Hi @Daniel_Greenberg ----- Thank you for reaching out. I have made your PM a public topic in the support thread on the community site so we can address this behavior with you 
Continuing forward, please verify that you are still making use of the same Roon setup (see below) and furthermore can you verify if your library location has changed at any point recently.
“I use Roon on a Mac Mini running OS 10.105. I am running Roon 1.3 (build 269). The music library is attached via USB external drive to Mac Mini. I am using my iPad Mini 3 and phone iPhone 6 as remotes. I am also running a remote on an office iMac running 10.12.6. (mid-2010)”
Additionally, can you please tell me if you are seeing anything in “library cleanup”?
-Eric