Syncing music from a Mac to a Windows Phone / Windows 10 Mobile it's a lot easier than you think.
Apple like you to have the latest kit, pushing older tech out and forcing obsoletion of perfectly good hardware via software cut offs. It's not an exclusively Apple tactic but they are more aggressive at it.
To cut a long story short, my dad's 2008 white MacBook running Mac OSX 10.7 'Lion' won't sync with his iPhone 5 because it is running iOS10. However he was both delighted and disgusted to know his spare Microsoft Lumia 550 running Windows 10 Mobile would.
For the purpose of this article I will use the term Windows Phone to cover Windows Mobile 10 too.
As an iPhone user he uses iTunes to put music onto his Mac and then sync to his iPhone. The process to get that onto a Windows Phone handset uses your existing iTunes library, so the leg work was already there.
I grabbed my copy of the Windows Phone app – which unfortunately Microsoft took down about a year ago – and copied it to his Mac.
On running it for the first time you have to tell your Mac to use the connected Windows Phone and similar to iTunes tell it whether you want to sync the entire library or just selected playlists. Then you sit back and watch the magic happen.
The Windows Phone app has a very similar look to iTunes – which is good for someone who isn't too familiar with new apps.
The first sync takes a while as it is pulling everything from your playlist onto a fresh phone, but a progress bar shows you what it is doing.
After that you simply use iTunes as you would before, ripping or downloading music and placing it into the playlist or playlists you want synced. Then connect your Windows Phone, run the Windows Phone app and sit back and let it do its thing. It will sync the playlist, adding the new music and taking off any you may have removed from the playlist too.
No user intervention is required.
It isn't all plain sailing. The first caveat of this excellent work around is that Microsoft have taken down the app and not replaced it with anything, but it can be found. The second, is that you need to grab the right version and tweak it depending on your OSX/macOS version.
El Capitan and Sierra broke the existing app but an easy fix to get it working is available. Check out the following articles for fixes.
El Capitan Windows Phone App Fix
Windows Phone App Fix for macOS Sierra
I haven't had the opportunity to see if this is once again broken with the release of High Sierra.
My dad was amazed at how easy it was to get music on his Microsoft handset, a phone available for under £40 used, something his shiny Apple device was being hindered from doing by Apple themselves.
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Source: Your Aging Mac Can Sync Music To A Windows Phone… Even If Your iPhone Can't
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