iPod Can't do a backup or add files to old iPOD

[Perene]

I have here with me the 80 GB iPOD Classic, 5th generation, from 2006. It has 741 files (2 GB). I need to do a backup of those files to my PC, and at the same time add new songs (MP3) I have here.

However neither of those things are working with iTunes ver. 12.6.5.3, in Windows 10-64 bit. When I click on "Sync" nothing happens, and when I visit "Sync songs" (there's an option called "complete library" below) it warns me "are you sure you want to REMOVE the existing contents from this iPOD and sync with the iTunes library"?

I believe when I asked iTunes to add more files the iTunes did, but at the same time it can't do that without removing the existing files.

Any idea how I may save the existing files and add more? I think I am missing something.

 

[Perene]

OK, here's the thing:

I solved this problem, but not with iTunes.

As I said before clicking in "Sync musics" will probably delete the current data stored in this device. So I got this software for Windows (which is paid, BTW):

https://www.syncios.com/

And was able to EXPORT all the songs in this iPOD. Then I restored to factory settings. After that I used iTunes again and was able to finally "add files to library" and use the "Sync songs" option, and then click on "Synchronize" to upload the files from my PC to the iPOD.

As a result all files are there: the ones the iPOD had and the new songs I am adding today.

If there's another way to do this without the help of a specific software please let me know.