The docstring for Context.check_privatekey() correctly
says:
Returns: None (raises an exception if something's wrong)
However, the documentation at
http://pyopenssl.sourceforge.net/pyOpenSSL.html/openssl-context.html
says:
Returns true if they match, false otherwise.
The HTML doc (or, rather, the pyOpenSSL.tex file)
should be fixed.
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I've applied a patch to the documentation to my fork of pyOpenSSL at http://launchpad.net/pyopenssl which fixes the tex file. The changeset is revision 31.
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I've also updated the sourceforge website, now.