I posted a support request when I was setting up a new Roon server. My old setup was a QNAP TS-253A and worked (works) fine. My new setup is a Beelink SER7 (32GB, 1TB & 2TB SSD, Windows 11). Both run TailScale as subnet routers and also exit nodes.
When I setup the new server, I got a “Too many failures, stopping playback message”. I switched back to my QNAP setup and everything worked fine.
I decided to try turning off TailScale on the SER7 to see what would happen and everything then worked using the SER7 server. I then turned TailScale back on to see if it would fail and IT DID NOT.
FYI for others and if anyone has an idea of the specific cause and best practice for avoiding, please feel free to post.