lol
There you go.
The ability of LW to auto transfer files to iTunes for windows users might suffer similar problems Mac OSX users have had for many years; if LW has been very busy & on for a long time, sometimes the transferring stops. Seems the communication gets broken somehow. The answers are to either close & re-open LW, else go to LW's preferences (options I mean), turn option for auto transfer to iTunes off, press Apply button, Then re-enable it again which usually fixes it.