New submission from Darren Skidmore <darrenrs0...@gmail.com>:

As of Python 3.9.1, when attempting to perform any SSL requests when a packet 
sniffer tool (e.g. Telerik Fiddler) is intercepting SSL traffic, the program 
will hang for about a minute and then crash with a WRONG_VERSION_NUMBER error. 
This has been tested to occur with urllib2 and requests modules. Alternatives 
such as verify=False and adding the Fiddler Root Certificate to Python's 
cacert.pem file do not rectify this error.

This traceback was generated when attempting to access https://example.com:443 
while Fiddler 5.0.20204.45441 was open:

Traceback (most recent call last):
  File 
"C:\Users\Darren\AppData\Local\Programs\Python\Python39\lib\site-packages\urllib3\connectionpool.py",
 line 696, in urlopen
    self._prepare_proxy(conn)
  File 
"C:\Users\Darren\AppData\Local\Programs\Python\Python39\lib\site-packages\urllib3\connectionpool.py",
 line 964, in _prepare_proxy
    conn.connect()
  File 
"C:\Users\Darren\AppData\Local\Programs\Python\Python39\lib\site-packages\urllib3\connection.py",
 line 359, in connect
    conn = self._connect_tls_proxy(hostname, conn)
  File 
"C:\Users\Darren\AppData\Local\Programs\Python\Python39\lib\site-packages\urllib3\connection.py",
 line 496, in _connect_tls_proxy
    return ssl_wrap_socket(
  File 
"C:\Users\Darren\AppData\Local\Programs\Python\Python39\lib\site-packages\urllib3\util\ssl_.py",
 line 432, in ssl_wrap_socket
    ssl_sock = _ssl_wrap_socket_impl(sock, context, tls_in_tls)
  File 
"C:\Users\Darren\AppData\Local\Programs\Python\Python39\lib\site-packages\urllib3\util\ssl_.py",
 line 474, in _ssl_wrap_socket_impl
    return ssl_context.wrap_socket(sock)
  File "C:\Users\Darren\AppData\Local\Programs\Python\Python39\lib\ssl.py", 
line 500, in wrap_socket
    return self.sslsocket_class._create(
  File "C:\Users\Darren\AppData\Local\Programs\Python\Python39\lib\ssl.py", 
line 1040, in _create
    self.do_handshake()
  File "C:\Users\Darren\AppData\Local\Programs\Python\Python39\lib\ssl.py", 
line 1309, in do_handshake
    self._sslobj.do_handshake()
ssl.SSLError: [SSL: WRONG_VERSION_NUMBER] wrong version number (_ssl.c:1123)

This exact question has recently been asked on StackOverflow: 
https://stackoverflow.com/questions/65516325/ssl-wrong-version-number-on-python-request

----------
assignee: christian.heimes
components: SSL
messages: 385476
nosy: christian.heimes, darrenrs
priority: normal
severity: normal
status: open
title: All SSL requests fail with WRONG_VERSION_NUMBER when a packet sniffer is 
open
type: crash
versions: Python 3.9

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Python tracker <rep...@bugs.python.org>
<https://bugs.python.org/issue43000>
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