How do I transfer music from an old iPod to a new iPhone using iTunes?

SchottyCallen:

I sense that you're not getting anywhere with this problem, so perhaps a different approach is needed, partly to ensure that nothing obvious has been missed, but also in an attempt to resolve the issue.

Let's go back to the beginning: how did you add the music to your iPod originally?

• • if you added all the music on your iPod by buying all of it directly from the iTunes Store (on the iPod), then you now sign into the same Apple account on the iPhone and download your previous purchases from the store directly to the phone. Alternatively, you can sign into your Apple account in iTunes (the programme on your computer) and download the purchases from the store to iTunes. Then add the music from iTunes to your phone
  • if you added music to your iPod that came from other sources (either in addition, or not, to using the iTunes Store), such as:
    • copies of CDs, those copies will be in your iTunes Library, on your computer (as you would have used iTunes to add them to your iPod)
    • digital purchases from Amazon, Bandcamp etc., you would have downloaded those purchases to your computer and added them to your iTunes Library, then once again, used iTunes to add them to your iPod

Therefore, if you have a mix of music, purchased from the iTunes Store as well as other sources (CDs, online stores), it should all be in your iTunes Library as you would have used iTunes to add it to your iPod, so once again, use iTunes to copy that music to your iPhone.

If you no longer have access to your iTunes Library and no back up of it either, your options are to use the suggestions mentioned by Phil0124 and turingtest2 to recover everything from the iPod, or rebuild your library in iTunes and copy that rebuilt library to the phone.

Rebuilding your library:

• • music from the iTunes Store - download purchases from your account to iTunes
  • music from other online sources - go to your account with that store and re-download your past purchases
  • music from CDs - re-copy the CD into iTunes. If you no longer have the CD, you will need to decide how you wish to proceed. You could re-purchase digital copies from an online store (iTunes Store or Amazon etc.), or if you don't think it's worth it to you to spend that money, go without that music

If you do have to rebuild your library, you will of course lose any playlists and song ratings that you made on your iPod.