HT202662: Turn on the menu bar in iTunes for Windows
Learn about Turn on the menu bar in iTunes for Windows
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Feb 17, 2016 7:05 AM in response to vickiefrompaby Kenichi Watanabe,If you are expecting songs to sync automatically, the iPod needs to be set up to use automatic syncing. Alternately, you can load songs manually. I'll describe the manual method, because your ipod is likely to be set (currently) to use manual loading.
First, you need to check a setting. Select the iPod in iTunes (click its device button on horizontal bar) to show its Summary setting screen in iTunes window. Find the checkbox for Manually manage music [and videos]. If it is not checked already, checkmark it, and click Apply. (Your iPod is likely to be set this way already.)
Then, show your music library in iTunes (click the Music button at left end of horizontal bar). Near middle of horizontal bar, click Playlists. A sidebar appears along left side of window, with your iPod listed under Devices. At right end of horizontal bar, use the control to choose the view of your music library. I like using the Songs view, to show a plain sortable song list with columns. But if the new songs are from the same album or artist, you can use the Albums or Artists view.
From the song list, click-hold-drag a song you want to the sidebar, and drop it on the iPod. You can do this with more than one song selected at the same time. Or you can drag and drop a set of songs from an album. Whatever you drag and drop on the iPod are loaded. Alternately, instead of dragging/dropping, right-click a song, item, or selection and Add to Playlist -> [Name of iPod].
Here's how to move songs from the iPod manually. In the sidebar, click the small triangle to the left of the iPod. The iPod's content list drops down, indented below the iPod. Click Music on the content list. To the right, iPod's song list is shown. To remove a song from the iPod, select it on the list and press Delete on keyboard. You can do this with more than one song selected.
Please post back if you want to learn how to set up automatic syncing. Depending on how you use your iPod, and size of your iTunes library, automatic syncing can be more convenient.