SOLVED Unable to connect to Update Server

[Khilbron]

When trying to create a new jail for a manual PLEX install (because the plugin broke, but that's another thing entirely.) the Jail creation wizard threw the following error:

Code:

Error: Traceback (most recent call last):
  File "/usr/local/lib/python3.8/site-packages/urllib3/connection.py", line 156, in _new_conn
    conn = connection.create_connection(
  File "/usr/local/lib/python3.8/site-packages/urllib3/util/connection.py", line 61, in create_connection
    for res in socket.getaddrinfo(host, port, family, socket.SOCK_STREAM):
  File "/usr/local/lib/python3.8/socket.py", line 918, in getaddrinfo
    for res in _socket.getaddrinfo(host, port, family, type, proto, flags):
socket.gaierror: [Errno 8] Name does not resolve

During handling of the above exception, another exception occurred:

Traceback (most recent call last):
  File "/usr/local/lib/python3.8/site-packages/urllib3/connectionpool.py", line 665, in urlopen
    httplib_response = self._make_request(
  File "/usr/local/lib/python3.8/site-packages/urllib3/connectionpool.py", line 376, in _make_request
    self._validate_conn(conn)
  File "/usr/local/lib/python3.8/site-packages/urllib3/connectionpool.py", line 994, in _validate_conn
    conn.connect()
  File "/usr/local/lib/python3.8/site-packages/urllib3/connection.py", line 334, in connect
    conn = self._new_conn()
  File "/usr/local/lib/python3.8/site-packages/urllib3/connection.py", line 168, in _new_conn
    raise NewConnectionError(
urllib3.exceptions.NewConnectionError: <urllib3.connection.VerifiedHTTPSConnection object at 0x8203ee8b0>: Failed to establish a new connection: [Errno 8] Name does not resolve

During handling of the above exception, another exception occurred:

Traceback (most recent call last):
  File "/usr/local/lib/python3.8/site-packages/requests/adapters.py", line 439, in send
    resp = conn.urlopen(
  File "/usr/local/lib/python3.8/site-packages/urllib3/connectionpool.py", line 719, in urlopen
    retries = retries.increment(
  File "/usr/local/lib/python3.8/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 NewConnectionError('<urllib3.connection.VerifiedHTTPSConnection object at 0x8203ee8b0>: Failed to establish a new connection: [Errno 8] Name does not resolve'))

During handling of the above exception, another exception occurred:

Traceback (most recent call last):
  File "/usr/local/lib/python3.8/site-packages/middlewared/main.py", line 137, in call_method
    result = await self.middleware._call(message['method'], serviceobj, methodobj, params, app=self,
  File "/usr/local/lib/python3.8/site-packages/middlewared/main.py", line 1206, in _call
    return await self.run_in_executor(prepared_call.executor, methodobj, *prepared_call.args)
  File "/usr/local/lib/python3.8/site-packages/middlewared/main.py", line 1110, in run_in_executor
    return await loop.run_in_executor(pool, functools.partial(method, *args, **kwargs))
  File "/usr/local/lib/python3.8/concurrent/futures/thread.py", line 57, in run
    result = self.fn(*self.args, **self.kwargs)
  File "/usr/local/lib/python3.8/site-packages/middlewared/schema.py", line 977, in nf
    return f(*args, **kwargs)
  File "/usr/local/lib/python3.8/site-packages/middlewared/plugins/jail_freebsd.py", line 799, in releases_choices
    choices = {str(k): str(k) for k in ListableReleases(remote=remote)}
  File "/usr/local/lib/python3.8/site-packages/iocage_lib/release.py", line 47, in __init__
    self.eol_list = IOCFetch.__fetch_eol_check__()
  File "/usr/local/lib/python3.8/site-packages/iocage_lib/ioc_fetch.py", line 114, in __fetch_eol_check__
    req = requests.get(_eol)
  File "/usr/local/lib/python3.8/site-packages/requests/api.py", line 75, in get
    return request('get', url, params=params, **kwargs)
  File "/usr/local/lib/python3.8/site-packages/requests/api.py", line 60, in request
    return session.request(method=method, url=url, **kwargs)
  File "/usr/local/lib/python3.8/site-packages/requests/sessions.py", line 533, in request
    resp = self.send(prep, **send_kwargs)
  File "/usr/local/lib/python3.8/site-packages/requests/sessions.py", line 646, in send
    r = adapter.send(request, **kwargs)
  File "/usr/local/lib/python3.8/site-packages/requests/adapters.py", line 516, in send
    raise ConnectionError(e, request=request)
requests.exceptions.ConnectionError: HTTPSConnectionPool(host='www.freebsd.org', port=443): Max retries exceeded with url: /security/unsupported.html (Caused by NewConnectionError('<urllib3.connection.VerifiedHTTPSConnection object at 0x8203ee8b0>: Failed to establish a new connection: [Errno 8] Name does not resolve'))

I wasn't sure what that meant, but the wizard was unable to display any releases in the dropdown:

Figured I'd check for updates, and it turns out that my system can't see the update server:

I can't ping the update server (update-master.ixsystems.com) either.
Checking the URL in a browser gives me the correct update train.
Another user had a problem with the date. My system's date is correct.

I was reinstalling PLEX b/c it wasn't able to generate an IP using DHCP. I suspect the source of these issues is more network-related then TrueNAS related, but I am not really sure where to start looking.

 

[Khilbron]

Found the problem: Apparently at some point along the way my default gateway was removed.
For those that encounter the same problem and end up here follow the instructions here: https://www.truenas.com/community/threads/cant-install-transmission-plugin.92057/