Why does the Organize Library box in iTunes keep unchecking?

Every Time I open iTunes or even just go to the Library Tab and click Rganize Library it seems the box is always unchecked and I keep repeatedly check it why does it not stay checked and is iTunes actually organizing my song files or not


Why does the Organize Library box in iTunes keep unchecking?


[Re-Titled by Moderator]

Windows, Windows 10

Posted on Mar 8, 2025 01:17 PM

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2 replies

Mar 8, 2025 04:47 PM in response to kennethdotsey

Do you mean?

  1. File > Library > Organize Library > Consolidate Files
  2. File > Library > Organize Library > Rearrange Files
  3. Edit > Preferences > Advanced > Keep iTunes Media folder organized


The first will copy any content located outside of the media folder into it. iTunes doesn't check to see if the library is currently consolidated, so that option is always available if you reopen the dialog, even if you only used it seconds ago.


Option two will put music items in a subfolder of the media folder called \Music. This option will be greyed out if it has previously been selected, and it is also the default option for a new library.


The third box should retain your setting, staying checked or unchecked if you revisit that dialog later. If your choice isn't being remembered I can suggest some files that you can delete to reset your preferences.


The other preference that is relevant here is:


Edit > Preferences > Advanced > Copy files to iTunes Media folder when adding to library


If this is checked then there is no need to repeatedly consolidate the library, as all new additions will be consolidated.


tt2

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Why does the Organize Library box in iTunes keep unchecking?

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