Ok, so I think I figured it all out thanks to Otto’s suggestions. We will have to see, but it seems likely that the root cause has been found. I have an audit policy running on my firewall now to see if the rogue device connects again.
TL;DR version: A TV in our guest bedroom was logged in to Roku with someone else’s account.
Long version: Given the way Otto said Roku works with authorization to Plex, I started looking at all my TVs/devices to see if I could match the name of the device to Roku/Plex. In doing so, I found that someone else’s account was used on one of our TVs for Roku. That means that every time we authorized that TV on Plex it was allowing that whole account access. I even confirmed that was the behavior of Roku devices after finding this.
Once I realized that was not our Roku account, I factory reset that device. I then went in to Plex and reset the password and kicked off devices again. One thing to note is that checking that box didn’t remove everything from Authorized Devices in Plex. I have had this issue before and noted it either in this thread or the Discord thread. I manually went in to Plex after reclaiming the server and removed most devices. There were some that I knew exactly what they are, so I didn’t deauthorize them.
After doing that, I went to Plex on our main Roku TV and logged in to Plex there. Required me to authorize it (QR code to login and MFA prompt). After doing that, the next Roku device I went to for Plex did NOT require me to authorize or MFA. It just connected right to Plex without any login prompt or warning. I confirmed this on a 3rd device. All 3 devices (the first explicitly authorized and the 2 implicitly authorized devices) then showed up in Plex Authorized Devices.
This is confirmation of what Otto was saying about how Roku is account-wide Plex authorization for all devices. This ALSO explains a rogue device. Every time we re-authorized that guest room TV, it authorized for that whole rogue account.
So, I get HOW it is happening, but what I don’t understand is why Plex is allowing this. This seems like a security issue to me. I understand Roku wants to make it “easy” on their customers, but Plex should have security built-in to prevent such a thing. Obviously, it’s a feature request and may already be on the Plex roadmap.
At this point, I think the issue is resolved. I am going to mark Otto’s answer as correct even though I think it needs more context. Still, he was right. Thank you to everyone that responded and helped. I really appreciate it.