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

[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.

-- 
You received this bug notification because you are a member of Ubuntu
Foundations Bugs, which is subscribed to openssl in Ubuntu.
https://bugs.launchpad.net/bugs/1899878

Title:
  Python's test_ssl fails starting from Ubuntu 20.04

Status in openssl package in Ubuntu:
  Incomplete

Bug description:
  Please take a look at https://bugs.python.org/issue41561. Developers
  who work on Python think that the issue is due to a change in Ubuntu
  20.04 that is best described by
  https://bugs.python.org/issue41561#msg378089:

  "It sounds like a Debian/Ubuntu patch is breaking an assumption. Did
  somebody report the bug with Debian/Ubuntu maintainers of OpenSSL
  already? Fedora also configures OpenSSL with minimum protocol version
  of TLS 1.2. The distribution does it in a slightly different way that
  makes the restriction discoverable and that is compatible with
  Python's test suite."

To manage notifications about this bug go to:
https://bugs.launchpad.net/ubuntu/+source/openssl/+bug/1899878/+subscriptions