Ronald Oussoren added the comment:

The one difference between the system openssl and a separately compiled one is 
that the former can use the CA root from the KeyChain (and uses a private API 
to do that, as noted earlier).

I just stumbled across a utility that can sync the KeyChain to an OpenSSL CA 
file: 
<https://svn.macports.org/repository/macports/trunk/dports/security/certsync/files/certsync.m>,
 and a blog message at 
<http://landonf.bikemonkey.org/code/macosx/certsync.20130514.html>

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Python tracker <rep...@bugs.python.org>
<http://bugs.python.org/issue17128>
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