Have you ever looked into wp-cli? It was made for this kind of task.

We use the wp-cli with cron jobs such as indexing when we post with API or database-related things. Even with wp-cli we must login to SSH individually. And this doesn't give us the wp-cli option since it is 3rd party zip file. We possibly can get the file, extract, and delete the old plugin with cli, and then enable the last updated plugin with with cli again with a script. Either way, we must create a script or suck it up, go into each wp individually, and take care of it from the backend...

For the future — this use case screams "Ansible!"

As an agency dev, this is the shit they don't think about. In my case, all that would have to be billed or go through pro-bono approval process.

"Just update it!" Until it all goes to shit, and we have to triage the whole mess.

Sorry you are dealing with this, I have spent the better part of the weekend trying to get them to understand this was inevitable.

Devs: "Don't deploy on Fridays" A8C/Matt: "We will deploy on SATURDAYS"

We finished nearly half. Urgent ones are done but I need to spend another 5-10 hours tomorrow. Today really sucked.