I&#x27;m not sure about OpenVPN, but the only time you&#x27;d need to disable rootless for Homebrew is to create &#x2F;usr&#x2F;local if it doesn&#x27;t exist.<p>&#x2F;usr is write-protected, &#x2F;usr&#x2F;local isn&#x27;t. But if &#x2F;usr&#x2F;local doesn&#x27;t exist you can&#x27;t create it. This only affects <i>upgrades</i> to 10.11 where &#x2F;usr&#x2F;local didn&#x27;t exist, if it&#x27;s a clean install Apple creates the directory.