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> Apps like the Wireguard GUI don't have access to necessary system APIs outside of the app store

Wait, on macOS? You’re saying the store gives you extra permissions there?

Yes: https://lists.zx2c4.com/pipermail/wireguard/2019-February/00...

These links may help you with your issues.

https://apple.stackexchange.com/questions/72145/can-i-instal...

https://apple.stackexchange.com/questions/42353/can-mac-app-...

https://apple.stackexchange.com/questions/59479/can-mac-app-...

Command line automation isn't the issue I'm having, the issue I'm having is being able to download without making an Apple account.

Sideloading would be helpful if Mac app store apps were made available as sideloaded apps anywhere. But I'm going to hazard a guess that Wireguard would not be permitted to provide those downloads -- I haven't been able to find a download link anywhere. And I'm seeing conflicting information online about whether or not sideloading even works for some apps unless the Apple IDs are shared between computers.

I suppose that I could try to compile the Wireguard app from source, but for all I know, running XCode will require an account as well.

All of these solutions are less work than manually managing the network interfaces myself. It's just kind of crappy that a privacy-oriented company is forcing me to do so. I shouldn't have to outsmart my Mac to get work done.

The interplay between iOS/macOS as “secure” operating systems and Wireguard implementations of “secure” networking on the aforementioned platforms really puts proof to the lie, as to what makes for better security outcomes and implementation stories and for whom.

Yeah if they practiced what they preached you could go to the apple store, pay cash for your laptop. Then once home if you wanted some paid apps you could open up appstore over your super high tech vpn (or even tor browser) path with digital currency and download your app without apple ever knowing who you are. That is the ideal, even better would be to let me order the old fashioned way with a money order with a fake name and address on it and buy the app that way with a randomly generated UUID than I put in with the money order.

I would love a way to anonymously purchase apps, but I'm not even asking for that much accomodation.

I would tolerate giving Apple billing information to purchase an app. I don't understand why I need billing information to download a free app that doesn't cost any money. There's no transaction for Apple to verify.

And I don't understand why I need to give Apple a phone number of any of this.

I'm not even asking for an ideal world, just a very slightly less crappy one; Apple objectively does not need my phone number to let me hit a download link. That serves no purpose, it's a completely unrelated step to the task I'm trying to perform.

I read the requirement as not applying to free apps. You can either require people to give you info to monetize or you can charge a fee, but not both.

Maybe, but this computer cost money, so even if that is their requirement Apple is still violating the spirit of their own rules.

I have to pay money for a piece of hardware and give a bunch of personal information to Apple, just to download a free app on the hardware that I paid for?

I do tend to agree with this idea. People constantly make such arguments talking about Android being free hence "you're the product". But people actually paid hundreds of dollars to get that Android phone, so it's not unreasonable at all to be irritated that your OS is trying to monetize you.

Put in fake data and move on with your life?

Fake phone number that can recieve verification codes over SMS and allow me to respond to them?

If you know an online service that provides that without also requiring me to give it a bunch of personal information, please let me know.