protocol versions for both TLS and DTLS without making any openssl cnf
changes, whilst remaining compatible with both openssl cnf from 1.0.2x,
1.1.0x and 1.1.1x series. As min/max API calls are not available across
all openssl series and software that allows to configure openssl
cipherstrings but not min/max versions.

If you need access to (D)TLS below 1.2  or weak cryptography you can use
openssl 1.1.1 API to set_security level to 1. Or you can set
CipherString to DEFAULT@SECLEVEL=1. Without modifying the software at
all, libssl can be configured via envrionment variables too.

I.e. exporting

export OPENSSL_CONF=`pwd`/openssl.cnf
cat openssl.cnf
openssl_conf = default_conf
[default_conf]
ssl_conf = ssl_sect
[ssl_sect]
system_default = system_default_sect
[system_default_sect]
CipherString = DEFAULT@SECLEVEL=1

Note that this openssl.cnf is compatible with _any_ openssl series.

In debian, they set min versions of TLS communication only, which breaks
with openssl 1.0.2x series as it fails to parse those settings. That was
unacceptable for Ubuntu.

I don't know how Fedora implements this, I guess I should take a look.

It would be nice for OpenSSL upstream to provide a standard configure
time option to set these things in a consistent manner, as at the moment
each distribution has to invent their own way of doing this. My
proposals to bump minimum protocol versions to TLSv1.2 in OpenSSL 3.0.0
for the time being got rejected, as it is deemed too soon.

In Ubuntu, we also configure GnuTLS with similar parameters, the
override mechanism there is different see https://discourse.ubuntu.com/t
/default-to-tls-v1-2-in-all-tls-libraries-in-20-04-lts/12464/8 for both
OpenSSL and GnuTLS details.

I'm not sure what is expected from this bug report. Ubuntu changes are
documented and publicized and are trivial to find. Were you expecting to
find this documentation somewhere else? Where did you look? I am happy
to add more documentation in more places, or change the implementation.

What does Fedora do? And is it portable to distributions that do not use
the crypto-policies package to maintain configs?

** Changed in: openssl (Ubuntu)
   Status: Confirmed => Incomplete

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[Bug 1899878] Re: Python's test_ssl fails starting from Ubuntu 20.04

2021-03-02 Thread Christian Heimes
FYI, yesterday GitHub Actions moved "ubuntu-latest" to 20.04. This
caused breakage in CPython's CI, https://bugs.python.org/issue43382

** Bug watch added: Python Roundup #43382
   http://bugs.python.org/issue43382

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[Bug 1899878] Re: Python's test_ssl fails starting from Ubuntu 20.04

2020-10-15 Thread Launchpad Bug Tracker
Status changed to 'Confirmed' because the bug affects multiple users.

** Changed in: openssl (Ubuntu)
   Status: New => Confirmed

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[Bug 1899878] Re: Python's test_ssl fails starting from Ubuntu 20.04

2020-10-14 Thread Bug Reporter
Sorry, this is the correct link:
https://bugs.python.org/issue41561#msg378103

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