Copying All Your Music to Your iPhone
You would think this would be easy, copying my entire library, since all my music is on my Mac, and thus a simple USB cable would be all I'd need to copy all that music over to my new phone. If you think this is true, you clearly haven’t been reading my blog for very long. For several years now, as Apple has ignored users in my situation, the process of getting my songs onto my phone has resulted in doubled tracks, missing tracks, incorrect album artwork, songs that simply never copy, songs that appear to be on the phone but refuse to play, and on and on. It has been a nightmare for a geek like me who makes an effort to have a very orderly library and who likes to listen to entire albums.
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When you restore from a backup during the setup process, your iPhone will not only restore all your settings and apps; it will also start downloading music. Not all your music. Just whatever songs were on your previous phone that happened to be purchased in the iTunes Music Store. This will likely leave you with a weird mix of some tracks from your entire library. If you have iTunes Match or Apple Music, the restore may also attempt to grab your other tracks, but I’ve found this completely unreliable.
Basically, you have no idea what you’ll actually get from a restore, so it’s best to remove everything and start over from scratch.
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There are lots of ways to copy your songs over, but in my experience there’s only one way that works reliably. (At least it does now. This would not have been true in earlier versions of iTunes.) For me, all the auto-syncing methods are unreliable. I tried again this year, resulting in multiple issues. What works best for me, thanks to that most recent iTunes update, is good old-fashioned drag and drop.
Update (2017-12-11): Joe Cieplinski:
You read that right. Moving forward, whenever I get a new audio track that isn’t from Apple Music, I’ll have to add the track to iTunes, turn on iCloud Music Library on the Mac, let it upload that new track to the cloud and download all these thousands of duplicates, then turn off iCloud Music Library on the Mac to remove all the duplicates.
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My use case is similar to Joe Cieplinski's use case, with quite a few CDs loaded into iTunes over the years. As a result, for reliability reasons, I've simply given up on using my iPhone as my main music player. I bought a classic iPod with a 160 GB drive, and that is the music player I take wherever I go. It just works, while, as Joe says, the iPhone's behavior can be difficult to predict. I'll download and listen to music once in a while, when I don't have my iPod for whatever reason, but I make no assumptions about the music that is on the iPhone, and I don't count on it. I don't know what I'll do when the day comes that Apple tells me I can't use my iPod any more.
