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Note that this is a problem in 2.4 and trunk.
The sample code worked fine earlier today if (and only if) I
left out the .settimeout() call.
Note that buildbot test runs are failing in trunk and 2.4
branch now on non-Windows boxes, because the
s.connect(("gmail.org", 995))
line is timing out (the new test is disabled on Windows, and
that's why the Windows buildbots are still passing). At the
moment, that's timing out on my Windows box too. We clearly
need a more reliable net address to connect to.
On Bug Day IRC, "arekm" last asked that I try this patch on
 Windows:
http://pastebin.com/633224
Unfortunately, I haven't been able to get beyond the
s.connect(("gmail.org", 995)) line since then, so still
don't know whether that helps. Nothing else did ;-)
On Windows, in newPySSLObject(),
"ret = SSL_connect(self->ssl);" returns -1
"err = SSL_get_error(self->ssl, ret);" returns 2
"if (err == SSL_ERROR_WANT_READ)" triggers.
check_socket_and_wait_for_timeout() takes the "else if
(s->sock_timeout == 0.0)" path and and returns
SOCKET_IS_NONBLOCKING.
newPySSLObject() breaks out of its loop then, and does
"PySSL_SetError(self, ret); goto fail;"