Likely you moved files to the iPod. Check the Paths of the greyed out files and it should confirm this or otherwise give a clue as to where MediaMonkey is looking for them: https://www.mediamonkey.com/support/knowledge-base/mediamonkey-playback/why-is-music-greyed-out-fails-to-play/

With MM4 I loaded my playlist with contents of one iPod and then added contents of another iPod to the same playlist. Now half of my total playlist is greyed and wont play. What have I done wrong?
tecoma