self-signed.pythontest.net TLS certificate key is too weak #80997

gpshead · 2019-05-06T18:05:41Z

BPO	36816
Nosy	@gpshead, @larryhastings, @ned-deily, @aixtools, @yan12125, @ewdurbin, @miss-islington
PRs	bpo-35925: Skip SSL tests that fail due to weak external certs. #13124 bpo-36816: Update the self-signed.pythontest.net cert #13192 [3.7] bpo-36816: Update the self-signed.pythontest.net cert (GH-13192) #13197 [3.6] bpo-36816: Update the self-signed.pythontest.net cert (GH-13192) #13198 [2.7] bpo-36816: Update the self-signed.pythontest.net cert (GH-13192) #13199 [3.5] bpo-36816: Update the self-signed.pythontest.net cert (GH-13192) #13200

^{Note: these values reflect the state of the issue at the time it was migrated and might not reflect the current state.}

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GitHub fields:

assignee = 'https://github.com/gpshead'
closed_at = <Date 2019-09-09.09:39:04.028>
created_at = <Date 2019-05-06.18:05:40.595>
labels = ['3.7', 'expert-SSL', '3.8', 'type-bug', 'tests']
title = 'self-signed.pythontest.net TLS certificate key is too weak'
updated_at = <Date 2019-09-09.09:39:04.027>
user = 'https://github.com/gpshead'

bugs.python.org fields:

activity = <Date 2019-09-09.09:39:04.027>
actor = 'gregory.p.smith'
assignee = 'gregory.p.smith'
closed = True
closed_date = <Date 2019-09-09.09:39:04.028>
closer = 'gregory.p.smith'
components = ['Tests', 'SSL']
creation = <Date 2019-05-06.18:05:40.595>
creator = 'gregory.p.smith'
dependencies = []
files = []
hgrepos = []
issue_num = 36816
keywords = ['patch']
message_count = 15.0
messages = ['341579', '341590', '341843', '341865', '341866', '341908', '341931', '341946', '341950', '342988', '342997', '343020', '343027', '347841', '351382']
nosy_count = 7.0
nosy_names = ['gregory.p.smith', 'larry', 'ned.deily', 'Michael.Felt', 'yan12125', 'EWDurbin', 'miss-islington']
pr_nums = ['13124', '13192', '13197', '13198', '13199', '13200']
priority = 'normal'
resolution = 'remind'
stage = 'resolved'
status = 'closed'
superseder = None
type = 'behavior'
url = 'https://bugs.python.org/issue36816'
versions = ['Python 2.7', 'Python 3.5', 'Python 3.6', 'Python 3.7', 'Python 3.8']

gpshead · 2019-05-06T18:05:40Z

test_httplib uses self-signed.pythontest.net in it's test_networked_good_cert test.

On modern Linux distros (current Debian testing sid), the certificate it currently uses is rightfully rejected as being too weak:

ERROR: test_networked_good_cert (test.test_httplib.HTTPSTest)
----------------------------------------------------------------------

Traceback (most recent call last):
  File "/home/greg/oss/cpython/Lib/test/test_httplib.py", line 1628, in test_networked_good_cert
    h.request('GET', '/')
  File "/home/greg/oss/cpython/Lib/http/client.py", line 1221, in request
    self._send_request(method, url, body, headers, encode_chunked)
  File "/home/greg/oss/cpython/Lib/http/client.py", line 1267, in _send_request
    self.endheaders(body, encode_chunked=encode_chunked)
  File "/home/greg/oss/cpython/Lib/http/client.py", line 1216, in endheaders
    self._send_output(message_body, encode_chunked=encode_chunked)
  File "/home/greg/oss/cpython/Lib/http/client.py", line 1004, in _send_output
    self.send(msg)
  File "/home/greg/oss/cpython/Lib/http/client.py", line 944, in send
    self.connect()
  File "/home/greg/oss/cpython/Lib/http/client.py", line 1383, in connect
    self.sock = self._context.wrap_socket(self.sock,
  File "/home/greg/oss/cpython/Lib/ssl.py", line 405, in wrap_socket
    return self.sslsocket_class._create(
  File "/home/greg/oss/cpython/Lib/ssl.py", line 853, in _create
    self.do_handshake()
  File "/home/greg/oss/cpython/Lib/ssl.py", line 1117, in do_handshake
    self._sslobj.do_handshake()
ssl.SSLCertVerificationError: [SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed: EE certificate key too weak (_ssl.c:1055)

The TLS certificate on the server needs to be updated to something modern. I _believe_ this can be done by someone with infrastructure access via an update to https://github.com/python/pythontestdotnet/tree/master/tls

Assigning to EWDurbin for triage and redirection to someone else infrastructury if he's not the right person.

How to know if it has been fixed? Monitor the test_networked_good_cert test on any "Debian buster" builtbot(s) such as https://buildbot.python.org/all/#/workers/23 to make sure it is not skipped. (the test _currently_ fails, I am going to have it be _skipped_ on this specific key too small error for the time being to get that stable buildbot green again)

gpshead · 2019-05-06T18:36:32Z

EWDurbin says I can just open a PR with new certs in the repo and it'll go from there. :)

gpshead · 2019-05-08T01:27:02Z

Updated cert+key committed to pythontestdotnet. reassigning to EWDurbin to see that they're deployed.

python/pythontestdotnet@2d12141

ewdurbin · 2019-05-08T11:18:49Z

Cert updated, reassigning back to gregory.p.smith to verify and close this out.

yan12125 · 2019-05-08T11:53:47Z

Lib/test/selfsigned_pythontestdotnet.pem in the cpython repository needs to be updated to match https://github.com/python/pythontestdotnet/blob/master/tls/self-signed-cert.pem, or the test fails :)

======================================================================
ERROR: test_networked_good_cert (test.test_httplib.HTTPSTest)
----------------------------------------------------------------------

Traceback (most recent call last):
  File "/home/yen/tmp/cpython/Lib/test/test_httplib.py", line 1632, in test_networked_good_cert
    h.request('GET', '/')
  File "/home/yen/tmp/cpython/Lib/http/client.py", line 1221, in request
    self._send_request(method, url, body, headers, encode_chunked)
  File "/home/yen/tmp/cpython/Lib/http/client.py", line 1267, in _send_request
    self.endheaders(body, encode_chunked=encode_chunked)
  File "/home/yen/tmp/cpython/Lib/http/client.py", line 1216, in endheaders
    self._send_output(message_body, encode_chunked=encode_chunked)
  File "/home/yen/tmp/cpython/Lib/http/client.py", line 1004, in _send_output
    self.send(msg)
  File "/home/yen/tmp/cpython/Lib/http/client.py", line 944, in send
    self.connect()
  File "/home/yen/tmp/cpython/Lib/http/client.py", line 1383, in connect
    self.sock = self._context.wrap_socket(self.sock,
  File "/home/yen/tmp/cpython/Lib/ssl.py", line 405, in wrap_socket
    return self.sslsocket_class._create(
  File "/home/yen/tmp/cpython/Lib/ssl.py", line 853, in _create
    self.do_handshake()
  File "/home/yen/tmp/cpython/Lib/ssl.py", line 1117, in do_handshake
    self._sslobj.do_handshake()
ssl.SSLCertVerificationError: [SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed: self signed certificate (_ssl.c:1055)

miss-islington · 2019-05-08T16:35:13Z

New changeset 6bd8173 by Miss Islington (bot) (Gregory P. Smith) in branch 'master':
bpo-36816: Update the self-signed.pythontest.net cert (GH-13192)
6bd8173

ned-deily · 2019-05-08T19:21:05Z

New changeset 2b9d7ab by Ned Deily (Gregory P. Smith) in branch '3.6':
[3.6] bpo-36816: Update the self-signed.pythontest.net cert (GH-13192) (GH-13198)
2b9d7ab

miss-islington · 2019-05-08T21:13:13Z

New changeset 6daaf3f by Miss Islington (bot) (Gregory P. Smith) in branch '3.7':
[3.7] bpo-36816: Update the self-signed.pythontest.net cert (GH-13192) (GH-13197)
6daaf3f

gpshead · 2019-05-09T00:53:25Z

New changeset 7b5dca8 by Gregory P. Smith in branch '2.7':
[2.7] bpo-36816: Update the self-signed.pythontest.net cert (GH-13192) (GH-13199)
7b5dca8

aixtools · 2019-05-21T09:09:51Z

I am not an OpenSSL expert - and I am conscious of OpenSSL changes with regard to 'acceptance' of anything self-signed.

And, what it looks like you are trying to do with an updated 'signing" .pem is to remove the 'self-signed' charasteric.

On AIX - atm - I get, as did Chih-Hsuan Yen (yan12125),

======================================================================
ERROR: test_networked_good_cert (test.test_httplib.HTTPSTest)
----------------------------------------------------------------------

Traceback (most recent call last):
  File "/home/buildbot/python-master/Lib/test/test_httplib.py", line 1632, in test_networked_good_cert
    h.request('GET', '/')
  File "/home/buildbot/python-master/Lib/http/client.py", line 1221, in request
    self._send_request(method, url, body, headers, encode_chunked)
  File "/home/buildbot/python-master/Lib/http/client.py", line 1267, in _send_request
    self.endheaders(body, encode_chunked=encode_chunked)
  File "/home/buildbot/python-master/Lib/http/client.py", line 1216, in endheaders
    self._send_output(message_body, encode_chunked=encode_chunked)
  File "/home/buildbot/python-master/Lib/http/client.py", line 1004, in _send_output
    self.send(msg)
  File "/home/buildbot/python-master/Lib/http/client.py", line 944, in send
    self.connect()
  File "/home/buildbot/python-master/Lib/http/client.py", line 1383, in connect
    self.sock = self._context.wrap_socket(self.sock,
  File "/home/buildbot/python-master/Lib/ssl.py", line 405, in wrap_socket
    return self.sslsocket_class._create(
  File "/home/buildbot/python-master/Lib/ssl.py", line 853, in _create
    self.do_handshake()
  File "/home/buildbot/python-master/Lib/ssl.py", line 1117, in do_handshake
    self._sslobj.do_handshake()
ssl.SSLCertVerificationError: [SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed: self signed certificate (_ssl.c:1055)

And I see why now:
test_networked_good_cert (test.test_httplib.HTTPSTest) ... skipped "Use of the 'network' resource not enabled"

Digging a bit:

buildbot@x064:[/home/buildbot/python-master]openssl s_client -connect self-signed.pythontest.net:443
CONNECTED(00000003)
depth=0 C = XY, ST = Castle Anthrax, L = Argument Clinic, O = Python Software Foundation, CN = self-signed.pythontest.net
verify error:num=18:self signed certificate
verify return:1
depth=0 C = XY, ST = Castle Anthrax, L = Argument Clinic, O = Python Software Foundation, CN = self-signed.pythontest.net
verify return:1
---
Certificate chain
0 s:/C=XY/ST=Castle Anthrax/L=Argument Clinic/O=Python Software Foundation/CN=self-signed.pythontest.net

i:/C=XY/ST=Castle Anthrax/L=Argument Clinic/O=Python Software Foundation/CN=self-signed.pythontest.net

And while this:
How to know if it has been fixed? Monitor the test_networked_good_cert test on any "Debian buster" builtbot(s) such as https://buildbot.python.org/all/#/workers/23 to make sure it is not skipped. (the test _currently_ fails, I am going to have it be _skipped_ on this specific key too small error for the time being to get that stable buildbot green again)

is nice for some, it is not nice for all!

Perhaps the test should be switched to 'warn' on failure, rather than error on failure, until fixed!

aixtools · 2019-05-21T10:08:30Z

p.s. On Centos I could not even get a python3 (at least not easily).

On debian (on POWER) I get the same error (message) as on AIX - although the line number did change.

ssl.SSLCertVerificationError: [SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed: self signed certificate (_ssl.c:1056)

so, not a message about "key too small error" - pure, this is self-signed, so error.

aixtools · 2019-05-21T12:00:14Z

On 21/05/2019 12:08, Michael Felt wrote:

Michael Felt <aixtools@felt.demon.nl> added the comment:

p.s. On Centos I could not even get a python3 (at least not easily).

On debian (on POWER) I get the same error (message) as on AIX - although the line number did change.

ssl.SSLCertVerificationError: [SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed: self signed certificate (_ssl.c:1056)

so, not a message about "key too small error" - pure, this is self-signed, so error.

----------
p.s. blush: seems I was testing against the wrong fork - seems to be
cleared in 'master'. My apologies for the noise.

Python tracker <report@bugs.python.org>
<https://bugs.python.org/issue36816\>

yan12125 · 2019-05-21T12:12:21Z

Hi Michael Felt,

And, what it looks like you are trying to do with an updated 'signing" .pem is to remove the 'self-signed' charasteric.

If I understand it correctly, the new certificate is indeed still self-signed. It's updated to match the certificate deployed at https://self-signed.pythontest.net/. Under the hood load_verify_locations() at line 1628 is used to make the test accept any valid certificate signed with the given certificate.

As a record, with CPython e7cb23b and OpenSSL 1.1.1b on Arch Linux x86_64, the test is green:

test_networked_good_cert (test.test_httplib.HTTPSTest) ... ok

By the way, I believe the "key too weak" workaround can be removed now and then this issue can be closed.

larryhastings · 2019-07-13T15:35:40Z

New changeset 221178a by larryhastings (Gregory P. Smith) in branch '3.5':
[3.5] bpo-36816: Update the self-signed.pythontest.net cert (GH-13192) (bpo-13200)
221178a

gpshead · 2019-09-09T09:39:04Z

I believe this has been addressed.

gpshead assigned ewdurbin May 6, 2019

gpshead added 3.7 (EOL) end of life 3.8 (EOL) end of life tests Tests in the Lib/test dir topic-SSL type-bug An unexpected behavior, bug, or error labels May 6, 2019

gpshead assigned gpshead and unassigned ewdurbin May 6, 2019

gpshead assigned ewdurbin and unassigned gpshead May 8, 2019

ewdurbin assigned gpshead and unassigned ewdurbin May 8, 2019

gpshead closed this as completed Sep 9, 2019

ezio-melotti transferred this issue from another repository Apr 10, 2022

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self-signed.pythontest.net TLS certificate key is too weak #80997

self-signed.pythontest.net TLS certificate key is too weak #80997

gpshead commented May 6, 2019

gpshead commented May 6, 2019

gpshead commented May 6, 2019

gpshead commented May 8, 2019

ewdurbin commented May 8, 2019

yan12125 mannequin commented May 8, 2019

miss-islington commented May 8, 2019

ned-deily commented May 8, 2019

miss-islington commented May 8, 2019

gpshead commented May 9, 2019

aixtools commented May 21, 2019

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aixtools commented May 21, 2019

yan12125 mannequin commented May 21, 2019

larryhastings commented Jul 13, 2019

gpshead commented Sep 9, 2019

self-signed.pythontest.net TLS certificate key is too weak #80997

self-signed.pythontest.net TLS certificate key is too weak #80997

Comments

gpshead commented May 6, 2019

gpshead commented May 6, 2019

gpshead commented May 6, 2019

gpshead commented May 8, 2019

ewdurbin commented May 8, 2019

yan12125 mannequin commented May 8, 2019

miss-islington commented May 8, 2019

ned-deily commented May 8, 2019

miss-islington commented May 8, 2019

gpshead commented May 9, 2019

aixtools commented May 21, 2019

aixtools commented May 21, 2019

aixtools commented May 21, 2019

yan12125 mannequin commented May 21, 2019

larryhastings commented Jul 13, 2019

gpshead commented Sep 9, 2019