As a Mac admin VPP/App Store distribution is still quite finicky. I don’t understand why Apple has to flex and restrict NetworkExtension/VPN apps to Mac App Store. More iOS-ification of the OS.
This is one of the things I dislike most about Apple: even despite the high price I pay for their products and (subsequently) the astronomical profits they make, somehow they seem to be completely unable to simply address these kinds of problems as soon as they pop up and make everyone happy again. It's also in Apple's own interest to make sure VPN extensions can automatically update in case of potential security problems, no? So why they don't just throw enough resources at it to make it work really is beyond me.
There's a lot to like about Apple products but their culture towards addressing problems that affect their paying customers is becoming increasingly off-putting, especially since they have basically been printing money for over ~10 years now and have no excuses to not improve these kinds of things.
Apple can't hire enough devs.
I told an SWE friend of mine at Apple that I wouldn't mind working there - then he explained to me how restrictive it is to work at Apple (e.g. you have to close your GitHub account, you can't do any moonlighting or FOSS contributions: even on your own time, on your own hardware, while on vacation) - I can't work at a place that wants to exert that much control over my personal life. I get that secrecy is part of being an Apple, but it feels the same as how I thought it'd be cool to work for the FBI's infosec team before I learned that they have mandatory regular drug-testing even for employees in states where cannabis is legal.
Apple decided to not hire more.
Apple Inc. has massive profits and they apparently decided that frameworks are good enough and it is not worth to pay more (both in cash - and also indirectly, by less hostile requirements).
[1]: reader decide whether it is a good solution or not
One rule for small, other rule for big.
Apple's overly protective threat modelling/mitigation is a selling point and not a "flex" for me.