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ITunes syncing

Joined
Oct 18, 2009
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South Carolina
Your Mac's Specs
2015 iMac running Mojave 10.14. 1TB Drive, 8 gigs RAM.
Having updated to Catalina, syncing does not seem to be as easy as it once was. I have about 2000 songs in my iTunes library. They are from multiple sources, including CDs, on versions from vinyl to MP3, purchases thru the music app, and downloads from sites such Frostwire. They work perfectly on my iMac and recently on my iPhone and IPad.

Recently, I was trying to update the library to my iPhone and must have done something wrong, because the library and phone were reduced to about 40 songs. Panic time. I restored the library on the iMac from Time Machine and then tried syncing again to the phone. It worked...partially. There were some songs that did not sync as well as some albums.

Is it something I’m doing or is it the fault of constantly upgrading to these new OS systems? Apple used to be so easy to use. Acting more like Windows all the time.

Thanks for any help.
 
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Apr 18, 2020
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I am sorry I can't answer the syncing question but have you thought about a separate backup? I save all my films and music 'off Apple' just for peace of mind. I even use the ancient Macbook White I own right now running OS Sierra because with any later operating system my third party software for ripping films out of iTunes for personal use doesn't work. Apple is great, really I bought into the whole ecosystem, but do you really want to rely on the cloud with SSD real estate being so cheap? Totally independent of apple and the Internet my kids can watch any film they want from our collection of over 300 films and our substantial music collection is also preserved.
 
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