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Yep, I am sure Ronald, the RH server has no special configuration. 
The RH box actually immediately connects to the server, an because it requires a certificate returns a 403 forbidden code:
[opentrails@redhat5 ~]$ uname -a
Linux redhat5.ultralat.com 2.6.18-8.el5 #1 SMP Fri Jan 26 14:15:14 EST 2007 x86_64 x86_64 x86_64 GNU/Linux
[opentrails@redhat5 ~]$ python
Python 2.6.5 (r265:79063, Dec 1 2010, 19:40:01) 
[GCC 4.1.1 20070105 (Red Hat 4.1.1-52)] on linux2
Type "help", "copyright", "credits" or "license" for more information.
>>> import urllib2
>>> response = urllib2.urlopen('https://www.finratrace.org/')
Traceback (most recent call last):
 File "<stdin>", line 1, in <module>
 File "/usr/local/lib/python2.6/urllib2.py", line 126, in urlopen
 return _opener.open(url, data, timeout)
 File "/usr/local/lib/python2.6/urllib2.py", line 397, in open
 response = meth(req, response)
 File "/usr/local/lib/python2.6/urllib2.py", line 510, in http_response
 'http', request, response, code, msg, hdrs)
 File "/usr/local/lib/python2.6/urllib2.py", line 435, in error
 return self._call_chain(*args)
 File "/usr/local/lib/python2.6/urllib2.py", line 369, in _call_chain
 result = func(*args)
 File "/usr/local/lib/python2.6/urllib2.py", line 518, in http_error_default
 raise HTTPError(req.get_full_url(), code, msg, hdrs, fp)
urllib2.HTTPError: HTTP Error 403: Forbidden
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And "HTTP Error 403: Forbidden: is what MAC OS X should return as well when the certificate was not sent.
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Furthermore, MAC OS X hangs even with the second sample code, which provides the certificate and the authentication, failing as well.
See the section "====>Same thing happens Using python 2.7.1" on my original post. That example sends the certificate and the authentication but it simply hangs, getting the "httplib.BadStatusLine: ''" error at the end.
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Now, if I send the authentication and certificate under the linux box, it works fine:
[opentrails@redhat5 ~]$ uname -a
Linux redhat5.ultralat.com 2.6.18-8.el5 #1 SMP Fri Jan 26 14:15:14 EST 2007 x86_64 x86_64 x86_64 GNU/Linux
[opentrails@redhat5 ~]$ python
Python 2.6.5 (r265:79063, Dec 1 2010, 19:40:01) 
[GCC 4.1.1 20070105 (Red Hat 4.1.1-52)] on linux2
Type "help", "copyright", "credits" or "license" for more information.
>>> import httplib,base64
>>> 
>>> key,cert=('/tmp/cert_nopwd.pem',)*2
>>> HOSTNAME = 'www.finratrace.org'
>>> 
>>> username,password='mysuer','mypass'
>>> 
>>> base64string = base64.encodestring('%s:%s' % (username, password))[:-1]
>>> 
>>> 
>>> conn = httplib.HTTPSConnection(HOSTNAME,key_file = key,cert_file = cert)
>>> conn.putrequest('GET', '/')
>>> conn.putheader("Authorization", "Basic %s" % base64string)
>>> 
>>> conn.endheaders()
>>> response = conn.getresponse()
>>> print response.status,response.reason
200 OK
>>> html= response.read()
>>> open("/tmp/kk.html",'w').write(html)
>>> 
I attached the response file from the web site.
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By the way, I am using openssl 0.9.8 in both machines:
imac:bin isaac$ uname -a 
Darwin imac.localdomain 10.7.0 Darwin Kernel Version 10.7.0: Sat Jan 29 15:16:10 PST 2011; root:xnu-1504937~1/RELEASE_X86_64 x86_64
imac:bin isaac$ openssl version
OpenSSL 0.9.8l 5 Nov 2009
- - - - - - - - - - - - - -
Redhat has two openssl flavors:
[opentrails@redhat5 ~]$ openssl version
OpenSSL 0.9.8b 04 May 2006
[opentrails@redhat5 ~]$ /usr/local/ssl/bin/openssl version
OpenSSL 0.9.8p 16 Nov 2010
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In case it might help, this was working with MAC OS X 10.4 with PPC. It started to fail when I upgraded to an intel iMac with OSX 10.6. I do not know if it has something to do with the 64 bits kernel.