When I first setup WordPress on OpenBSD I followed Michael W. Lucas’s book, “Httpd and Relayd”. Actually, this was my first experience ever setting up WordPress on any server. The steps Michael gave made setting it up straightforward. But, when there was an update to WordPress 5.3 yesterday, I felt a bit nervous. I couldn’t find a howto or tutorial on how to upgrade WordPress in a chroot.
httpd on OpenBSD runs in a chroot. I thought this would prove to be a huge problem but it wasn’t too difficult to update.
In addition to Michael’s book mentioned above, the WordPress documentation on doing a manual upgrade was also helpful.