OpenSSL errors in python requests

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Running python version 3.9.1 on arch linux with OpenSSL version 1.1.1i and pyopenssl version 1.1.1i I get the following error when trying to use an https proxy with the requests module:

    Traceback (most recent call last):
  File "/usr/lib/python3.9/site-packages/urllib3/connectionpool.py", line 696, in urlopen
    self._prepare_proxy(conn)
  File "/usr/lib/python3.9/site-packages/urllib3/connectionpool.py", line 964, in _prepare_proxy
    conn.connect()
  File "/usr/lib/python3.9/site-packages/urllib3/connection.py", line 359, in connect
    conn = self._connect_tls_proxy(hostname, conn)
  File "/usr/lib/python3.9/site-packages/urllib3/connection.py", line 496, in _connect_tls_proxy
    return ssl_wrap_socket(
  File "/usr/lib/python3.9/site-packages/urllib3/util/ssl_.py", line 424, in ssl_wrap_socket
    ssl_sock = _ssl_wrap_socket_impl(sock, context, tls_in_tls)
  File "/usr/lib/python3.9/site-packages/urllib3/util/ssl_.py", line 466, in _ssl_wrap_socket_impl
    return ssl_context.wrap_socket(sock)
  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()
ssl.SSLError: [SSL: WRONG_VERSION_NUMBER] wrong version number (_ssl.c:1123)

During handling of the above exception, another exception occurred:

Traceback (most recent call last):
  File "/usr/lib/python3.9/site-packages/requests/adapters.py", line 439, in send
    resp = conn.urlopen(
  File "/usr/lib/python3.9/site-packages/urllib3/connectionpool.py", line 755, in urlopen
    retries = retries.increment(
  File "/usr/lib/python3.9/site-packages/urllib3/util/retry.py", line 573, in increment
    raise MaxRetryError(_pool, url, error or ResponseError(cause))
urllib3.exceptions.MaxRetryError: HTTPSConnectionPool(host='google.com', port=443): Max retries exceeded with url: / (Caused by SSLError(SSLError(1, '[SSL: WRONG_VERSION_NUMBER] wrong version number (_ssl.c:1123)')))

During handling of the above exception, another exception occurred:

Traceback (most recent call last):
  File "<stdin>", line 1, in <module>
  File "/usr/lib/python3.9/site-packages/requests/api.py", line 76, in get
    return request('get', url, params=params, **kwargs)
  File "/usr/lib/python3.9/site-packages/requests/api.py", line 61, in request
    return session.request(method=method, url=url, **kwargs)
  File "/usr/lib/python3.9/site-packages/requests/sessions.py", line 542, in request
    resp = self.send(prep, **send_kwargs)
  File "/usr/lib/python3.9/site-packages/requests/sessions.py", line 655, in send
    r = adapter.send(request, **kwargs)
  File "/usr/lib/python3.9/site-packages/requests/adapters.py", line 514, in send
    raise SSLError(e, request=request)
requests.exceptions.SSLError: HTTPSConnectionPool(host='google.com', port=443): Max retries exceeded with url: / (Caused by SSLError(SSLError(1, '[SSL: WRONG_VERSION_NUMBER] wrong version number (_ssl.c:1123)')))

The code I am running is:

import requests

proxy = {
    'https' : 'https://proxyip:proxyport'
}

requests.get("https://google.com", proxies=proxy)

No matter what https proxy I try, I get the same error. I have also reinstalled both openssl and python with no change. Any suggestions?

python-requests openssl python-3.x ssl python
3 Answers
... line 496, in _connect_tls_proxy

Your code is trying to use the (new) support for accessing the proxy itself over HTTPS. This is done because you've explicitly given that URL as the proxy as https://... and not http://...:

'https' : 'https://proxyip:proxyport'
           ^^^^^^

It is very likely that the proxy itself does not support TLS connections to the proxy. Commonly HTTP proxies have a plain HTTP connections to the proxy only. They still can proxy HTTPS traffic this way, since the client will simply issue a CONNECT request to the proxy to create a tunnel and then use end-to-end TLS between client and server.

Accessing a proxy by HTTPS will add an additional layer of TLS between client and proxy, which is not supported by most proxies. Therefore, you likely need plain HTTP proxy instead:

 'https' : 'http://proxyip:proxyport'
           ^^^^^^

Note that in older versions of the requests library both access with http:// and https:// worked. These older versions had no support for HTTPS to the proxy and simply used plain HTTP even if https:// would be specified.

user_30810180

enter image description here

Add login.microsoftonline.com;management.azure.com as exceptions will work.

user_99220660

it was fixed with my case by this command:

 python3 -m pip install urllib3==1.22
user_97910390
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