"MY" Music

Long story, but I’m kinda old school… way back in the day, I got a LOT of CDs, ripped them all into my digital library (about 75G worth!). My cMP desktop is stuck at High Sierra what with what Cupertino refusing to even allow nVidia drivers (and I have an big investment in such a GPU, which, btw, works fabulously for my gaming needs running win10). My modern day investment (considerable) is in the 12.9" iPad Pro (oh, that screen!). Have NO interest in any monthly charge music services no matter from where. Simple, take a big chunk of the library I already own and get it rolling on my iPad.

I figure I should be able to figure this out… BUT I can not. It seems everything, but everything in the iOS Music app is 100% tied into their paid music service. There’s even a ton of songs in it’s “library” which has to mean at their music service.

Am I totally out of luck? 2 issues, how can I copy, say 30-40G of my music to the tablet and what/how can I play FROM that collection? A potential third question involves all the meta data I have tied up in my iTunes library on the desktop, but that is honestly less of a concern.

If you want to manually sync your Mac library to your iPad, see here. You can do it via USB and set up doing it in the future via WiFi. Apple also has a $25/year Cloud service called iTunes Match that will scan your library and either give you access to each tune from Apple Music or, if it can’t find it, upload yours. This allows having all your music available on your mobile device without storing it all there. See here.

There are 3rd party explanations for these processes. Just search in your favorite search engine for ‘sync mac music to ipad’ and ‘iTunes Match’ .


All good advice from @aforkosh
The one caveat with iTunes Match

is that there is a limit to the number of tracks you can put in the cloud. 100,000 I believe without re-checking. So in my similar-to-you case of a large library ripped from CDs I own, I had to create a second iTunes library that has less tracks. Other than that, iTunes Match works pretty well once it is all uploaded/matched. The tracks that match are matched at 256kbps, which depending on the state of your iTunes library, may or may not be an upgrade. For me, many tracks had been ripped at lower kbps, so the $25/yr is money well spent.


@aforkosh has the right answer with his link. But do take notice in that page that…

If you use iCloud or other services like Apple Music to keep your content up-to-date across all of your devices, some syncing features through iTunes might be turned off.

Could that be the problem?

I routinely sync music to my iPhone SE (2016) and iPad Mini 5 using both iTunes on Sierra or on Mojave on my cMP.

With regards to how to play from your collection without using Apple’s Music app, there are a number of third-party music players that can play from your on-device collection. My personal choice right now is jetAudio, which recognizes iTunes playlists that have been synced via iTunes or Finder (they have to be synced as playlists, of course), and also supports creating its own playlists. It’s compatible with CarPlay (big plus to me) and has several optional add-ons for tweaking your audio (equalizers and such).

My only disappointment with jetAudio is that is doesn’t have the option to shuffle playlists by album instead of by track. Minor gripe, to be sure, but it’s a feature I use a lot in iTunes/Music on my Mac, and I have several playlists that are set up specifically to be shuffled by album.

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Two possibilities:

  1. If your music is in iTunes/Music on macOS, you can sync its library with your iPad (via USB or Wi-Fi). If you don’t want to copy everything, you can sync selected playlists (best way) or manually manage music on the device (worse).

  2. You can enable Home Sharing on the Mac. If you are using iTunes, enable it there. If you are on a later macOS running Music, enable it via Media sharing in the system preferences. Then devices on the same LAN can see and stream your media library.

    If you do this via iTunes, then iTunes must be running for the sharing to work. If you do it via Media Sharing, then it should work all the time.

I think option 1 (sync music to the device) is the best solution, because you will be able to transport the music with you and not only listen do it when you’re on the same LAN as your Mac, but the music will consume storage space on the iPad, which you may not want to give up.

I intensely hate all of Apple’s music apps since iTunes began to decide for me what I wanted and how I wanted it, and especially when it began to mess up CDs I loaded directly onto the app. I have iTunes Match but again, when I want to use the music it will not obey my requests. Soooo, I no longer buy music through Apple, use my own devices to get my tracks properly copied on the Mac, then use WALTR PRO app to load them into the Music app on my iOS devices. Since Apple has not touched those files I no longer discover that the app has messed things up by linking it to iTunes Match. Still looking for a nice independent app for iOS that gets me out of Apple.

One thing I would like is a timer in that app that would allow me to listen to some of my many Old Time Radio programs and have them shut off after 30-60 minutes as I go to sleep lol.

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It’s not in the Music app itself, but in the Timer pane of the iOS Clock app, one of the options for “When Timer Ends” is “Stop Playing”. That’s what I normally use to play music to go to sleep.



huh, another thing I never noticed! Amazing the number of hidden/unpublicized features in iOS…


I remember reading about iTunes Match creating problems like this almost from the day it was first introduced.

FWIW, I have a fairly large music collection (about 15,000 tracks, mostly ripped from CDs, some purchased from the iTunes store or downloaded from Amazon). I have never used Apple Music or iTunes Match, I only sync my devices over USB, and I have never encountered problems like these.


@dave6 thank you for that great tip! I used it last night and slept like a baby - thanks to Jack Benny :wink:

@Shamino I really regret ever having gone to iTunes Match but I had/have so many tracks trapped in my purchases, too many locked up because they are part of the old protection formats.

Thanks everyone, good info in here. Not sure why, but I used to have iTunes “see” my mobile devices, but somehow that seemed to end within the as year. Tried plugging one of them, in, got the “need software update” which I believe does not force me to do any OS install beyond HS (it HAS to stay there due to a GTX980 GPU that performs very, very well).

Yes I remember hearing about all sorts of issues with the “Match” program, plus it costs and I have heard seen no mention of it from Cupertino in decades so surprised they MAY still support it. All the hundreds of playlists I have are solely artist based, so I’ll just sync maybe 30G worth with the option I can delete some and add other as I see fit.

Ugh, for some reason all my “smart” playlists got changed from Music to Podcasts! Looks like I have some work ahead of me…

If you’re syncing your music files with iTunes, but don’t like the iOS Music app, the third-party Cs Music Player is a great option. It works with the system’s music library but doesn’t try to push subscriptions or recommendations in your face. @dougeddy, this might help with your issues with Apple’s Music app, too.

Thank you for the suggestion. I just purchased it and downloaded it. At first glance not sure if it is an improvement on Music - saw one of my albums that was iTunes messed up despite the fact of the album was one that I imported directly from an Amazon purchase and I had used Fission (a fantastic app) to change info in a way that would separate it from the iTunes version which was an import from my own CD. Will work with it to get used to it and really appreciate your input on it.

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If you ultimately find you can’t get it to work for you, you should be able to ask for a refund from the App Store. Hopefully it can work for you though!

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Paul, I too am stuck at High Sierra on my iMac but I have all my music on my iPhone 10 (iOS 14.4.2), my iPad Mini 5 (iOS 14.4.2), and on my “iPod 3GS” (iOS 6.1.6). I just continue to sync with iTunes I can’t go past iOS 14.4.2 because of one critical app that I use. If I go past iOS 14.4.2, I’ll lose access to that app. Anyway I just connect my iDevices to my iMac via an USB cable to sync. My iTunes settings are:

Summary Page Options Section: All unchecked
Music Page: “Sync Music” checked and then “Entire music library” radio button is selected.

The last version of iTunes that runs on MacOS 10.13.6 is apparently 12.8.2 but I don’t know if it will work with iOS versions 6.1.6 and 14.4.2. Oh, when I connect my iDevices to iTunes, I get a message I have to install a software update to connect. However, because I have never been able to find exactly what the update is or does, I just click the “Ignore” button and don’t have any problem connecting the iDevice.

Oh, if you don’t want to (or can’t) use iTunes, I suggest checking out iMazing 2 from DigiDNA.

Retroactive modifies several older Mac programs including iTunes, Aperture, and iPhoto to run on macOS releases through Monterey. Most features run fine, but some do not work. See the Read Me associated with the app for more information.

I have not used it for iTunes but did use it to create a version of Aperture that ran under BigSur and now runs under Monterey.

I consider it a Band-Aid, and, eventually, the programs it patches will become non-functional, but it may enable you to upgrade macOS to a later release while still running the programs you consider essential.

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I mentioned Retroactive a few weeks ago in this thread for those who don’t want or can’t use the Music app:

One user was able to install iTunes 12.9.5 under Big Sur. His post is near the end of the thread. I still use iTunes 10.7 CoverFlow on Catalina due to Retroactive so it is a very useful app.

Has anyone else found a way to handle this? The old non-iOS iPods had a “Shuffle, grouped by album” mode, but that was removed from iOS devices, and it drives me crazy - much of my collection is Classical, and playing randomly-selected movements is a terrible way to do a random walk through your collection. I’ve tried Adrian Schönig’s Longplay app, which writeups led me to believe could play albums at random, but in fact merely gives you an assortment of ways to select individual albums from your Library. I’d really prefer to Shuffle a playlist, an artist, a genre, or my entire library and have it play randomly selected albums, one after another.

That’s always been a concern of mine, given that I have a Library of 1,300+ CDs hand-ripped to my Mac server, but a quick bootup of iTunes shows that only amounts to 22,275 tracks, so I’m still less than a quarter way to that limit. Having a lot of classical recordings probably helps there, as the average number of tracks per CD tends toward eight (i.e., 2 four-movement works).

The initial problems with iTunes Match deleting people’s libraries or misidentifying albums leading to it substituting the wrong music has kept me from ever trying it. I’m still syncing my whole library via USB to an iPod Touch, giving me my entire library wherever I go, regardless of whether I have an internet connection. Prior to Apple’s releasing a 256 iPod Touch I was doing that with an iPod Classic, and once I switched over I really missed the ability to shuffle by album.

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Take a long look a Plex, it may solve all your problems:

Plex can manage your music library and stream it to all your devices. A subscription which goes to funding Plex software development is required to download an offline copy of your music to your mobile devices among many other benefits. There is a lifetime pass option. Plex Media Server will run on Mac OS Mavericks and above as well as Windows and Linux. There’s a metric ton of clients. Plex can handle all your media from TV / Movies / Music / Podcasts / Photos / personal videos, etc. You’ll want the Plex Amp app for music. You can stream to Sonos speakers and it works remarkably well.

I recommend trying it out as it’s free to use with most functionality intact without a Plex Pass subscription.