iTunes not retaining downloads

The exclamation point (even one without the asterisks) means that iTunes can no longer find the file (for that song) because the file is no longer where you told iTunes to look for it.

So - are you moving, renaming, or deleting the song after you add it to your iTunes Library?

For example:

• • if the files are downloaded to your Downloads folder, you then add the songs to iTunes and then you move the files to the Music folder, that will be why you have a problem
  • if you then delete the file from the Downloads folder after adding it to iTunes, again, that's why you have the problem
  • if you rename the file, or rename the path to the file after adding it to your iTunes Library, again, that causes the issue
• another (different) cause, is that if the files are on an external drive, such as a memory stick or portable drive, and you tell iTunes that they're on that external drive - and you then disconnect the drive, guess what? iTunes has the same issue again - it can't play the song, but this time it's because you have removed the location of the file. Two fixes for this one (see below)

Think of it this way: iTunes is simply a database, your music is not "in iTunes". Instead, you tell iTunes where the file for a song is located and every time that you want to play the song, or every time that iTunes needs to work with that song (to add it to an iPod for example), it looks in the location you previously told it about, for that file so that it can play it or copy it to an iPod.

So - how to fix the existing problem:

• • if you moved it, but you want to leave the file where it now is, go into iTunes and double-click the song to try an play it. In the latest version of iTunes it will tell you it cannot play it and ask if you would like to locate the file (yes, you do). Use that opportunity to navigate to the new location for the file an select it. It should now play
  • if you deleted the file, go into your recycle bin and restore it to its previous location. Then try to play the song again in iTunes. This time, if you have put it back where it was, it should play
  • if you renamed the file, or the path to it, change it back to whatever it was before and then try playing it. It should now work
• if the files were on a portable drive, that you have since disconnected, you will need to copy them from that drive onto your computer. Once you've put them in their final location, then you can use iTunes to locate the file (in its new, permanent location) (this is fix one)
• if you have music stored on an external drive, that you use all the time for iTunes, then that drive must be running and ready to read - and with the same drive letter, before you start iTunes. In other words, if it was drive F when you added music on it to iTunes, it must be drive F every time in the future (this is fix two)

To prevent this happening again:

• if you intend to move files from the download location, do so before adding the file to your Library
• if the files are on a portable drive, that you temporarily connect to your computer, you need to copy the files onto your computer and then add them to iTunes
• once added to your iTunes Library, there should be no need for you to do anything with the files themselves. If you want to change anything about the song, do it in iTunes.