I don't think using SSL works with hotmail. I tried using:
smtplib.*SMTP_SSL*("smtp.live.com", 587)
smtplib.login(user, passwd)
...
That gave this error:
Traceback (most recent call last):
File "sendemail.py", line 22, in <module>
smtp = smtplib.SMTP_SSL(smtp_srv, 587)
File "/usr/lib/python2.7/smtplib.py", line 776, in __init__
SMTP.__init__(self, host, port, local_hostname, timeout)
File "/usr/lib/python2.7/smtplib.py", line 249, in __init__
(code, msg) = self.connect(host, port)
File "/usr/lib/python2.7/smtplib.py", line 309, in connect
self.sock = self._get_socket(host, port, self.timeout)
File "/usr/lib/python2.7/smtplib.py", line 782, in _get_socket
new_socket = ssl.wrap_socket(new_socket, self.keyfile, self.certfile)
File "/usr/lib/python2.7/ssl.py", line 381, in wrap_socket
ciphers=ciphers)
File "/usr/lib/python2.7/ssl.py", line 143, in __init__
self.do_handshake()
File "/usr/lib/python2.7/ssl.py", line 305, in do_handshake
self._sslobj.do_handshake()
ssl.SSLError: [Errno 1] _ssl.c:504: error:140770FC:SSL
routines:SSL23_GET_SERVER_HELLO:unknown protocol
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