Why does iTunes for Windows truncate filenames?

From reviewing other threads, like this one Why does iTunes truncate the name of my MP3s ?, it looks like a ID3 tag version issue.

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.

Windows has a 255 character limit for filenames. That said is it still sometimes possible to bury files deeper than that by accident, for example if higher level folders are renamed. This can cause problems accessing the files.

I don't know why iTunes for Windows imposes the 40 character limit, but if you don't have the "Keep organized" option set you can put things where you want before you import them to iTunes and they will stay as you left them. I used to manually tweak, remove and reimport stuff but these days I have a custom script that renames files according to my rules (different character substitutions, longer paths, certain genre specific folders etc.) and then automatically reconnects iTunes to the files.

tt2

As I said I don't know why iTFW limits segments of the path to 40 characters, however the rule is applied consistently to all parts of the path that iTunes is managing. I started out with an iRiver H140 which took forever to start up in full database mode so I used the file system to access my media. This meant that truncated or mangled text affected how easily I could select what I wanted to listen to. Back in the day I would fix my file structure with Magic File Renamer, remove any broken links from iTunes and reimport. Eventually I got in to scripting which is much more powerful and convenient. It also provides a good way to waste time which could otherwise be spent just enjoying the music. I strongly advise you not to care what your library looks like within the filing system but concentrate on making it perform for you within the application. If you read my article on Grouping tracks into albums you'll see there is the potential for quite enough obsessive organization there before you start worrying about the files themselves. If it really bothers you then download my ConsolidateByMoving script and change the line that reads Std=True to Std=False. This will give you longer filenames and better character substitutions, for example a double quote becomes two single quotes instead of an underscore.

You could also drop a line to iTunes Feedback but I'm guessing they've probably had plenty on this topic over the years and haven't felt the need to change it yet.

tt2

I suppose the point I'm trying to make is that the program works as it is designed to. From that point of view there is no problem to solve. Like many applications it can't work exactly the way every user would like it to. While there is no harm in letting Apple know that you'd like it changed, don't expect them to change just for you.

Their feedback pages promise that your submission will be read, but explicity state that you won't get a reply. You've not been singled out to be ignored, that's just the way it works. If they employed people to respond individually to every item of feedback or ran in-house tech support instead of this user support area everything they make or sell would have to cost even more than it does now.

Having made your submission the options are to live with the software as it works now, find a workaround, or use something else. Use something else doesn't really cut it for me with an iPhone, iPad and some older iPods in the family and, try as I might, I can't live with what I consider to be poor organisation, so I've built my own workarounds. Feel free to use and adapt them for your needs if you wish.

tt2

If the names are "carefully constructed" then why are you letting iTunes manage them at all? I don't. Simply go to Edit > Preferences > Advanced and uncheck Keep iTunes Media folder organised, then redo the import of your library from your original source folders with the full length filenames. Copy these into the iTunes Media folder the way you want them organised and then add them to the library.

tt2

FWIW, I have iTunes running on a PC, which does truncate the file names, and also iTunes running on an iMac, which doesn't. Go figure?

I have spent forever getting my media folder organised, repairing links etc., so not too chuffed that iTunes now wants to arbitrarily truncate file names. Looks like I will have to transfer all my files (500Gb) to the Mac, as I wanted to convert them all from WAV to Apple Lossless, then copy to my NAS - this would seem to be the only way to preserve the integrity of the file names.

NB, I don't allow iTunes to organise the media folder, but it still buggers about with the file names when I create a Lossless copy.

Might look to see what other tools exist to create Lossless copies.

I find that some file names are truncated while longer file names in the same album are NOT truncated. So, it seems to be arbitrary.

The Windows file system imposes a 260 character path length limit. For reasons known only to Apple they have imposed a 40 character limit on each segment of the path that the application constructs, the artist and album folders, and the filename including the file extension. All characters that are invalid in filenames are replaced with underscores. As long as the path to the media folder is shorter than about 130 characters (to allow for \Music\ and other separators in the path) then iTunes won't exceed the permitted path length. OS X doesn't have the same path length limitation which presumably explains the different strategy.

A proportional font may give the wrong impression as to which string is longer than another. An extreme example is shown here:

iiiiiiiiii (10 charcters)

wwwww (5 characters)

In general it really doesn't matter where the media files are stored as long as each application you use is able to find them when you want them. That said I too prefer to see as much information as possible in the file paths. I use a custom version of my script ConsolidateByMovingLong which will preserve all of the detail if possible, has nicer character substitutions and, in my case, also moves certain genres such as comedy, classical and soundtracks into their own folders.

tt2

Years later this is still a thing. We can thank the apologists for creating an environment where apple will never feel the need to address these things.