Q: My iPod Nano 2nd generation is not working with iTunes

When I plug it in iTunes recognizes my iPod, syncs it, but then the iPod library is grey.

If the iPod's Music list is greyed out, that usually means the iPod uses automatic syncing.  You cannot change anything directly on the iPod, because you are not manually managing content.  You let iTunes manage the content, based on the settings on the iPod's Music settings screen.

Select the iPod in iTunes.  In iTunes 12, click the "device button" on the horizontal bar (its icon looks like the device).  The iPod's "management" screen comes up, showing the iPod's Summary settings view.  Is the box for Manually manage music checked or not checked?  If it's not checked, you are using automatic syncing.  In the iPod's sidebar, under Settings, click Music to show the iPod's Music settings screen and set up (or update) automatic syncing for songs.

After changing a setting for the iPod, be sure to click Apply.

If the iPod is set for Manually manage music, you should be able to add content to it manually (by dragging items to the iPod in iTunes), delete content from it manually (by selecting items on the iPod's list and pressing Delete on keyboard), and drag items to playlists that are on the iPod.  You cannot drag items "off" the iPod into your iTunes library.

If it does not work, you may want to do a Restore on the iPod in iTunes, to give it a fresh start.  This will erase the iPod, reinstall its software, and set it to default settings.  You can then start with an empty iPod, and set it to the manual setting.

Restoring iPod to factory settings - Apple Support

You did a Restore?  As a test, to see if there is something generally wrong with the iPod, set it up to do a small automatic sync.  Select the iPod in iTunes 12, so that you see the iPod's "management" screen.  In the iPod's sidebar, under Settings, click Music.  To the right, check the checkbox for Sync Music.  This enables automatic syncing for songs.  NOTE:  Automatic syncing replaces your iPod's existing content, so if there are songs currently on the iPod that are not in your iTunes library, don't do this.  But if you already did a Restore, it's a non-issue since you've already erased the iPod.

Below the Sync Music setting, select the option to sync Selected playlists, artists, albums, and genres.  Below that, under Playlists, select (checkmark) one playlists with a reasonable number of songs.  Or select one artist under Artists.  Click Apply.

Does that sync the songs in your selection to the iPod?

FYI - I have several iPods that are older than your 2nd gen nano, including a 3rd gen "classic" iPod from 2003 (which connects using FireWire).  They all work fine with the iTunes 12. 

Hi - I had the same problem - even though I have been able to drag and drop music from itunes to the nano always before - this has suddenly stopped happening.

But I just discovered another way to do it.

Make a new playlist on the Nano and open it.

In the top right corner of the empty playlist box you will see a button that says "Add to"

when you click that button you can add any music you choose from the computer to that playlist

I hope that helps solve your problem if you didn't find a way before.

I had the same problem. I had to eject and then disconnect my iPod Nano. Then I had to close and restart iTunes. Now it seems to work. Whew. I almost panicked for a minute there. Love my little Nano.