Thanks for taking the time to reply, but I have to say, your random guesses are way off base and borderline disrespectful. I've done tech support for many years, so I can appreciate your attempts at triage. However, given that this is a repeating problem, your immediate pivot to something that's obviously not the problem is bad triage, and bad troubleshooting.
The "Remember Me" checkbox gives a cookie to the browser, and that cookie is what keeps you logged in, aka lets the server remember you. This is how things were built because HTTP )and therefore HTTPS) are connectionless protocols. This is why I explained my setup as far as cookie management, and that older instances of Octoprint are able to successfully negotiate the cookies properly. This also shows that my cookie management is not the issue. I also brought to your attenion that this has been a reocurring problem. In today's post, I found several reports and have linked them below.
To address your question, my "router" is a pfSense box, which is a computer running an enterprise-grade purposebuilt BSD distro that acts as a firewall, and has all the normal "router" functionality. Yes, each instance of Octoprint has it's own hostname. You could have inferred as much by the fact I told you the others all worked fine.
I set up a new instance of Octoprint yesterday, and both of the new ones (OctoPrint 1.10.3 Python 3.9.2 OctoPi* 1.0.0 (build 2024.11.05.092907)) had the same issue again today.
I suspected the issue might be with the local time of the Pi, and it's certainly way out of whack. I'm not sure why NTP is missing, but that explains why it's not working. If you don't know why that's relevent, I suggest that you keep digging, because that's probably the root of my problem.
No Longer 'Remember Me' auto login
Da_Hai_Zhu September 18, 2019, 1:42am 1
https ://community.octoprint.org/t/no-longer-remember-me-auto-login/12098
Octopi.local asking to log in every time even though I mark "Remember Me"
Jan 2019
https ://github.com/guysoft/OctoPi/issues/568
Remember Me not working in 1.3.10
Dec 2018
https ://github.com/OctoPrint/OctoPrint/issues/2971
1.4.0rc* Login sessions not persistent even with "Remember me" selected
Feb 2020
https ://github.com/OctoPrint/OctoPrint/issues/3459
Login Screen - Remember Me doesn't work with Touch UI
https ://community.octoprint.org/t/login-screen-remember-me-doesnt-work-with-touch-ui/8250
[1.40rc3] "Remember me" doesn't stick
Jan 2020
https ://github.com/OctoPrint/OctoPrint/issues/3426
Remember Me fails with http after closing and re-opening browser a couple of times OctoPrint 1.8.3
Sept 2022
https ://github.com/OctoPrint/OctoPrint/issues/4650
Web interface ignores saved password when accessing through a link
Sept 2022
https ://community.octoprint.org/t/web-interface-ignores-saved-password-when-accessing-through-a-link/46741
Why does remember me always forget me?
https ://community.octoprint.org/t/why-does-remember-me-always-forget-me/847
octoprint-systeminfo-20220922140757.zip (276.3 KB)