Openfire chat missing features when clients log in to multiple devices under the same account

I have Openfire set up with the monitoring service plugin which we have been using with Pidgin on the desktop. One of the things I've noticed is that when I sign in to another computer on the same account, I do not get a history of recent messages (which I thought the monitoring plugin was supposed to provide).

The other thing that doesn't seem to be working right is when I am logged in to two computers simultaneously (using the same account). I expect to see chat messages showing up on BOTH devices so I can go between machines, which again is something I thought the monitoring plug was supposed to provide.

The settings I believe are related are under "Offline messages" which I have set to always store, and retain for up to 30 days. Should I bee looking for anything else?

I have been using Pidgin with XMPP on Google for years, so I know both the XMPP protocol and the Pidgin client are capable of handling this functionality. I've been digging around trying to find a solution, and see a lot of things claiming Pidgin is the culprit here, but those messages are a decade old. I can't seem to find any information on the subject for Openfire newer than about 2016.

I'm hoping there's a setting I need to change or another plugin I need to add to get both of these features working on my server? I really love the software otherwise but this seems like a really basic function that should just work, and I am hoping someone can point me to whatever I'm missing.