Duplicate files?

the only time i've experienced something like this was with TV shows. iTunes does not separate one TV show into separate "Season" folders, so, for instance, if a TV show does not give specific names to its episodes, and you name them "Episode #__", some will get overwritten if there are multiple seasons. If you create "Episode 1" tagged as Season 1, iTunes will put it in ...iTunes Music/TV Shows/show/Episode 1.m4v. If you then create an "Episode 1" and tag it as Season 2, iTunes will put it in the same directory with the same file name, thusly overwriting Season 1 Episode 1.

so, it's not exactly what you're talking about, but iTunes can do some funny things.

 

delete duplicate files

I was in a trouble when i downloaded some songs to my iTunes library that already contain the same songs but i didn't remember so its a huge duplicate songs in my library then i use a third party application called Duplicate finder 2009 to delete duplicate iTunes from my iTunes library. it says it can delete duplicate files or move them. it has a great features like instant preview that allow you to select tha file before deleting them or move.

 

i have the same dilemma with this duplicates problems and i had enough, so first i just delete the whole iTunes library then search and remove the duplicate using "Duplicate Files Deleter" 'because it seems the only tool that works for me then after it finish, i let iTunes scan my drive and add the songs.