Almost a year later and I'm struggling helplessly with this exact problem. I've tried a jiggler, but not working. I've tried setting the chromebook accessibility to move the mouse, no luck. We can get either chromebook to stay open, but not connected. The chromebook that we're trying to run remotely using remote desktop keeps timing out - unless someone attends to it, so NOT unattended. Tried some free trials of download remote programs, but they don't seem to run on the chromebook. So frustrating. Is this really a dead end?