deploy-freenas fails with certificate errors

I used this script for some while for updating FreeNAS' certificate and it worked fine. For some reason I could not identify yet, it stopped working. I tried rebuilding the jail and reconfiguring everything I can think of, but it keeps failing with SSL error-messages. I use FreeNAS-11.3-U3.1. I searched for the error-message with "max retries exceeded" and found some advice that it could be connected to broken DNS, but DNS is working fine in the jail and the host.

root@webserver:/usr/local/share/deploy-freenas # ./deploy_freenas.py
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', 'SSL23_GET_SERVER_HELLO', 'tlsv1 alert internal error')]

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', 'SSL23_GET_SERVER_HELLO', 'tlsv1 alert internal error')])",)

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='<FQDN>', port=443): Max retries exceeded with url: /api/v1.0/system/certificate/import/ (Caused by SSLError(SSLError("bad handshake: Error([('SSL routines', 'SSL23_GET_SERVER_HELLO', 'tlsv1 alert internal error')])")))

During handling of the above exception, another exception occurred:

Traceback (most recent call last):
  File "./deploy_freenas.py", line 73, in <module>
    "cert_privatekey": priv_key,
  File "/usr/local/lib/python3.7/site-packages/requests/api.py", line 116, in post
    return request('post', url, data=data, json=json, **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/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='<FQDN>', port=443): Max retries exceeded with url: /api/v1.0/system/certificate/import/ (Caused by SSLError(SSLError("bad handshake: Error([('SSL routines', 'SSL23_GET_SERVER_HELLO', 'tlsv1 alert internal error')])")))

danb35 / deploy-freenas

deploy-freenas fails with certificate errors #21