iTunes does not move files to the correct folder

Firstly, it doesn't really matter where the files are, so long as iTunes can find them. I'd be tempted to ignore the physical location as long as the logical placement in iTunes is doing what you want.

If you choose to move a file by hand iTunes will lose track of it. You can reconnect files one by one, but that can be a lot of effort. The metadata should survive, which it may not do if you remove, move, and then reimport.

I believe the security tab is normally hidden on "Home" versions of Windows. There are tutorials that show how to enable it, but I'm not certain that it would fix the issue of you so, and it won't matter once you move to your new Mac. 🙂

tt2

Thanks again for the reply. I back up my TV shows to a NAS attached to my TV and also to a backup service and after that another hard drive, so for that reason it does matter somewhat as I now have to change my backup routines. Plus, with years of music and videos I have over 2TB of data. It's important to be consistent about their organization and where to find them, especially because of the backup routines. Plus, I expect Apple's software to do what it's supposed to do. I don't think that's unreasonable.

In that case you should submit to iTunes Feedback. I'm somewhat surprised that with such a large gap between the two releases of iTunes 12 this bug hasn't been picked up on. I'm equally committed to organizing my library just the way I want it ( http://samsoft.org.uk/itunes/scripts.asp ) but I'm also concious that I can spend more time curating my library than enjoying it. 😮

I do have a script called ConsolidateByMoving that moves files and relinks iTunes automatically, but I think it needs tweaking to cope correctly with video files that aren't already in the correct media subfolder. As I recall Media Kind isn't exposed directly in the script interface. I've previously used the current path to infer the kind, but I could tweak this to test the current playlists a file is a member of and get media kind from that.

tt2

This issue persists in iTunes 12.1.1.4 64-bit for Windows (sigh).

Thanks to tt2 for providing the fastest way to manually fix your library:

• Go to Edit --> Preferences --> Advanced

  Uncheck "Keep iTunes Media folder organized" and click OK

• Go to Edit --> Preferences --> Advanced

  Check "Keep iTunes Media folder organized" and click OK

After this cycle, iTunes fixes its own library. Why this isn't always done automatically/programatically by iTunes for new media added continues to be a mystery.

This issue persists in iTunes 12.1.2.27 64-bit for Windows. It doesn't look like Apple is ever going to address this.

How annoying. 😕 Have you made use of the feedback channels I mentioned earlier?

In addition to iTunes Feedback you could sign up for a free Apple Developer Connection account and make use of Apple Bug Reporter.

tt2

I have left feedback, but not the developer thing. I'm quite sure people at Apple are aware of the problem, but since it's only happening on Windows and not OS X, it's not a high priority for them. You know it would be fixed straight away if it were an issue on the latter.

I installed iTunes 12.2.0.145 x64 for Windows today, and so far I haven't had this issue. I've added two new TV shows to my library, and after entering the metadata, the folder structure has been organized as it should be - I haven't had to use the usual workarounds.

Perhaps this issue is finally fixed...will report back if my luck turns.

Sounds promising. 🙂

tt2

I have found a solution that worked for me (iTunes 12, Windows). I had a few films that I had imported as home videos, but despite changing the meta tag to film they still remained in the home videos folder on my hard drive.

I tried to use the File > Library > Organise Library menu but the checkbox to organise files in the iTunes Media folder was disabled (I already had the automatic organisation enabled in settings).

1. Open the advanced settings tab (Edit > Preferences > Advanced, you may need to press the alt key to display the menu bar).
2. Uncheck the checkbox "Keep iTunes Media Folder Organised"
3. Press okay.
4. Repeat steps 1 and 2, but this time checking the checkbox again.
5. When you press the okay button a progress bar will appear in a popup (before the settings popup closes, it may appear behind the settings popup), wait whilst your files are moved the their correct locations based on their metadata.

Note: This may mess-up your library file structure if you use anything other than the default iTunes organisation.

Also check that you have "Copy files to iTunes Media folder when adding to the library" checked in the advanced settings tab.

You can check that the files have been moved, by right clicking on a film that was in the wrong place and clicking "Open in Explorer" - it should now open the file in the correct position.

I found that I had to repeat this process every time I add a new film which didn't move automatically.

TL;DR: Uncheck and re-check "Keep iTunes Media Folder Organised"

Indeed, we've been using that workaround. Unfortunately, the latest version of iTunes (12.2.1.16) still doesn't fix the problem. It's better (don't have to use the workaround as often), but still intermittently broken. I've lost hope for a permanent fix.

So iTunes 12.3.0.44 seems to have finally fixed this...I haven't had to use the workaround yet, and it's been installed for a couple of weeks. Here's hoping!

So 12.3.0.44 is still not perfect, but much better than previous versions. I estimate I need to use the workaround about 20% of the time now.