Q: I just downloaded one song and played it on my computer. It is in my music library.  When I went to sync my iPod, this song was missing from iPod.  It is ticked off along with all the others so it should have gone over.  Any ideas?

How are you syncing it to your device? Are you literally hooking it up to iTunes and clicking on the Sync/Apply button? If so, then when you click on the Music option under the device, is the song included in the selected music to sync? Or is the Sync All Music option selected?

Cheers,

GB

OK, after the sync is done, click on the Music option under the Device and see if what is selected for syncing music. You can also set an option up in iTunes to prevent the automatic sync from happening which would then allow you to review all of your Device Sync settings before kicking off the sync. This is under iTunes>Preferences>click on the Devices option at the top of the little window, and then check the "Prevent iPods, iPhones, and iPads from Syncing Automatically".

Cheers,

GB

Do you have Wifi on your iPod? If so, then you can try to download it directly: Open iTunes, click on More, then on Purchased>Music>Not on My iPod, and see if you can see the new song listed with a little cloud next to it. If you do, then click on the cloud to download it to your device.

If you do not see it, then are you certain that the Apple ID you purchased the song with is the same ID that is signed into the iTunes & App Store on your device?

Cheers,

GB

Oh, sorry....I have no clue how you sync music purchased from a different source ....

You might want to post a new question to the Community under the iTunes forum, since your question is not related to Apple Music (which is a streaming service and not related to music in iTunes or syncing at all).  There are a lot of experts in the iTunes syncing process that will probably be able to help....

Sorry I don't know the answer

Best of luck,

GB

You too! Best of luck

GB

Have you tried dragging the song from the songs list in iTunes to the iPod?

If you expect songs to sync automatically, your iPod needs to be set to Sync Music and new songs must be included in the sync selection.  Once a songs is in your iTunes library, its source is not important.  You can confirm if you did the following to set up your iPod.

Select the iPod in iTunes (click its device button on horizontal bar) to show its settings screen in iTunes Window.  Along the left side (in the sidebar), under Settings, click Music.  To the right, the iPod's Music settings screen is shown.  Is the checkbox there for Sync Music currently checked?

NOTE:  If you checkmark Sync Music now, any songs on the iPod that are not in your iTunes library (on the computer) will be lost.

If Sync Music is not checked, checkmark it.  This turns ON automatic syncing.  Below that, if your entire iTunes music library can fit on your iPod, you can choose the option to sync Entire music library.  Then click Apply.  Going forward, iTunes keep your iPod "in sync" with your iTunes music library, so if you add new songs, iTunes automatically updates the iPod with the same changes the next time you connect it (or click Sync if already connected).

Otherwise (still on the iPod's Music settings screen), if your iTunes music library does not fit on your iPod (or you don't want to sync "everything"), choose the option to sync Selected playlists, artists, albums, and genres.  Then, make your selections from the lists below.  For example, you can create one or more playlists in your iTunes library, with all the songs you want on the iPod. When you add new songs to your library, and you want them on the iPod, add those songs to one of those iPod playlists.  Back on the iPod's Music settings screen, under Playlists, find and select (checkmark) those playlists.  Click Apply to sync your selections to the iPod.  Going forward, iTunes keeps your iPod "in sync" with the selected portion of your iTunes library.