Currently Being ModeratedMay 13, 2013 10:04 AM (in response to Jeank128)
If the songs are already showing in your iTunes music list, youc an either 1) Drag and drop the songs onto the iPod shuffle icon in the side bar, or 2) Click on the iPod in iTunes and click the Music tab and check the "sync music" option and click apply.
Currently Being ModeratedMay 13, 2013 12:59 PM (in response to Jeank128)
If your shuffle is 3rd or 4th (current) gen, here's how to use the automatic syncing approach, which is often more convenient than the manual method. You probably need to set up (or update) the shuffle's Music tab in iTunes.
Select the shuffle in iTunes. There is a row of "tabs" (starting with Summary). Click on Music there. This is the Music tab, where you tell iTunes how to sync your shuffle.
Check the box for Sync Music. If your entire iTunes music library fits on the shuffle, you can choose to sync Entire music library (and skip to next paragraph). Otherwise, choose to sync Selected playlists, artists, albums, and genres. Below that, create a selection of songs to sync to the shuffle. For example, if you want to keep it simple, you can create a new regular playlist in iTunes (call it "iPod Songs"). Put all songs you want on the shuffle on that playlist (including those recent downloads). On the Music tab, find and checkmark that one playlist under Playlists.
When you click Apply, the selection of songs on the Music tab syncs to the shuffle, replacing its existing content. Going forward, any changes to your iTunes music library, related to the Music tab settings, sync automatically the next time you connect the shuffle, or when you click the Sync button. So, if you have a playlist with your "iPod songs," just update that playlist (add and remove songs) whenever you want; iTunes syncs the same changes to the shuffle at the next opportunity.