If you lost your Itunes Checked songs or you notice that the songs which are checked are not the ones on your Ipod then I have a solution for you! (Can be adopted for Windows but I will be explaining in terms of Os X)

Say you had to reinstall Itunes to fix a bug. You do everything the Apple site tells you and you reinstall everything. You open up Itunes and you find that the songs which are checked correspond to a list of songs which were checked a year ago and if you connect your Ipod now you are going to end up with a one year old playlist. Here is what you do:

This Assumes that (a) you know where all your songs are on your PC/Mac (b) that the only songs which were checked are the ones on your Ipod (or the only songs you care to organize are on your ipod) (c) that you didn’t say No to assumption B and you don’t have the shuffle function enabled in Itunes. (In this case you shouldn’t care which songs are checked anyways)

Since all your songs are still on your computer (AGAIN! assuming that you KNOW where ALL your music is) I recommend you do a quick “Select All” and “Delete”. Then go to the directory where all your songs are and just drag them all back into Itunes. This will assure you that your Itunes Library has ALL the songs that you had prior to doing the reinstall.

First, connect the Ipod to the computer, making sure that you hold down the CMD + Option keys on a Mac (Shift + Ctrl keys in Windows) OR you hustle and cancel the sync operation.

After you have safely connected your Ipod click on your Ipod under Devices, the Summary tab, and then click “Manually Manage Music and Videos“. This will allow you to do the crucial next step.

Making sure that you are still under your Ipod go to the Music section. Edit–>Select All, then File–>New Playlist From Selection. This will create you a new playlist. Name it “You Owe Me” so you know which Playlist is the one you need for the next step.

Right click your newly created Playlist and click Export. Save it to the desktop so you know where it is.

Now goto the Music section under Library. This should be your Itunes Library. Then File–>Library–>Import Playlist–>Import the playlist you placed on your desktop.

Now Edit–>Select All your music from the Itunes Library. Right click any song and click “Uncheck Selection”.

Then Navigate to the Imported playlist. (Should be in the Playlist section in the same name “You Owe Me”.) Edit–>Select All, Right click any song and the click “Check Selection”.

There you have it, you now have all your Checked songs back and your library is back to its former glory.