Nano 1G Plays Wrong Books? (Again)

It's possible there is data corruption in the nano's storage. You may want to do a Restore on the nano, from the nano's Summary tab in iTunes. This will erase the nano, re-install its software, and set it to default settings. You can then re-sync your content. If there's a problem related to data corruption or a software glitch, a Restore should fix it.

If you manage content manually, it will be somewhat more tedious to reload your nano after the Restore. Also, if there is content on the nano that is not in your current iTunes library, you will need to "off-load" such files (if you want to keep them) from the nano (onto your computer), before the Restore process erases it off the nano.

If you set up automatic syncing by using the nano's "tabs" in iTunes (the row that starts with Summary when you select the nano in the iTunes sidebar), recovering from a Restore is fairly easy. For example, you could have a playlist in iTunes with all the songs you want on the nano, that you keep regularly updated with adding new songs (and removing old songs). After the Restore, you just need to select that playlist again on the nano's Music tab, and sync. You can do the same with Podcasts and other content types.

Using the manual method, you will need to manually add content back onto the nano. There is no record kept of what is loaded on an iPod manually.

That's disappointing. You said it worked fine for a long time, before this problem occurred. And now, not even doing a Restore, which should put it back to the original state and settings, will fix the problem. Therefore, the cause may be something in your iTunes Library database file that, for some reason, only affects this iPod model.

You said earlier that you manually manage content on the nano. Have you ever tried to use the automatic sync settings to load your books? To do this select the iPod in iTunes. There is a row of "tabs" (buttons) that starts with Summary. Click on the Books tab, and check the box for Sync Audiobooks. Below that choose Selected audiobooks, and select a small number of audiobook to sync as a test.

NOTE: If you set an iTunes media category, such as Music or Books to sync automatically, you will not be using the manual loading method anymore. Whatever is currently on the iPod will be replaced by your selection on those tabs. Since you just did a Restore, that may not be a concern.

Click the Apply button to sync the selected audiobooks to the nano. See if the problem recurs if automatic syncing is used to load the audiobooks.

I don't use audiobook very much, but you should be able to select individual parts of multi-part books (which may be what you called a "stack"). On the iPod's Books tab, check Sync Audiobooks, choose Selected audiobooks, and select the desired audiobooks on the left-side list below. Highlight one of the books on the list to the left, and the "parts" of that book are shown on the list to the right. For books that have more than one part, checkmark only the part(s) you want to load.

Alternately, using automatic syncing may be easier (more familiar) for you if you use playlists. Create a new regular playlist in iTunes and call it something like "iPod Books." In iTunes, manually drag the audiobooks you want on the iPod to that playlist (not to the iPod). On the iPod's Books tab, select that one playlist from the list under Include Audiobooks from Playlists. That's all you need to select on the Books tab. In this way, instead of manually updating the iPod with books, you are manually updating a playlist with books, then automatically syncing that playlist to the iPod. You can use the same playlist method on the Music tab; create and manually maintain a playlist of songs for the iPod ("iPod Songs"), and select that one playlist on the Music tab to automatically sync to the iPod.

I find automatic syncing much more convenient, because I don't need to have the iPod connected when I update those playlists. But when I connect the iPod, it "automatically" syncs with my "manual" changes (since the last sync), all at once. In this case, I'm not advocating that you use this method all the time, but that you try it to see if it makes a difference for this problem you have. If it does make a difference, it may help to determine the cause.

You can use the same playlist approach with podcasts. You can add and remove individual podcast episodes to a playlist and select that one playlist for syncing on the iPod's Podcasts tab.

Conceptually, instead of manually updaing the iPod directly (like you do now), you are updating the playlists. Your actions are basically the same, except you are dragging stuff to a playlist instead of the iPod. When you sync, all of your changes to the playlist(s) since the last sync are made to the iPod.

One advantage of syncing playlists automatically is that your iPod can be disconnected when you make updates (add and remove items). You can make all of your changes very quickly to the playlists; adding items directly to the iPod takes a bit of time per item. The next time you connect the iPod, it syncs any changes automatically, all at once.

Another advantage is easy recovery. If you do a Restore, or if you get that "new" iPod, you don't have to manually load the iPod to recreate what you had before. Just select the same playlist(s) on the new (or restored) iPod's Music, Books, and/or Podcasts tabs, and sync. Everything will be like it was before, in just a few minutes.

And in this case, it may actually make a difference. When you manually update the iPod, the items are added or removed one (or several) items at a time. When it is done automatically, iTunes uses a different process to make ALL of the changes at once. So, if the process is what is failing (possibly due to an odd bug), it may work properly after an automatic sync. That's why you should give it a try (as a test), even if you don't want to use automatic syncing regularly.

I just want to say THANKS to both of you ... I've been having the same problem with my iPod Nano and have saved this conversation to try all the solutions. Very nice to have found this already answered!