While I agree with keeping core as up-to-date as possible, there is sometimes a situation beyond one’s control that requires the use of older core versions. We have one such legacy multisite (a gem of technical debt) that uses a Headway theme in such a way that updating core past 4.2.13 breaks the site. The Headway themes are no longer supported and updating is not an option as there are breaking issues also with that. While we are in the process of migrating to a new solution, the site must remain live for active campaigns. So yes, it is less than ideal, but it is at the latest minor branch version and plugins are kept updated where possible.
Wordfence 6.3.5 broke this site and I had to manually revert to 6.3.4. The failure here was fourfold:
1. I should not have allowed any plugin, no matter how respected, to autoupdate without first testing it in development.
2. Wordfence did not give their customers advanced notice of the breaking change (i.e. adding a dependency on a function present only in 4.4.0+)
3. Wordfence did not update their WordPress plugin page to change the minimum compatibility from “3.9 or higher”.
4. Wordfence released late on a Friday knowing their support staff are offline for the weekend.
The bottom line is that I now need to disable auto update for this plugin across all my production sites, and manually push updates using Ansible only after first testing in development. Not everyone has this capability or workflow in place to protect themselves.
Wordfence is good at security, but my guess is they are still growing as a development shop. They need to take lessons learned from the DevOps movement and improve in a hurry.