Alright, so I'm on windows 7 64 bit, but hopefully my question still applies to AskDifferent, considering it is an iTunes issue. I've built a new computer for my girlfriend, and everything went well when transferring her old library. I have one issue. She uses the Keep itunes media folder organized setting on, and it seems that a lot of songs with long names ended up being truncated.

Wouldn't be that big of a deal (despite it being really weird), but we really really want to keep the old playcounts, ratings and paths in each playlist where these songs are used.

So the old path is pointing here:

/D:/Music/iTunes/iTunes Music/Music/Alix Perez/U EP/1-03 Make It Worth (+ DJ Rashad & DJ Spinn).mp3

But for some reason when transferring the music over and letting iTunes take care of it, it managed to turn this file into the following:

/D:/Music/iTunes/iTunes Music/Music/Alix Perez/U EP/1-03 Make It Worth (+ DJ Rashad & DJ.mp3

Is there a way to fix this?

  • This ars article might be relevant; I remember the author talking about filenames being truncated when moving them to ext3 (if you're moving your library to Windows you'll be dealing with NTFS). arstechnica.com/apple/2012/12/…
    – toxefa
    Feb 19, 2017 at 11:04

1 Answer 1


iTunes for Windows truncates file names to 40 characters. You'll notice that your original file name (not including directories) is 47 characters and the truncated file name is 40 characters. Why does it do it? I don't know; I wasn't able to find out.


If you let iTunes "Keep the iTunes Media folder organized" it will use folder and file names with a maximum of 40 characters, inclusive of the extension characters. The following characters are replaced with an underscore. \ / : * ? " < > | and also ; (which is a valid filename character). A leading space or period is also replaced, as is a trailing period for a folder name. Trailing spaces are stripped.

The author of that post has a script that can consolidate your iTunes library while still keeping your long file names. You can find it at http://samsoft.org.uk/iTunes/scripts.asp#ConsolidateByMovingLong.

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