I can't understand why waiting for entitlements takes an unpredictable amount of time! I blocked on my development just because of lacking com.apple.developer.driverkit.allow-any-userclient-access and com.apple.developer.driverkit.userclient-access. Apple could do a much better job to support DriverKit development.

I discovered exactly the same problem yesterday and couldn’t believe it. Self signed p12 certs with openssl 3.x can not be imported in iOS/obj-c. After some try and error I found out that even certs made with openssl 1.x can not be parsed with openssl 3.x command line execution. So my decision was to rebuild and reinstall openssl 1.1.1.s and to forget version 3.x. I don’t know if there are more incompatibilities, but only this example has shown me to be carefully with updates of this lib. Sorry for having no solution and just sharing my experience .