Well, I found the the issue but does not tell me why the Trigger stays disabled.
4/14/2015 1:08:01 PM Err Error watching directory (0/60), trigger: If TEST file is created/changed in TEST, fire, folder: \\TEST\, filter: TEST.txt, err: System.ComponentModel.Win32Exception (0x80004005): The specified network name is no longer available
4/14/2015 1:08:02 PM Debug Reconnecting in file trigger: , InstanceId: 41, hashcode: 61964805
4/14/2015 1:08:02 PM Debug File trigger event (RemoveHandlers), InstanceId: 41, hashcode: 61964805
4/14/2015 1:08:11 PM Debug Reconnecting in file trigger: If TEST file is created/changed in TEST, fire, InstanceId: 36, hashcode: 47051292
4/14/2015 1:08:11 PM Debug File trigger event (RemoveHandlers), InstanceId: 36, hashcode: 47051292
4/14/2015 1:08:11 PM Debug File trigger event (AddHandlers), InstanceId: 36, hashcode: 47051292
4/14/2015 1:08:11 PM Debug Reconnected file trigger 'If TEST file is created/changed in TEST, fire' . Directory: \\TEST\, filter: TEST.txt that belonged to Job 'Test Job'