Can you point to or write up a blog post with a proof of concept?
https://github.com/FiloSottile/mkcert
https://turbofuture.com/internet/Intercepting-HTTPS-Traffic-...
[Edit: Now that I think of it, I’m not sure if Squid is really required...]
From: http://www.chromium.org/Home/chromium-security/security-faq#...
"Chrome does not perform pin validation when the certificate chain chains up to a private trust anchor. A key result of this policy is that private trust anchors can be used to proxy (or MITM) connections, even to pinned sites. “Data loss prevention” appliances, firewalls, content filters, and malware can use this feature to defeat the protections of key pinning.
We deem this acceptable because the proxy or MITM can only be effective if the client machine has already been configured to trust the proxy’s issuing certificate — that is, the client is already under the control of the person who controls the proxy (e.g. the enterprise’s IT administrator). If the client does not trust the private trust anchor, the proxy’s attempt to mediate the connection will fail as it should."