Yeah it is certainly a tension between designing for your aunt and for power users. I do think simply making your posture configurable with sensible defaults for the masses would go a long way toward quelling my unease. It’s the “because there are 100 aunties and one of you, sorry, you must be like your aunt” that’s frustrating.

Re TLS: I’m referring to the encrypted server cert. It breaks inspection middle-boxes since they can no longer dynamically generate a response certificate on the fly. I’d just like the ability to say “hey I actually run and trust my middleware, TLS please run in proxy mode” even though I also agree with the new TLS behavior as a good default in general.