Hello,
I'm pretty new to OctoPrint, so forgive me for my ignorance on the issue. I'm working on setting up a RPi 5 with OctoPrint, but I had trouble trying to log in to the web server on the Pi, so I installed on Windows and got some luck there. The one question I had was, would I need to be able to log in to the OctoPrint web server on Windows with the Raspberry Pi connected, or would I have to be able to log into the web server on the Pi in order to use its capabilities?
Have you installed Ubuntu\Octoprint on the RPi5 ? and can you attach a monitor\Keyboard\network connection and login into the Pi ??
If all working ok, before connecting the printer, then, from your windows machine, in a browser try connecting to the Pi using http://Octoprint-IP-Address(e.g.192.168.0.123) if working you should then get the initial logon screen.
I'd also suggest installing a Bitvise client to SSH into the Pi5 to enable access the the file system & control system.
You don't need to install anything on Windows in order to access your OctoPrint install that is on your Pi.
Please note that the OctoPi image is not compatible with the Raspberry Pi 5 - you should install a regular OS such as Raspberry Pi OS (Lite version will do), and then install OctoPrint afterwards. I can recommend the octoprint_deploy option to set it up easily.
So I did install Octoprint on the Pi, but I wasn't able to figure out the login issues, which is why I installed it on Windows as well. That's why I was wondering if I'd be able to access Octoprint on my Windows laptop and have the Pi connected to Octoprint
That isn't how OctoPrint works. Forget installing anything on Windows, focus on getting your Pi working.