Issues with "connection timed out"

[duckredbeard]

I have a Raspberry Pi running a python code that is expected to do a requests.post when a PIR detects motion. It works for several days in a row, then fails. The PIR is seeing the motion, as every time it sees the motion, it posts the error that is shown below. Odd is that it is still connected to the internet, as I can VNC into the Pi. If I stop and restart the script, it functions as it should, even if I just had the error a few seconds prior. You can see in the stuff below that it should be printing motion start and motion end stuff, like the first three lines.

Here is the error that shows up in the shell when it fails (posting it as code so indentations remain intact):

Motion ended Fri 15:51:54
Motion started Fri 16:00:12
Motion ended Fri 16:03:27
Traceback (most recent call last):
  File "/usr/lib/python3/dist-packages/urllib3/connectionpool.py", line 699, in urlopen
    httplib_response = self._make_request(
  File "/usr/lib/python3/dist-packages/urllib3/connectionpool.py", line 382, in _make_request
    self._validate_conn(conn)
  File "/usr/lib/python3/dist-packages/urllib3/connectionpool.py", line 1012, in _validate_conn
    conn.connect()
  File "/usr/lib/python3/dist-packages/urllib3/connection.py", line 411, in connect
    self.sock = ssl_wrap_socket(
  File "/usr/lib/python3/dist-packages/urllib3/util/ssl_.py", line 449, in ssl_wrap_socket
    ssl_sock = _ssl_wrap_socket_impl(
  File "/usr/lib/python3/dist-packages/urllib3/util/ssl_.py", line 493, in _ssl_wrap_socket_impl
    return ssl_context.wrap_socket(sock, server_hostname=server_hostname)
  File "/usr/lib/python3.9/ssl.py", line 500, in wrap_socket
    return self.sslsocket_class._create(
  File "/usr/lib/python3.9/ssl.py", line 1040, in _create
    self.do_handshake()
  File "/usr/lib/python3.9/ssl.py", line 1309, in do_handshake
    self._sslobj.do_handshake()
TimeoutError: [Errno 110] Connection timed out

During handling of the above exception, another exception occurred:

Traceback (most recent call last):
  File "/usr/lib/python3/dist-packages/requests/adapters.py", line 439, in send
    resp = conn.urlopen(
  File "/usr/lib/python3/dist-packages/urllib3/connectionpool.py", line 755, in urlopen
    retries = retries.increment(
  File "/usr/lib/python3/dist-packages/urllib3/util/retry.py", line 532, in increment
    raise six.reraise(type(error), error, _stacktrace)
  File "/usr/lib/python3/dist-packages/six.py", line 718, in reraise
    raise value.with_traceback(tb)
  File "/usr/lib/python3/dist-packages/urllib3/connectionpool.py", line 699, in urlopen
    httplib_response = self._make_request(
  File "/usr/lib/python3/dist-packages/urllib3/connectionpool.py", line 382, in _make_request
    self._validate_conn(conn)
  File "/usr/lib/python3/dist-packages/urllib3/connectionpool.py", line 1012, in _validate_conn
    conn.connect()
  File "/usr/lib/python3/dist-packages/urllib3/connection.py", line 411, in connect
    self.sock = ssl_wrap_socket(
  File "/usr/lib/python3/dist-packages/urllib3/util/ssl_.py", line 449, in ssl_wrap_socket
    ssl_sock = _ssl_wrap_socket_impl(
  File "/usr/lib/python3/dist-packages/urllib3/util/ssl_.py", line 493, in _ssl_wrap_socket_impl
    return ssl_context.wrap_socket(sock, server_hostname=server_hostname)
  File "/usr/lib/python3.9/ssl.py", line 500, in wrap_socket
    return self.sslsocket_class._create(
  File "/usr/lib/python3.9/ssl.py", line 1040, in _create
    self.do_handshake()
  File "/usr/lib/python3.9/ssl.py", line 1309, in do_handshake
    self._sslobj.do_handshake()
urllib3.exceptions.ProtocolError: ('Connection aborted.', TimeoutError(110, 'Connection timed out'))

During handling of the above exception, another exception occurred:

Traceback (most recent call last):
  File "/media/pi/C14B-F725/KegMotionV2.py", line 14, in <module>
    r = requests.post("https://autoremotejoaomgcd.appspot.com/sendmessage?key=SecretCodeStuff&message=wakee")
  File "/usr/lib/python3/dist-packages/requests/api.py", line 119, in post
    return request('post', url, data=data, json=json, **kwargs)
  File "/usr/lib/python3/dist-packages/requests/api.py", line 61, in request
    return session.request(method=method, url=url, **kwargs)
  File "/usr/lib/python3/dist-packages/requests/sessions.py", line 542, in request
    resp = self.send(prep, **send_kwargs)
  File "/usr/lib/python3/dist-packages/requests/sessions.py", line 655, in send
    r = adapter.send(request, **kwargs)
  File "/usr/lib/python3/dist-packages/requests/adapters.py", line 498, in send
    raise ConnectionError(err, request=request)
requests.exceptions.ConnectionError: ('Connection aborted.', TimeoutError(110, 'Connection timed out'))