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For as long as I can remember iTunes used to ask me, when deleting a TV series or movie, if I wanted to delete the file on the disk as well.

Now, the question no longer pops up and the files are not deleted.

Here are the settings:

iTunes settings

How can I make iTunes delete the files themselves when I delete something from the library?

  • Have you confirmed whether movies are or are not being removed from disk regardless of the questions iTunes asked? You can look in ~/Music/iTunes/iTunes Media/ to check. – Iain Jan 13 at 14:41
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    @Iain Yes I checked. Files are not removed (I have to delete them manually) – Matteo Jan 14 at 7:17
  • I've fixed some weird problems like this with iTunes in the past by backing up the database and then removing it, and iTunes rebuilds it. The instructions sometimes change between versions but this looks a lot like what I did the last time. – Iain Jan 14 at 7:21

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