I am having exact same problem on a freshly installed latest version Roon Server on Mac Mini running OSX 10.12. At first I can connect and set up the server, then a short while into the scanning process it goes into a loop: Status switching from Started --> Not responding --> Error --> Started --> …

New install - Cannot connect to RoonServer

wizardofoz (Mr Fix It aka The Wiz) November 10, 2017, 1:29pm 7

I have had issues with Roon crashing on scanning a bad file (DSD 512 in my case of a download site as a demo IIRC) there was a thread on this. it should be findable in the logs.