this post was submitted on 22 Jun 2025
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I was using iTunes 12.9.5 thru Retroactive but then the install crapped itself, still not sure what the issue was. Ended up digging out a 2012 Mac Mini and doing a clean install of Mavericks with iTunes 11.3.1. If anyone else is having issues syncing a 3rd gen, try putting it in disk mode then connecting it, fixed the freezing issue when syncing for me.