I feel like the only person in the world that can't download playlists...

Question

I create the playlist. I try to auto fill. It doesn't. How can I get my playlists on to my Shuffle?

Answer 1

That's the way you create a new playlist, although you can also do it (in Macs, at least) by clicking the Add ( + ) button at the bottom of the playlist column.
You do drag songs into them, as you said. Can you then play those songs from that playlist in iTunes? Have you checked the formata of those tracks to be sure that it's one that the Shuffle can use?
I don't know what the "My iPod screen" might be. Do you just mean you selected the Shuffle's playlist in iTunes?
I don't know what the 'first check box' might mean, but it sounds like it's the one called "Replace all when autofilling". If so, why not just say that?
You seem to be saying that it works if it's checked — does that mean that all of the songs on your Shuffle are replaced by new ones, i.e., an Autofill from your selected playlist? Isn't that the same thing that you say isn't happening?
You go on to say that nothing happens if that same box is unchecked. Are you sure that anything is supposed to happen? Is there any room on your iPS for new tracks from the selected playlist?
I don't understand the last question at all. Your playlist won't 'look like' anything at all on the Shuffle, won't have a special icon or anything else .... the Shuffle has no display, for starters. Nothing changes in iTunes, if that's what you really mean.