As PeterT said, it sounds like bug he reported. It seems to be related to using a plugboard to change the title. I've seen it on and off for a while, but I haven't been able to get it to consistently break. For me, the first time I reconnect the Touch after putting a new book on it sometimes doesn't get marked as on the device. But, the next time it does. PeterT's shows that for some books it never matches.
In case it is something about the title, could you tell me exactly what the title is in calibre and in the Glo. If the plugboard is changing the title, I need the plugboard definition and what is in the metadata fields added to the title. With this, I should be able to create a test case that hopefully breaks for me as well.
If you see an example that doesn't have a plugboard modified title, that would be good to know as well.