Or if you want to cover existing users, just ask during the first interactive invocation, when there is no prior user chosen setting (works for new installs too

Or if you want to cover existing users, just ask during the first interactive invocation, when there is no prior user chosen setting (works for new installs too)... pseudocode: choice = no if $brew_prefix/etc/homebrew.yaml: choice = read analytics $brew_prefix/etc/homebrew.yaml else: if interactive-tty and cmd != "--prefix": choice = ask-user "enable anonymous analytics (it helps us!)? Y/N: " write analytics=<choice> $brew_prefix/etc/homebrew.yaml if choice == yes: enable-analytics