Unfortunately that effort is moot, it's really not possible to make python2.7 compatible with OpenSSL 3.0.0, I mean even the latest Python versions are not 100% compatible for various reasons.

In trying to make it compatible there are also ABI changes introduced, it's not only about having the tests pass. The ssl module is already complex enough in backporting changes from the master Python branch to previous 3.x versions, doing that for 2.7 without a full fledged effort from SSL and the Python C API experts guarantee there's gonna be regressions. And that's not even taking into account the security implications of randomly cherry-picking commits just to have the package compile.

On Wed, Jun 29, 2022 at 5:12 PM Dmitry Belyavskiy <dbelyavs@redhat.com> wrote:
Dear colleagues,

If I correctly follow the discussion, the biggest show-stopper is Python 2.*, which has some incomplete patches to deal with OpenSSL 3.0.
If we assist you in moving these patches forward, can we get rid of the devel package and leave the compat package only for 3rd-party packages?

I don't think that the community really requires support for this package for 7 years after its upstream sunset.

Many thanks!

On Tue, Jun 28, 2022 at 4:06 PM Miro Hrončok <mhroncok@redhat.com> wrote:
On 27. 06. 22 13:27, Richard W.M. Jones wrote:
> ======================================================================
> FAIL: test_openssl_version (test.test_ssl.BasicSocketTests)
> ----------------------------------------------------------------------
> Traceback (most recent call last):
>    File "/home/rjones/d/cpython-2.7/Lib/test/test_ssl.py", line 382, in test_openssl_version
>      (s, t))
> AssertionError: ('OpenSSL 3.0.3 3 May 2022', (3, 0, 0, 3, 0))

Might be https://github.com/python/cpython/issues/90272

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