oof   

Hmm, error 14. Not familiar with it. Is this version of iTunes the one from the Microsoft Store? Any particular reason you're using iTunes to perform the update? 

Restore failed as well. Trying on another computer. @DrMacintosh any suggestions? 

Does the phone work or did it bork itself? 

Nope. It had it plugged in to transfer some songs over and figured I might as well get the update done. 

Is there something wrong with the iPhone? Or are you just trying to update to iOS 13?

If the phone works, I suggest updating OTA. Windows iTunes has issues. 

@DrMacintosh Restore completed on the other computer. And uh what the hell... I was restoring from my iCloud backup and it says "This iCloud backup includes purchases from the iTunes Store that were made with a different Apple ID. Is this because the device was a CPO device? 

@TopHatProductions115 just updating to iOS 13. Just got the device last week certified pre-owned from my carrier (sketchy eh?).

Do you by any chance have an pirated Music? iTunes tracks are not DRM protected, but iTunes does know which account purchased the song. If the account that purchased the song does not match your account, you can see that error. However you can simply manually sync the tracks with iTunes and you should be able to get rid of that error. 

I think we all know the answer to that then  It was set to manually manage when I set it up last week. My old iPhone 4 was synced to an iTunes profile so maybe that’s it?

Oh - so the seller didn't wipe it before giving it to you? Just checking...

@TopHatProductions115 The device was wiped by the OEM who did the reconditioning and sold to me from my carrier (Fido). It didn’t ask me for the previous Apple ID used. Setup was just like for a brand new device.