How to delete songs from iPod (5th generation)?

Hi Super Moon,

I see that you're looking to remove some songs on your iPod to make room for new content to sync over. I'd like to help you remove these songs from your device. To easily manage your content, I'd recommend using the "Manually manage music and videos" setting.

Please follow the instructions here to make sure this setting is enabled:

If you can't manually add or remove content from your device

Check to make sure that the "Manually manage music and videos" option is turned on:

1. Connect your device to your computer.
2. Open iTunes. Make sure that you have the latest version.
3. Locate and click on your device.
   
4. In the left sidebar, click Summary.
5. Scroll down to the Options section.
6. Click the box next to "Manually manage music and videos."
   
7. Click Apply.

Once you've done this, select your iPod from the iTunes sidebar. If you need to enable the sidebar in iTunes, you can do this using View > Show Sidebar. Click the disclosure triangle next to the iPod, then choose "Music" from the indented list under the iPod. This will show you all of the songs that you're currently storing on your iPod. From here, you can select the songs that you no longer want on the device, then press the delete key on your keyboard to remove them.

The steps quoted above were taken from this Apple resource:

Move content from iTunes on your computer to your iPhone, iPad, or iPod touch - Apple Support

Cheers!

Hello Super Moon,

Since you're not able to remove the songs normally, I'd recommend that you follow these steps to restore your iPod back to factory settings:

Restore your device to factory settings

1. Open iTunes on your Mac or PC.
2. Connect your iPhone, iPad, or iPod to your computer with the cable that came with your device.
3. If a message asks for your device passcode or to Trust This Computer, follow the onscreen steps. If you forgot your passcode, get help.
4. Select your iPhone, iPad, or iPod when it appears in iTunes.
5. In the Summary panel, click Restore [device].
   
6. Click Restore again to confirm. Then iTunes erases your device and installs the latest iOS or iPod software.
   

Use iTunes on your Mac or PC to restore your iPhone, iPad, or iPod to factory settings - Apple Support

After the restore is complete, you can then sync the desired content back to the iPod and test to see if any issues arise.

Take care!

See Recover media from an iPod. Everything that is on your iPod ought to be in your library so that if the device is lost, stolen, damaged or becomes corrupt and needs restoring you are in a position to restore or replace it.

tt2

As long has you have all the media in your local library now you can listen to it on your computer. See Corrupt iPod Classic, the break up large transfers method there may help repopulate the device.

tt2

See my user tip Recover media from an iPod. You have the files, but they need to be added to iTunes which will hopefully find all the metadata that is still inside the files and can then group them properly by artist and album. Once they are in iTunes you use it to copy the tracks back to the device, not Finder. Note make sure your folders and tracks are not hidden if you are going to use the Automatically Add to iTunes folder to add them to iTunes since when testing (at least with Windows) I discovered that iTunes would discard hidden files instead of adding them to the library.

There would have been an opportunity to extract playlists from the device too, but that was lost when you restored the device before preparing everything in the library. 😟

tt2

A playlist is an ordered list of track references. The same track can be added to multiple lists without taking up more space. Deleting a playlist from a manually managed device won't delete the songs it is comprised of. You should be able to select On My Device > Music and then delete individual items from that location. If that really isn't working to reclaim used space then that would suggest that something has gone with the file management system on the device. The usual approach would be to wipe out the device and reload the content, but that presupposes you have all of the content in your main library. If you don't the link I have provided shows how to recover all of the media into the library so that you are in a position that wiping the device and reloading it becomes a practical proposition.

tt2