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I have altered my iTunes playlist on my PC because I had to get a new computer due to some hacker putting a crypto lock on my hard drive. I never used the iCloud to back up my playlist and thought that I was backing up my playlist properly on an external hard drive. Turns out that I never backed up my playlist properly. I lost everything! So, I painstakingly loaded all of my CDs into my playlist on my PC. I also went through the trouble of eliminating duplicate songs, which I had never done before. I still have my previous playlist on my iPhone and iPod. Since I am so ignorant when it comes to this stuff, I didn't know if I could have backed up either my iPhone or iPod to the PC playlist instead of importing all of my CDs again to the PC playlist. So, I went through the agony of importing the CDs. I actually have no knowledge on how iTunes playlists work. Now that I went through the trouble of importing all of my CDs again and eliminated the duplicate songs.

  1. if I plug my iPhone into the tower and sync and backup my iPhone, will the syncing replace my new PC playlist with my iPhone playlist?
  2. And, will the syncing also put songs and albums that are on my iPhone, but not on my PC playlist, from my iPhone to my PC playlist.
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Your iOS device only syncs with 1 computer, if you gonna sync on a new computer, your music on your iOS device will be replaced with what's in your iTunes Library on computer.

You can't sync FROM your iOS device to computer, because of copyright reasons, eg. I buy music and sync them for all my friends' computers. That's a no-no! :P

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I would say, you can simplify things greatly by just focusing on the PC for a bit.

The process to back up and restore your iTunes library is at https://support.apple.com/en-us/HT201625

You can optionally back up all the playlist information (which can be used to import a playlist, but doesn't save the files themselves) if you make a hot new playlist mix that you don't want to lose but you don't have lots of new content in the library.

Once you have your PC set - you can decide if you want to keep your backups local or if you can use iTunes Match or Apple Music to back things up to Apple's cloud.

When that is clear - you can look at each iOS device to transfer any content back to the library. Unless you use a subscription Match/Music - playlists created on the iOS device don't sync back unless you have automatic syncing enabled in my experience. There are thirt party tools to help with this too, but the Apple/iTunes only solution is to do the work on iTunes and push/sync it to the iOS devices. One way transmission.

  1. Quite possibly - the new iTunes library wants to wipe the old iOS info and start over.
  2. No - you want to disable syncing and then "transfer" songs back. You will need to write down the playlists on paper and re-implement them when they get cleared in the next sync.

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