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Music Transfer to iPad2


iPF Noob
Jul 23, 2017
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Hi all, I have a major mess that I need help with. I'll explain the mess below.

The Mess:
OK, I have a friend who has 2 older Mac laptops and one iPad, the laptops are a "used to be white" A1181 and a later silver version MacBook that I will find the version for later, the iPad I am assuming is an iPad2 due to the iOS being 9.3.5 and cannot be further updated, but again I will check later and add the model version here.

The Problem/s:
The guy is a musician and used to use the A1181 laptop to create playlists in iTunes and an App called Backing Trax that he used to be able to play his sessions, it would play one track and then pause until he wanted to play the next track. For ease of use (enter irony) he decided he wanted to use an iPad that his daughter gifted him.

The issue is transferring music to the iPad from the A1181, sounds simple doesn't it...

The A1181 has OS X 10.6.8 which I believe is the last/latest version of Snow Leopard. iTunes and the iPad are not playing ball and a message keeps asking to update iTunes but the A1181 will not update any more.

The Silver MacBook; which was showing the same update iTunes message as the A1181, now has El Capitan and now accepts the iPad.

The problem now is that all of the music that is required to do his gigs is on the A1181 and needs to be on the Silver MacBook, sounds fairly simple doesn't it...

Things tried so far.
  • Created a time Machine backup of the A1181 laptop
  • Copied the iTunes folders from the A1181 and the Silver MacBook, I will call these iTunes-A1181 and iTunes-Silver respectfully.
  • Selected all of the music folders from iTunes-A1181 (now on my external HDD) and dragged and dropped them into the open iTunes app on the Silver MacBook, iTunes accepted them all and in total copied 606 songs.
  • He connected the iPad to the Silver MacBook and decided to let it sync, "wrong choice" it removed loads of music from the iPad and from iTunes. (Fortunately I had backups of the iTunes folder) :rolleyes: so got back the music that was originally there.
I have explained to him he has one hell of a mess and that in general, iTunes will remove anything from the iPad that is not in iTunes, well that’s my assumption anyway. I have told him he needs to have backups of all the music and then to start fresh from the iPad and reset it and then put his Apple ID on it.

If new hardware isn't forth coming, I told him to focus on the Silver MacBook and iPad and forget the A1181.

So if anyone has any thoughts on this debacle, please share them

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