Adding a new Jail in FreeNAS:

The error:

HTTPSConnectionPool(host='www.freebsd.org', port=443): Max retries exceeded with url: /security/unsupported.html (Caused by SSLError(SSLError("bad handshake: Error([('SSL routines', 'ssl3_get_server_certificate', 'certificate verify failed')])")))

Error: Traceback (most recent call last):
  File "/usr/local/lib/python3.7/site-packages/urllib3/contrib/pyopenssl.py", line 485, in wrap_socket
    cnx.do_handshake()
  File "/usr/local/lib/python3.7/site-packages/OpenSSL/SSL.py", line 1915, in do_handshake
    self._raise_ssl_error(self._ssl, result)
  File "/usr/local/lib/python3.7/site-packages/OpenSSL/SSL.py", line 1647, in _raise_ssl_error
    _raise_current_error()
  File "/usr/local/lib/python3.7/site-packages/OpenSSL/_util.py", line 54, in exception_from_error_queue
    raise exception_type(errors)
OpenSSL.SSL.Error: [('SSL routines', 'ssl3_get_server_certificate', 'certificate verify failed')]

During handling of the above exception, another exception occurred:

Traceback (most recent call last):
  File "/usr/local/lib/python3.7/site-packages/urllib3/connectionpool.py", line 672, in urlopen
    chunked=chunked,
  File "/usr/local/lib/python3.7/site-packages/urllib3/connectionpool.py", line 376, in _make_request
    self._validate_conn(conn)
  File "/usr/local/lib/python3.7/site-packages/urllib3/connectionpool.py", line 994, in _validate_conn
    conn.connect()
  File "/usr/local/lib/python3.7/site-packages/urllib3/connection.py", line 394, in connect
    ssl_context=context,
  File "/usr/local/lib/python3.7/site-packages/urllib3/util/ssl_.py", line 370, in ssl_wrap_socket
    return context.wrap_socket(sock, server_hostname=server_hostname)
  File "/usr/local/lib/python3.7/site-packages/urllib3/contrib/pyopenssl.py", line 491, in wrap_socket
    raise ssl.SSLError("bad handshake: %r" % e)
ssl.SSLError: ("bad handshake: Error([('SSL routines', 'ssl3_get_server_certificate', 'certificate verify failed')])",)

During handling of the above exception, another exception occurred:

Traceback (most recent call last):
  File "/usr/local/lib/python3.7/site-packages/requests/adapters.py", line 449, in send
    timeout=timeout
  File "/usr/local/lib/python3.7/site-packages/urllib3/connectionpool.py", line 720, in urlopen
    method, url, error=e, _pool=self, _stacktrace=sys.exc_info()[2]
  File "/usr/local/lib/python3.7/site-packages/urllib3/util/retry.py", line 436, in increment
    raise MaxRetryError(_pool, url, error or ResponseError(cause))
urllib3.exceptions.MaxRetryError: HTTPSConnectionPool(host='www.freebsd.org', port=443): Max retries exceeded with url: /security/unsupported.html (Caused by SSLError(SSLError("bad handshake: Error([('SSL routines', 'ssl3_get_server_certificate', 'certificate verify failed')])")))

During handling of the above exception, another exception occurred:

Traceback (most recent call last):
  File "/usr/local/lib/python3.7/site-packages/middlewared/main.py", line 130, in call_method
    io_thread=False)
  File "/usr/local/lib/python3.7/site-packages/middlewared/main.py", line 1091, in _call
    return await run_method(methodobj, *args)
  File "/usr/local/lib/python3.7/site-packages/middlewared/main.py", line 1015, in _run_in_conn_threadpool
    return await self.run_in_executor(self.__ws_threadpool, method, *args, **kwargs)
  File "/usr/local/lib/python3.7/site-packages/middlewared/main.py", line 1003, in run_in_executor
    return await loop.run_in_executor(pool, functools.partial(method, *args, **kwargs))
  File "/usr/local/lib/python3.7/concurrent/futures/thread.py", line 57, in run
    result = self.fn(*self.args, **self.kwargs)
  File "/usr/local/lib/python3.7/site-packages/middlewared/schema.py", line 965, in nf
    return f(*args, **kwargs)
  File "/usr/local/lib/python3.7/site-packages/middlewared/plugins/jail.py", line 658, in releases_choices
    choices = {str(k): str(k) for k in ListableReleases(remote=remote)}
  File "/usr/local/lib/python3.7/site-packages/iocage_lib/release.py", line 46, in __init__
    self.eol_list = IOCFetch.__fetch_eol_check__()
  File "/usr/local/lib/python3.7/site-packages/iocage_lib/ioc_fetch.py", line 114, in __fetch_eol_check__
    req = requests.get(_eol)
  File "/usr/local/lib/python3.7/site-packages/requests/api.py", line 75, in get
    return request('get', url, params=params, **kwargs)
  File "/usr/local/lib/python3.7/site-packages/requests/api.py", line 60, in request
    return session.request(method=method, url=url, **kwargs)
  File "/usr/local/lib/python3.7/site-packages/requests/sessions.py", line 533, in request
    resp = self.send(prep, **send_kwargs)
  File "/usr/local/lib/python3.7/site-packages/raven/breadcrumbs.py", line 341, in send
    resp = real_send(self, request, *args, **kwargs)
  File "/usr/local/lib/python3.7/site-packages/requests/sessions.py", line 646, in send
    r = adapter.send(request, **kwargs)
  File "/usr/local/lib/python3.7/site-packages/requests/adapters.py", line 514, in send
    raise SSLError(e, request=request)
requests.exceptions.SSLError: HTTPSConnectionPool(host='www.freebsd.org', port=443): Max retries exceeded with url: /security/unsupported.html (Caused by SSLError(SSLError("bad handshake: Error([('SSL routines', 'ssl3_get_server_certificate', 'certificate verify failed')])")))

Someone suggested this fix:

 mv /usr/local/lib/python3.7/site-packages/certifi/cacert.pem /usr/local/lib/python3.7/site-packages/certifi/cacert.pem.old

ln -s /usr/local/share/certs/ca-root-nss.crt /usr/local/lib/python3.7/site-packages/certifi/cacert.pem

But if it doesn’t work for you, then you just need to upgrade to version 12 instead:

Go to System -> Update:

Add a new jail should work now: