Can't add tracks to existing playlists using iTunes for Windows11.1.5.5

The tried and true method of right clicking a track, selecting "Add To Playlist" and selecting a playlist no longer works. There's not response to the end of the process. I'm just back in the original view of the library. When I check the playlist, the track hasn't been added. I don't know what the purpose of the "check box" is but I made sure the original track was checked before attempting the add.
(I searched for an existing thread here and on the Web but couldn't find where others have posted this issue.)

TGill wrote:
thanks for the info on the checkboxes. They just seemed redundant to me
If you use this feature, as shown in my previous screenshot, then unticking a song will cause it to be removed from your iPod at the next Sync, but left in your Library. Leave the ticks turned on.
TGill wrote:
"By the way, on the right-click/Add to Playlist, the Playlist Folders are also listed, but you cannot add a song to a Playlist Folder." If that's the case, what function does that option on the menu perform?
The Playlist Folders are a method of grouping Playlists together, making them easier to find. The reason they are shown in the right-click is to make the Playlists easier to find. Look at the screenshot below, all the "Sleep" Playlists are in my "Sleep Time" folder.
TGill wrote:
As to dragging a track to a playlist, what view lets you see the playlists and songs at the same time?
If you have the Sidebar on (CTRL+S), the Songs View:
... and simply drag the song to any Regular Playlist.

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