Getting a used purchased 160 GB iPod loaded with my music on Windows 10

DaveFHarr wrote:

After a short while I get an error message that "The iPod could not be restored. An unknown error occurred (1439)".

In the event of that type of error, see this Apple article: If you see an error when you update or restore your iPhone, iPad, or iPod - Apple Support.

One of the tips in it is to ensure that you have the latest version of iTunes on your machine. On this point, can you confirm which version number you have (not simply that it's the "latest version")? Look on iTunes' Help menu for the About iTunes. It may hold the key to the issue.

DaveFHarr wrote:

Also, somewhere along the way I saw that I should tic the "Enable Disc use" button which I did and have left that way. Is this correct?

No.

So I tried to sync again and it actually worked for awhile before various error messages started appearing.

What are the messages? You don't need to list them all at this time, but one or two might help. Is one of the messages telling you that so,me songs could not be synced because the original file could not be found?

I don't know your level of experience with iTunes, but the following steps show you how it should be done, either the first time or if making significant changes to the setup (not specifically to what music is added).

• when the iPod is seen by iTunes, tap on the iPod icon at the top, just below the menu bar:

This will display the Device/Settings/Summary pane. Switch to Device/Settings/Music pane (1.) as shown in the screenshot below:

• make sure that the Sync Music button (2.) is ticked (checked)
• for step 3., choose either:
  • Entire music library - which will attempt to add all of your library's content
  • Selected playlists, artists, albums and genres - which will then display section 4. from which you can choose which items (albums, playlists etc.) to add to the iPod
  • tap the Sync (or Apply) button in the lower right corner of the iTunes window (not shown in the screenshot)

That's it.

One more thing. It sounds to me as though you have an iPod Classic, which has a mechanical hard drive in it. These drives can fail, so it is possible that you hard drive is beginning to fail and some sections of the drive cannot have anything written to it.

I'm not an expert regarding those figures, but they don't seem too bad to me.

Let's look at just a couple of things for now.

The message saying that the original file cannot be found happens when iTunes can no longer find the file for a song that is listed in its library. That in turn can occur when the file itself has been moved, renamed or deleted (either by you in Windows Explorer or by third-party software) after it was added to your library.

DaveFHarr wrote:

I ticked the entire music library because I saw no way to tick groups of, for example, artists while skipping over a few. Individually selecting each arist, playlist, etc would take me all day.

If your entire library will fit onto the iPod, then there's specific reason to choose the "selected playlists" option. It's useful when your library has more music than can be fitted into the iPod. That's why I use the selected playlists option. I referred to it to give you a better understanding of what the options that you could see in the screenshot mean.

I'm not real experienced with syncing iPods. I've done it a couple of times successfully but this is one I purchased from eBay fully loaded.

If you've done it once, then it stands to reason that you can do it again. The procedure I explained in a previous post is to setup Sync options. Now that you've completed that, there's no reason to do it again unless you wish to change the way the iPod is synchronised. If you add more music to your library, simply connect the iPod to your iTunes Library and let a Sync take place. That will add the new music.

Regarding the music that was on the iPod when you bought it: it was the seller's responsibility to remove all the existing content before sending it to you. Specifically, the seller had no legal right to leave the music on there for someone else's benefit. Since the music was still on there when you received it, all you needed to do was use Sync to remove it. If there was music on it that you liked, you could buy your own copy. (When I visited an Apple Store to look at iPods, the in-store iPod demonstration iPods all had a piece of music on them that I liked. I made a note of the track name and artist and bought a copy of that track as soon as I could.)

I think the first issue to start trying to resolve is any track in your iTunes Library that was marked at Sync time as "cannot be found". Those tracks probably now have an exclamation mark next to the track title and cannot be played:

• • the first question to ask yourself is did you move, rename or delete files for any of the "cannot be found" tracks listed in your library? As a part of this question, did you rename or delete any path to the file (i.e. a folder name)? If so, try to restore what you changed back to its original
  • to find the correct location for a missing file:
    • right-click the entry in your library and choose Song Info from the pop-up menu
    • in the message box that appears, choose the No option:

• • • the Song Info panel will open onto the Details tab. Switch to the File tab (2.):

• • • note the location information(3.) at the bottom of the panel. It shows the filepath that iTunes is looking in and - after the last / separator, the filename. In the screenshot above, the filename (which is almost the same as the track name) is 03 Tom's Diner (A Cappella).m4a
    • go to the folder shown in that path (in this case, drill down into the the Compilations folder and look for the Tom's Diner (Single) folder):

• • • notice the leading x in the filename. However, iTunes is looking for a file that does not begin with the letter x. In this case, I renamed the file to remove that leading x and then returned to iTunes and tried to play the song. It played and that issue (for that track) was resolved

If your iTunes was downloaded from Apple (as opposed to the Microsoft Store*), then there should be a Check for Updates option, but note that it's a separate line on the Help menu. It is not in the Help/About iTunes option:

Your version, 12.13.1.3, is the latest version on the day of writing this. Here's a screenshot from the Help/Check for Updates option in my iTunes this morning:

The Check for new software updates automatically (in Edit/Preferences) will simply let you know that there is an update. You still have to download it and by doing so from the prompt, the installation will be done for you.

One tip I can offer at this time is to try the suggested methods again. Sometimes, it can take a couple of tries to get iTunes to fix an iPod. In the meantime, turingtest2 is still active here. If he spots your comments, perhaps he might add to the discussion.

* The Microsoft Store version of iTunes updates fully automatically and as far as I know, silently. The user needs to do nothing.

You don't need to do anything specific about the music that's currently on the iPod.

If you set your iTunes to Sync (synchronise) with the iPod, you will see a message telling you that the existing media will be erased from the iPod and replaced by the media in your library. You do need to tell your iTunes what you want to add to the iPod. To do that, look on the Device/Settings/Music tab (that appears in iTunes once it sees the iPod) and select the button that says Sync Music. The default is that iTunes will add all the music in your library.

The existing content on the iPod is not preventing you from adding your music, you simply need to let iTunes erase the old content, which it will do when you let it use Sync.

Just so you know, the F01, F02 (etc.) folders that you see when using Windows Explorers is normal, they are the folders containing the music in encrypted form that prevents the music being copied back from the iPod. Also, you cannot use Windows Explorer to manage the iPod.

You're welcome.

try to erase it with windows then try to restore it on your main mac