Giampaolo Rodola' <g.rod...@gmail.com> added the comment:

Fortunately errno was set.
Patch in attachment introduces the following changes:

=== 1 ===

Before:
>>> ssl.wrap_socket(socket.socket(), server_side=1)
>>>

Now:
>>> ssl.wrap_socket(socket.socket(), server_side=1)
ValueError: certfile must be specified for server-side operations


=== 2 ===

Before:
>>> s = ssl.wrap_socket(socket.socket(), server_side=1, 
>>> certfile='Lib/test/keycert.pem')
>>> s.connect(('blogger.com', 443))
>>>

Now:
>>> s = ssl.wrap_socket(socket.socket(), server_side=1, 
>>> certfile='Lib/test/keycert.pem')
>>> s.connect(('blogger.com', 443))
ValueError: can't connect in server-side mode


=== 3 ===

Before:
>>> os.path.exists('xxx')
False
>>> ssl.wrap_socket(socket.socket(), certfile='xxx')
ssl.SSLError: [Errno 336445442] _ssl.c:1604: error:140DC002:SSL 
routines:SSL_CTX_use_certificate_chain_file:system lib

Now:
>>> os.path.exists('xxx')
False
>>> ssl.wrap_socket(socket.socket(), certfile='xxx')
IOError: [Errno 2] No such file or directory


=== 4 ===

Before:
>>> os.path.exists('xxx')
False
>>> ctx = ssl.SSLContext(ssl.PROTOCOL_TLSv1)
>>> ctx.load_verify_locations('xxx')
ssl.SSLError: [Errno 185090050] _ssl.c:1676: error:0B084002:x509 certificate 
routines:X509_load_cert_crl_file:system lib

Now:
>>> os.path.exists('xxx')
False
>>> ctx = ssl.SSLContext(ssl.PROTOCOL_TLSv1)
>>> ctx.load_verify_locations('xxx')
IOError: [Errno 2] No such file or directory

----------
keywords: +patch
Added file: http://bugs.python.org/file18673/ssl-errors.patch

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<http://bugs.python.org/issue9706>
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