Here is the Build

Large deployment
Filr VM =
Search Appliance =
DataBase = MS Sql server 2008

Mac el capitan
Filr Client - 2.0 (236)

When my mac is first booted, the filr client work great. Files that have never been downloaded / opened on the device open right up when double clicked. After some time, I will double click a file, and the application (any, ms office, picture viewer, text editor, etc...) will report, "Cannot open file". If i right click and "Make available Offline", the file will open perfectly. A reboot of the machine will get everything working normal again.

any suggestions?