App.plex.tv is unable to connect to "SHIELD Android TV" securely

Server Version#: 4.57.4
Player Version#: N/A
Getting error App.plex.tv is unable to connect to “SHIELD Android TV” securely
However I can access it directly on private IP address.
Secure connections setting is on “prefered”

When checking the logs I see the following:
CERT: Error acquiring new certificate: Failed to upload CSR: 429, <?xml version="1.0" encoding="UTF-8"?>

Probably won’t be of much comfort for you, but I had a similar issue yesterday after the server app was updated. I my case however when going into the settings for the server on the Shield, the server section was empty. I tried forcing the client and server apps to stop, then clear the cache, plus multiple reboots. No joy. My suspicion then was that the server update either corrupted the database or made it no longer able to be read. I then forced both the client and server to stop, then removed all updates. I then updated both to the latest versions, before starting the client app again. This meant I had to start from scratch. After the install finished I found I could access the server via the plex web app but not directly from a local workstation. I then was able to go into the server settings on the Shield itself and enable insecure local connections (which was disabled by default). My suspicion is now that the update somehow broke secure connections. In my case this prevented anything from connecting to the server up to and including from the webapp or localhost. So, although the server was actually running, nothing could connect to it. Now maybe there would be some way of editing a local file to change this, but again the ‘fix’ for me was a reinstall.

You are in perhaps a better state as you can actually see your server settings - I’d try changing it to insecure for everything, then reboot, then change it back to what you want. This might reset things…

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