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iTunes for Windows Tips

Itunes For Windows Tips

I've been busy converting CDs and cassette tapes to digital format. Because I'm in the Apple universe, I use iTunes to sync my music from my computer to my Apple Devices. I ad to to research and re-learn some things I had forgotten about iTunes.

Apple is replacing iTunes with other apps on Mac and mobile devices. However, iTunes is still the app for Windows computers. I assume Apple will eventually replace it with a new app, but I've been unable to find projected dates.

  1. Update iTunes to the latest version. If you have the app installed on your computer, then you’ve likely been notified of updates.

  2. Open iTunes. If there is no menu across the top of the screen (File, Edit, Song, etc.) try pressing Ctrl+B to make the menu visible.

  3. If you place a CD/DVD into your CD/DVD drive with iTunes opened, iTunes detects the disc and opens a window for importing tracks. I noticed no check boxes available to select which tracks I wanted import. From the menu, I selected Edit>Preferences>General tab and clicked List view check boxes in the Show section.

  4. While in Preferences, I clicked the Advanced tab to verify Keep iTunes media folder organized and Copy files to iTunes media folder were active. This causes iTunes to organize your music by album, artist, disc number, track number, and title automatically. Songs, etc. are placed into the iTunes Media folder.


iTunes will often define a CD with multiple artists and various songs as a Compilation. If you like this, then there's nothing you need to do. I dislike it because

I prefer my music grouped by artist in the iTunes media folder.

If Compilations are enabled, iTunes creates a Compilations folder and corresponding album sub-folder in its media folder. This results in some music by a specific artist being in a folder named for the artist and album and other music by the same artist located in the Compilation>Album Title sub-folder. Compilations made it more difficult to find songs by particular artists in Windows File Explorer. I had to search folders named for the artist and also sub-folders of the Compilations folder for a particular artist's music.

To disable Compilations when importing CDs, select all the songs (Ctrl+A), right-click and select Song info or Get Info and deselect the “Album is part of a compilation…….” checkbox near the bottom of the window to prevent the CD being imported as a Compilation.

To remove existing Compilations in your music library, back up your music library. Then click a song and press Ctrl+A on the keyboard. Right click anywhere in the highlighted area, click Get Info, Click Edit items when asked if you want to edit multiple items, then deselect the “Album is part of a compilation……” checkbox. Please note: iTunes will automatically begin creating individual artist folders if they don’t already exist, or moving songs into existing artist and album folders. This will take time, depending on how many Compilations folders and songs exist.

Column Headings

You can sort your music by clicking on various column headings in the library. The headings act as toggles and will switch between sorting in ascending or descending order. You can add/remove column headings by right clicking any heading and selecting or deselecting headings from the opened window. You can rearrange column order by dragging a column heading left or right.

Finding Duplicates

Click the File menu, hover over Library, then click Show duplicate items. Just above the column headings and midway across, you'll see All and Same Album options. Choose the appropriate setting for your needs. I've found Same Album displays many fewer songs than All, obviously.

You can still sort by column headings in this mode. If you find duplicates, then you can choose to remove them or keep them. Some versions may have better quality than others because they were imported from a better source – CD versus tape, for example. Some may be in a different format, MP3 versus iTunes’ AAC format. And, some may be duplicates because you lost track of what you’ve imported – easy to do when importing from 100+ CDs and tapes.

When you're finished dealing with duplicates, click the Done button in the upper right corner.

Find Lost Files

Sometimes iTunes will lose track of files, or you may accidentally delete songs or other files. This tip relies on the fact that iTunes will not add missing songs to a playlist.

The steps are:

  1. Click the File menu, hover over New, then click Playlist or, press Ctrl+N.

  2. A new Playlist list titled Playlist appears in the playlist section of the left pane. It is highlighted so that you can immediately type a new name or press Enter to accept the name “Playlist.” I suggest naming it something like “Found” or “Exists.” Whatever name you choose remember it.

  3. Click a song in the library, then press Ctrl+A to select all songs.

  4. Drag the songs onto the newly named playlist.

  5. Go to the File menu, hover over New, and click Smart Playlist or press Ctrl+Alt+N.

  6. You'll see three boxes on the second row of the window that opens.

  7. In the first box, click the arrow and choose Playlist. In the second box, choose “is not.” In the third box, choose the name of the playlist you used in Step 2. If you named the playlist in Step 2 as “Found,” then left to right the boxes will contain "Playlist," "is not," and "Found." You are telling iTunes to find all songs that are not in the 'Found" playlist.

  8. Click OK. At the top of the screen, you'll see this new Smart Playlist selected and you can give it a new name.

  9. When you click on this new Smart Playlist, you will see songs that iTunes could not find.

  10. Now the fun part - locate the missing files, begins.

  11. Click on a missing song and a box will open with Locate as an option. Click it and navigate to the missing file. If you still have Compilations enabled, don’t forget to look in the Compilations folder for the file. You can also use the Windows File Explorer app, whihc is opened when you click Locate, to find the file. type the first few words of the song name into the Search box in the top right corner.

  12. If you cannot find the missing file, then you may need to re-import the file from CD or tape, or purchase it online.


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