Was there another instance of Plex server installed on this machine before? And if so, is it possible that it had “Secure Connections” set to “Required”?
Were the Plex registry data imported from a different Plex Server machine? (i.e. was the installation moved from a different machine?)
Was the system drive re-used from an older machine, or was the Plex data folder copied/moved from an older machine?
Yes. CGNAT, however I’ve been able to at least REGISTER from a CGNAT before because I then just connect to the device locally so the CGNAT never really mattered.
Was there another instance of Plex server installed on this machine before? And if so, is it possible that it had “Secure Connections” set to “Required”?
I initially installed Plex Server from the Windows App store and saw it had installed 1.40 (or something similar) instead of 1.43, so I uninstalled it before I even registered and downloaded the 1.43 directly from Plex
Were the Plex registry data imported from a different Plex Server machine? (i.e. was the installation moved from a different machine?)
No. Brand new install, nothing migrated from any other device.
Was the system drive re-used from an older machine, or was the Plex data folder copied/moved from an older machine?
No. Brand new device, Plex was maybe the third application installed after powering on.
Then you should change that, The hosts within the IP range for CG-NAT are not assumed to be able to freely communicate with each other. Plex Server behaves differently if it’s situated in a network which does not use a private IP range.
I don’t understand why that would affect the initial registration of the server. I installed the Plex Client on my server to see if I could still “see” it to connect with even if the registration failed, and it doesn’t show up when looking for the server from the same computer.
Ultimately, the server will be on the same internal subnet as my other devices. I’m just trying to get things connected and working while I have it connected to the internet before moving it to a closed, internal subnet.
Your current network configuration does not comply with standard networking practices and will likely lead to problems in the future. According to RFC 1918, specific ranges of IP addresses are reserved for private use within homes and organizations. These are:
10.0.0.0/8
172.16.0.0/12
192.168.0.0/16
Instead of using one of these reserved ranges, your network is configured with 1.1.1.0/24, which is not a private range. In fact, this block belongs to Cloudflare and is part of the global public address space. Cloudflare actively uses this range, including 1.1.1.1, which serves as a widely used public DNS resolver.
By assigning addresses from this public range internally, your devices may experience conflicts, routing issues, or connectivity problems when communicating with the internet. To ensure stability, compliance, and proper functionality, the network should be reconfigured to use one of the RFC 1918 private ranges.