Hello @wfrmitstaff,
I was thinking about this all week after reading your question. It would be helpful to be able to temporarily support self signed certs for testing purposes (Not a production environment). One idea i had that may solve this for you is to append your cert crt to the wp-includes/certificates/ca-bundle.crt bundle. I think it will work, except when WordPress updates it will overwrite the cert with its own version, but it is a way to temporarily get your self signed cert to work.
Unfortunately there is no way to globally override the wp-includes/certificates/ca-bundle.crt without actually editing every call that is made to the ‘request()’ function in the class-http.php file. You could edit that source as well, at that point you could simply hard code ‘sslverify’ parameter to false.
For anyone else reading this, you would only want to do this in a test environment, not production.
Thanks,
Angelo