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Solved ! If anyone else has issues with Roon losing connection to audio device, what seems to have worked for me is to adjust the Resync Delay in Roon's device setup to some value greater than 0ms. Its was not an issue with the Holo Red streamer or the DAC. See attached screen shot. There are many other things that can also cause this problem so your solution may be different.

This playing timeout is it intentional to get you to buy the target? Now I see, I only have to restart the target to get it to work. I am still planning to purchase the diretta target. Will that resolve this issue?

I have a Holo red and Cyan 2 and I have the same issue. Plays for about 25 minutes then stops. Then I have to restart host and target via Gentooplayer. If I were not do the noticeable sound improvement, I would give-up and pass on Diretta. I have a rasbPI 5 as my host. Im using Gentooplayer and Roon, no Hqplayer