Turn on a capture file instead of just using the scroll back buffer. Click on the computers on the putty top left window frame, choose Change Settings and go into Session logging.
While we debug this it might be easiest if you disable the builtin web server and instead run the attached utility. Its a standalong version of the webserver, which makes it easy for you to see requests coming into the PC for files to play.
Hopefully when you try again you'll see a request for 'D:\Videos\MVP000~1.PLS' or something similar.