Server Version#: Version 3.69.1
Player Version#: Version 1.13.9.5456
Revisiting this topic as it’s happening again. Not sure what changed.
The server “SHIELD Android TV” does not allow secure connections.
On the third screenshot, on the left side go downwards to ‘Network’.
Set ‘Secure Connections’ to ‘preferred’.
Reboot the Shield.
Same problem as mine. @OttoKerner I tried setting the secure connection as preferred, required, doesn’t solve the issue. I tried logging out from app.plex.tv and from plex Web, deleting server entry, unclaim and claiming the server again, no dice…
A couple of us in other threads today and in below thread mentioned the same problem
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It’s already set to preferred
Known issue, being worked on.
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There it is
Thanks 
How did you fix this? I’m having the exact same problem.
I just bought the Shield to replace my WD EX2 Ultra server, had a heck of a time figuring out how to add the media (was expecting to see it in the “storage location” only to stumble upon you needed to add via the web interface via PC. That aside, I could have sworn that when it initially setup it was secure, now it is not. I assume this is still an issue (connecting securely)?
This was a known issue that was fixed shortly after. This solved the problem for me.
There are a few things you need to check. For example, DNS rebind protection was a previous problem for me. I had to apply a rule on my router (see screenshot above).
This link might be useful.
https://support.plex.tv/articles/206225077-how-to-use-secure-server-connections/
The issue was resolved shortly after it was flagged. However, I’ve just seen that the problem has appeared again for some people.
I think it’s currently being worked on.
Thanks Revrora, what I don’t understand is that the WD NAS is secure without toying with the DNS rebind protection and the Shield is not, and these are on the same network ( I disabled the NAS when setting up the Shield)
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