<html><head><meta http-equiv="Content-Type" content="text/html; charset=utf-8"></head><body style="word-wrap: break-word; -webkit-nbsp-mode: space; line-break: after-white-space;" class="">I haven’t been able to identify the correct incantation that will point pip at a CA chain that avoids this issue, whether caused by an old LetsEncrypt cert or some other old cert.<div class=""><br class=""></div><div class="">For example, this command using --cert along with an up-to-date curl-ca-bundle (that addresses the LetsEncrypt cert issue) fails with the same error:<br class=""><div class=""><br class=""></div><div class=""><blockquote type="cite" class=""><div style="margin: 0px; font-stretch: normal; line-height: normal; font-family: Menlo;" class=""><span style="font-variant-ligatures: no-common-ligatures;" class=""><font size="4" class="">pip-2.7 install --cert /opt/local/etc/openssl/cert.pem -I --user setuptools</font></span></div></blockquote><div class=""><br class=""><div><br class=""><blockquote type="cite" class=""><div class="">On Mar 14, 2022, at 9:18 PM, Jim DeLaHunt <<a href="mailto:list+macports-dev@jdlh.com" class="">list+macports-dev@jdlh.com</a>> wrote:</div><br class="Apple-interchange-newline"><div class=""><div class="">On 2022-03-14 17:09, Steven Smith wrote:<br class=""><blockquote type="cite" class="">I’m trying to update calendar-contacts-server to macOS 12.3. This requires installing a bunch of stuff with python2.7’s pip.<br class="">I’m hitting an SSLError at the command:<br class=""><blockquote type="cite" class="">/opt/local/bin/python2.7 -m pip install -I --user setuptools==18.5<br class=""></blockquote>Is there a way of pointing MacPorts python2.7 pip at a set of up-to-date CAs? [Say e.g. from curl-ca-bundle?]<br class=""></blockquote><br class="">I recall discussion recently on either the macports-dev or the macports-user lists about SSL tools failing due to expiry of Let's Encrypt certificates. I can't locate a link to those threads quickly, and I'm not sure if it applies to your situation.<br class=""><br class="">Have a look at<br class=""><<a href="https://trac.macports.org/wiki/ProblemHotlist#letsencrypt" class="">https://trac.macports.org/wiki/ProblemHotlist#letsencrypt</a>><br class=""><br class="">Is it helpful?<br class=""><br class="">Best regards,<br class=""> --Jim DeLaHunt<br class=""><br class=""><br class=""></div></div></blockquote></div><br class=""></div></div></div></body></html>