[zakk]

It’s very cool, but every update of mac OS resets it! After a while I didn’t bother to reactivate it…

Is there a permanent solution, that does not involve cron scripts or other hacks?

[blinkingled]

iTerm 2 password manager is a close no hacks required solution that's slightly more involved but not all that much - add your password and on sudo prompt hit cmd+shift+f, touch id and enter.

The touch id part is once per iterm session so overall it's not too bad and reasonably secure as it uses built-in keychain to store passwords I think.

[irusensei]

I think there is a filesystem extended attribute that marks that file as part as the rootless system. If you exclude that attribute it might prevent it from being overwritten. I haven't tested it tho.

[inopinatus]

Just go with that. Far from being a hack, converging Unix-like system configuration from scripts run out of cron is downright mundane.