However, if you can get away with some downtime, you can instead notify your users of a planned outage, shutdown, update everything, and startup again. This eliminates several steps of the process, which has the added benefit of reducing the number of places where something can go wrong.
To put this in context: say you guarantee 99.9% uptime - that's still 43.2 min / month of downtime available to you! You can update quite a lot of machines / database rows in even 10-20 min, making this viable in many cases. (Obviously there is a scale threshold past which this is no longer viable, but if you're at that threshold you can probably also spare the engineering effort to go the zero-downtime route!)