I keep getting the message on iTunes that my Shuffle (which is current on updates) needs to be restored. It is showing up in devices, but when I try to add songs to it, I don't get the little progress bar showing me that the song is being added. ***?

Question

I updated to the new iTunes last week.  Today I plugged in my 4th generation Shuffle to add some new songs.  The shuffle appears in Devices, but when I try to add songs, I'm not getting the progress bar at the top of the screen, so I'm assuming the song isn't being added.  I tried ejecting the Shuffle and plugging it in again, and I got a message that my iPod needed to be restored before it could be used with iTunes -- even though the screen also said the Shuffle is up to date on the software. I finally gave in and restored it, but I continue to get the same message.  When I eject the iPod and try to play it now, I'm getting nothing, and when it is connected to the usb port, the orange light is continually flashing.  I've been trying to figure this out for about 3 hours now, so if anyone could help me, I'd be eternally grateful!

Answer 1

The 1st and 2nd gen shuffles do not have an automatic syncing mode, like later shuffles and the "big" iPods.  It is maintained manually (or by using the Autofill feature).
If the iTunes sidebar (along left side of window) is hidden, from the menu bar, under View, select Show Sidebar.  The shuffle appears in the sidebar, under DEVICES, when connected.
To add songs to the shuffle...  Show a list of songs in the iTunes window.  For example, you can select Music under LIBRARY (in the sidebar) to show your complete iTunes music library list.  Select a song and drag it to the shuffle in the sidebar.  You can do this with more than one song selected.  Alternately, select the song(s), right-click the selection, and choose the command to Add to Playlist -> [name of iPod].
To remove songs from the shuffle...  Select the shuffle in the sidebar.  To the right, it's Settings screen is shown.  Toward the top, where it says Settings, click on On This iPod (to the right).  The list of songs on the shuffle is shown below.  Select the song you want to remove and press Delete on the keyboard.  You can do this with more than one song selected. 
NOTE:  At the bottom of the shuffle's list of songs, there are controls for the Autofill feature.  You can also use Autofill to fill your shuffle from your music library or from a specific playlist.