The cryptography package 0.9+ __init__ emits a DeprecationWarning
Python 2.6 is no longer supported by the Python core team, please upgrade your Python.
This causes our tests to fail, as they check for 'deprecation' in the output of pwb tests, and some tests assert that there was only 'one deprecation message' after calling one of the deprecated pywikibot functions.
While this message is annoying, the maintainers continue to support Python 2.6, with many test builds, and they have rejected a request to remove those test builds. See https://github.com/pyca/cryptography/issues/2060
T103769 implemented a workaround for Python 2.6 which pinned the cryptography version to 0.8.2. This will mean Python 2.6 users will face unusual problems connecting to some https servers, due to bugs that have been fixed in cryptography v0.9+, and possibly even security bugs.
Another solution needs to be found.