Yes, you are right, and this is a little bit complicated situation.
Our users complain that they can access sites with "wrong" web server setup directly, but behind squid proxy. And there are many sites (including goverment related), which are still wrong, but needed to be accessed.. on the other hand, nobody can force site admins to update to proper config. Here comes in OpenSSL 1.1.1, which is able to handle this situation. And yes, I do not want to allow accept expired certs in squid.
I assume that squid uses pfsense's cert store, but I could not find exact documentation.