Windows Server Install: ssl.SSLCertVerificationError: [SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed: unable to get local issuer certificate

Related #76 (now closed)

Windows Server 2022 Standard.

PS C:\Users\Administrator> py --version
Python 3.10.11

PS C:\Users\Administrator> pip --version
pip 23.1.2 from C:\Python310\lib\site-packages\pip (python 3.10)

PS C:\Users\Administrator> (Invoke-WebRequest -Uri https://install.python-poetry.org -UseBasicParsing).Content | py -
Retrieving Poetry metadata
Traceback (most recent call last):
  File "C:\Python310\lib\urllib\request.py", line 1348, in do_open
    h.request(req.get_method(), req.selector, req.data, headers,
  File "C:\Python310\lib\http\client.py", line 1283, in request
    self._send_request(method, url, body, headers, encode_chunked)
  File "C:\Python310\lib\http\client.py", line 1329, in _send_request
    self.endheaders(body, encode_chunked=encode_chunked)
  File "C:\Python310\lib\http\client.py", line 1278, in endheaders
    self._send_output(message_body, encode_chunked=encode_chunked)
  File "C:\Python310\lib\http\client.py", line 1038, in _send_output
    self.send(msg)
  File "C:\Python310\lib\http\client.py", line 976, in send
    self.connect()
  File "C:\Python310\lib\http\client.py", line 1455, in connect
    self.sock = self._context.wrap_socket(self.sock,
  File "C:\Python310\lib\ssl.py", line 513, in wrap_socket
    return self.sslsocket_class._create(
  File "C:\Python310\lib\ssl.py", line 1071, in _create
    self.do_handshake()
  File "C:\Python310\lib\ssl.py", line 1342, in do_handshake
    self._sslobj.do_handshake()
ssl.SSLCertVerificationError: [SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed: unable to get local issuer certificate (_ssl.c:1007)

During handling of the above exception, another exception occurred:

Traceback (most recent call last):
  File "<stdin>", line 940, in <module>
  File "<stdin>", line 919, in main
  File "<stdin>", line 516, in run
  File "<stdin>", line 775, in get_version
  File "<stdin>", line 836, in _get
  File "C:\Python310\lib\urllib\request.py", line 216, in urlopen
    return opener.open(url, data, timeout)
  File "C:\Python310\lib\urllib\request.py", line 519, in open
    response = self._open(req, data)
  File "C:\Python310\lib\urllib\request.py", line 536, in _open
    result = self._call_chain(self.handle_open, protocol, protocol +
  File "C:\Python310\lib\urllib\request.py", line 496, in _call_chain
    result = func(*args)
  File "C:\Python310\lib\urllib\request.py", line 1391, in https_open
    return self.do_open(http.client.HTTPSConnection, req,
  File "C:\Python310\lib\urllib\request.py", line 1351, in do_open
    raise URLError(err)
urllib.error.URLError: <urlopen error [SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed: unable to get local issuer certificate (_ssl.c:1007)>

However, unlike #76, installing certifi package does not solve the problem anymore.

PS C:\Users\Administrator> pip install --upgrade certifi
Collecting certifi
  Using cached certifi-2022.12.7-py3-none-any.whl (155 kB)
Installing collected packages: certifi
Successfully installed certifi-2022.12.7
PS C:\Users\Administrator>

PS C:\Users\Administrator> (Invoke-WebRequest -Uri https://install.python-poetry.org -UseBasicParsing).Content | py -
Retrieving Poetry metadata
Traceback (most recent call last):
  File "C:\Python310\lib\urllib\request.py", line 1348, in do_open
    h.request(req.get_method(), req.selector, req.data, headers,
  File "C:\Python310\lib\http\client.py", line 1283, in request
    self._send_request(method, url, body, headers, encode_chunked)
  File "C:\Python310\lib\http\client.py", line 1329, in _send_request
    self.endheaders(body, encode_chunked=encode_chunked)
  File "C:\Python310\lib\http\client.py", line 1278, in endheaders
    self._send_output(message_body, encode_chunked=encode_chunked)
  File "C:\Python310\lib\http\client.py", line 1038, in _send_output
    self.send(msg)
  File "C:\Python310\lib\http\client.py", line 976, in send
    self.connect()
  File "C:\Python310\lib\http\client.py", line 1455, in connect
    self.sock = self._context.wrap_socket(self.sock,
  File "C:\Python310\lib\ssl.py", line 513, in wrap_socket
    return self.sslsocket_class._create(
  File "C:\Python310\lib\ssl.py", line 1071, in _create
    self.do_handshake()
  File "C:\Python310\lib\ssl.py", line 1342, in do_handshake
    self._sslobj.do_handshake()
ssl.SSLCertVerificationError: [SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed: unable to get local issuer certificate (_ssl.c:1007)

During handling of the above exception, another exception occurred:

Traceback (most recent call last):
  File "<stdin>", line 940, in <module>
  File "<stdin>", line 919, in main
  File "<stdin>", line 516, in run
  File "<stdin>", line 775, in get_version
  File "<stdin>", line 836, in _get
  File "C:\Python310\lib\urllib\request.py", line 216, in urlopen
    return opener.open(url, data, timeout)
  File "C:\Python310\lib\urllib\request.py", line 519, in open
    response = self._open(req, data)
  File "C:\Python310\lib\urllib\request.py", line 536, in _open
    result = self._call_chain(self.handle_open, protocol, protocol +
  File "C:\Python310\lib\urllib\request.py", line 496, in _call_chain
    result = func(*args)
  File "C:\Python310\lib\urllib\request.py", line 1391, in https_open
    return self.do_open(http.client.HTTPSConnection, req,
  File "C:\Python310\lib\urllib\request.py", line 1351, in do_open
    raise URLError(err)
urllib.error.URLError: <urlopen error [SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed: unable to get local issuer certificate (_ssl.c:1007)>

まず、Windows Server 2022 上の Python 3.10.11 で install.python-poetry.org の失敗を再現し、その後、トレースバックに示されている urllib と ssl の呼び出しを調べます。この環境で certifi がインストールされている場合も含め、Poetry インストーラーがメタデータを正常に取得できれば完了です。