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I'm not sure about OpenVPN, but the only time you'd need to disable rootless for Homebrew is to create /usr/local if it doesn't exist. /usr is write-protected,

I'm not sure about OpenVPN, but the only time you'd need to disable rootless for Homebrew is to create /usr/local if it doesn't exist. /usr is write-protected, /usr/local isn't. But if /usr/local doesn't exist you can't create it. This only affects upgrades to 10.11 where /usr/local didn't exist, if it's a clean install Apple creates the directory.

kedean 11y ago
That's besides the point. Apple is still restricting what you do on your laptop by having the underlying system preventing you from creating that yourself. The homebrew issue is just a symptom of the restriction.
- hyperpape 11y ago
  To be fair, there is a reasonably transparent way to get around it. It's less convenient than typing "sudo" before a command, but it's not the same as having to bypass DRM or some other scheme that's truly designed to prevent you (the person) having access. What I worry about is my ability to keep up with the details of what I can do when and whether this is a trend that will get worse.