This looks like a recurrence of: https://bugs.freebsd.org/bugzilla/show_bug.cgi?id=262730

[testuser@freebsd /home/testuser] deluged
Traceback (most recent call last):
  File "/usr/local/lib/python3.9/site-packages/pkg_resources/__init__.py", line 581, in _build_master
    ws.require(__requires__)
  File "/usr/local/lib/python3.9/site-packages/pkg_resources/__init__.py", line 909, in require
    needed = self.resolve(parse_requirements(requirements))
  File "/usr/local/lib/python3.9/site-packages/pkg_resources/__init__.py", line 800, in resolve
    raise VersionConflict(dist, req).with_context(dependent_req)
pkg_resources.ContextualVersionConflict: (cryptography 42.0.5 (/usr/local/lib/python3.9/site-packages), Requirement.parse('cryptography!=40.0.0,!=40.0.1,<42,>=38.0.0'), {'pyopenssl'})

During handling of the above exception, another exception occurred:

Traceback (most recent call last):
  File "/usr/local/bin/deluged", line 33, in <module>
    sys.exit(load_entry_point('deluge==2.1.1', 'gui_scripts', 'deluged')())
  File "/usr/local/bin/deluged", line 25, in importlib_load_entry_point
    return next(matches).load()
  File "/usr/local/lib/python3.9/importlib/metadata.py", line 86, in load
    module = import_module(match.group('module'))
  File "/usr/local/lib/python3.9/importlib/__init__.py", line 127, in import_module
    return _bootstrap._gcd_import(name[level:], package, level)
  File "<frozen importlib._bootstrap>", line 1030, in _gcd_import
  File "<frozen importlib._bootstrap>", line 1007, in _find_and_load
  File "<frozen importlib._bootstrap>", line 986, in _find_and_load_unlocked
  File "<frozen importlib._bootstrap>", line 680, in _load_unlocked
  File "<frozen importlib._bootstrap_external>", line 850, in exec_module
  File "<frozen importlib._bootstrap>", line 228, in _call_with_frames_removed
  File "/usr/local/lib/python3.9/site-packages/deluge/core/daemon_entry.py", line 15, in <module>
    from deluge.argparserbase import ArgParserBase
  File "/usr/local/lib/python3.9/site-packages/deluge/argparserbase.py", line 16, in <module>
    import deluge.log
  File "/usr/local/lib/python3.9/site-packages/deluge/log.py", line 22, in <module>
    from deluge import common
  File "/usr/local/lib/python3.9/site-packages/deluge/common.py", line 30, in <module>
    import pkg_resources
  File "/usr/local/lib/python3.9/site-packages/pkg_resources/__init__.py", line 3260, in <module>
    def _initialize_master_working_set():
  File "/usr/local/lib/python3.9/site-packages/pkg_resources/__init__.py", line 3234, in _call_aside
    f(*args, **kwargs)
  File "/usr/local/lib/python3.9/site-packages/pkg_resources/__init__.py", line 3272, in _initialize_master_working_set
    working_set = WorkingSet._build_master()
  File "/usr/local/lib/python3.9/site-packages/pkg_resources/__init__.py", line 583, in _build_master
    return cls._build_from_requirements(__requires__)
  File "/usr/local/lib/python3.9/site-packages/pkg_resources/__init__.py", line 596, in _build_from_requirements
    dists = ws.resolve(reqs, Environment())
  File "/usr/local/lib/python3.9/site-packages/pkg_resources/__init__.py", line 795, in resolve
    raise DistributionNotFound(req, requirers)
pkg_resources.DistributionNotFound: The 'cryptography!=40.0.0,!=40.0.1,<42,>=38.0.0' distribution was not found and is required by pyopenssl