TS1363 My iPhone 5S will backup to both my PC and cloud, it says it's synching, but new music I've put in to iTunes doesn't transfer over. I ran diagnostics and it says it doesn't see the device. Never had a problem before...

My iPhone 5s will backup to both my PC and cloud, it then says it's syncing, but new music that I put in to iTunes doesn't transfer over to the phone.

It depends on the iPod shuffle model...  Assuming your shuffle is the 4th gen (or 3rd gen) model, do you use automatic syncing or the manual method (drag and drop song on iPod in iTunes)?
This document shows the four shuffle models, and provides general info about loading content on shuffles
http://support.apple.com/kb/ht1719

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