How do I put my purchased song on from itunes on my ipod? It will not work no matter what I try. Apple suuport is "closed" right now. This will be my last purchase.

I'll assume you have the current (4th gen) iPod shuffle.

The latest version of iTunes may hide the sidebar. To show the sidebar, from the menu bar, under View, select Show Sidebar.

In the iTunes sidebar, select the shuffle under DEVICES. Over to the right, there is a row of "tabs" (starting with Summary). Click on Music there. This Music tab is where you tell iTunes how to automatically sync songs to the iPod. Here's one easy and convenient way to set it up...

Create a new playlist in iTunes. You do this by clicking on the plus sign (then New Playlist) at the botton of the sidebar. Name it something like "iPod Songs" (or whatever you want).

Up above (in the sidebar), ciick on Music under LIBRARY. From the list to the right, drag ALL of the songs (including that new purchase) that you want from the Music library to that new playlist. You can keep the number of songs small for now, just so you know how this works...

Go back to the shuffle's Music tab, and set it to Sync Music. Below that, choose the option to sync based on Selected playlists, artists, albums, and genres. Below that, ignore everything except for the list of Playlists. Find and checkmark ONLY that new playlist with the songs you want on the shuffle. When you click Apply, all of the songs on that playlist sync to the shuffle.

NOTE: If there are songs on the shuffle already, they are replaced by the selection on the Music tab.

Going forward, to update the songs on the shuffle, just update that playlist (add and remove songs). The iPod does not even need to be connected. The next time you connect the shuffle (or click the Sync button), all changes since the last time sync automatically.

This document has general information about loading content on shuffles, including doing it manually and with the Autofill feature.

http://support.apple.com/kb/HT1719

If you have any specific questions, please post back.

The plus sign (for New Playlist) is "at the bottom of the sidebar." You are just adding the regular playlist to your iTunes library, not to the iPod (at this point).

If you checkmark Sync Music, the choices below will no longer be grayed out.

This all seems like way too much work for what seems like should be a simple process.

It is more work to set up, but A LOT less work to maintain. If you want something that is simple to start, but more of a hassle going forward, use the "manual" method described in the linked document.

If you want to just drag the song to the shuffle, you need to use the manual method, Syncing music manually to iPod shuffle, in the linked document.

Basically, go to the iPod's Summary tab. Check the box to Manually manage music. Apply the change.

Drag songs (from iTunes Music library) you want to the shuffle in the sidebar.

Stop being so melodramatic... 🙂 It doesn't help me want to help you...

The new playlist should appear under PLAYLISTS in the sidebar, not under LIBRARY. This has nothing to do with the iPod; you are just adding songs to a playlist, which is a common iTunes task. Try adding some other songs to the playlist, if this new song has some odd issue.

Select Music under LIBRARY. Over to the right, use the Songs view (so you get a plain list of songs).

Make sure you can see the new playlist (under PLAYLISTS) in the sidebar (scroll sidebar if needed). Do NOT click on the playlist.

From the iTunes Music library list, select a song (or songs) and drag (with a click-hold) the song to the playlist and drop it there. Alternately, if dragging "is a drag," right-click on the selected song (or songs) and select

Add to Playlist -> (select the playlist)

In the sidebar, click on the playlist to check if the song or songs are on it now.

So, are you generally able to add songs to playlists? Again, this has nothing to do with the iPod at this point.

(I'll comment on the manual iPod attempt in a separate post.)

For dragging songs to the shuffle manually, are you sure that it did not add the songs to the shuffle?

Select the iPod in the sidebar, and click the small triangle next to the shuffle name (to the left) to drop down its content list (indented under the shuffle). Click on Music there. To the right, is the list of songs on the shuffle. Are any of the songs you just dragged to the iPod on that list?

Actually, the purpose for creating the playlist was for automatic syncing, not manual loading, but you CAN drag the whole playlist to the shuffle. Good idea... 🙂

So, you're saying that this new song appears fine on the playlist in iTunes. However, after you drag the playlist to the shuffle, all of the songs on the playlist are on the shuffle now, EXCEPT for that one new song? You don't get a message window with an error or explanation?

So, what's so special (or faulty) about that one new song?

Since it's an iTunes Store purchase, you can try re-downloading it (at no cost). On the iTunes Store Home screen, look under QUICK LINKS for Purchased. Click it to go to the Purchased screen, where you can re-download previous iTunes Store purchases. Make sure that new song is there. You won't be able to re-download it, if it's already in your iTunes library. So, click on the Music library in the sidebar, and find that song. Delete it, including sending the song file to the Trash.

Now, go back the the iTunes Store Purchased screen. Find that song again. You can re-download it now; click the cloud button to download.

Try loading it on the iPod again. Hopefully, it will load this time...