iTunes playlists won't sync between both of my Macs

Hey Community, I'm in desperate need of help. I have been to two apple stores, then when they couldnt help they referred me to itunes specialist on the phone. Apple worked with me for about a week and then said they were sending my data to their computer team with videos i took of my screen. I never heard back from them. I will go into detail the best I can. Itunes is my world, and part of my business. I have worked on my playlists since I was 13 and have my whole life there. When they switched from itunes to music a lot happened and it has been a crazy adjustment. Apple was able to save my playlists at least which is imperative to me. I have always had my music and library saved onto an external hard drive. I have recently switched that to a SSD drive for more safety. I have always had two computers and had my itunes on both reading the same playlists. So i recently purchased a new M2 macbook air and a new Mac Studio as my at home desktop. It is very important that my itunes talks to both computers and whatever i do on one computer saves on the other. I have both 7,000 songs purchased from apple and over 30,000 songs copied on my itunes over time from cds etc. I purchased the laptop first for a few months and everything switched over fine. Once I purchased the mac studio I brought both to the apple store so they could help me set up itunes on both. For the first few days it was working great and whatever i did on both computers was saved to one another. After a few days I noticed it wasnt saving,  thats when I brought my computers back to apple twice and then talked to apple on the phone for a week. Obviously we made sure the same library was chosen for both, and made sure both computers were taking the songs out of the same folder. Nothing was working. Then I saw that my hard drive would not eject properly after I opened iTunes (Music). So when i open any other application and try to eject the hard drive it's fine, but whenever I open itunes, then i close itunes the hard drive won't eject. I make sure iTunes is completely shut off, but even if its completely quit, it seems the hard drive won't eject unless I force eject it. So I don't know if that means the music library isn't saving. Then yesterday I noticed that the changes I made on each computer wouldn't even save on its own computer. Once i started moving some things around now itunes won't recognize the music AT ALL. So as of right now, I'm ignoring why both computers aren't saving each other's playlists and I'm trying to figure out this new problem. If I hook up my harddrive on my laptop, let's say, when I press my songs , the exclamation point comes up asking to locate my music. I went back  to make sure my location of the folder is fine and it is, It goes to my hardrive, music and the folder where all my music is. Then i checked a specific song and went into its info, each song is going to the correct folder but the music is NOT playing. The only music playing is obviously my purchased songs. So now i cant use my itunes at all and I'm freaking out. I need my music and playlists. If anyone can help, I'm open to any resolution. Im open to phone calls or anything. Thank you dearly for any help. All the best

-Brad 


[Re-Titled by Moderator]


MacBook Air (M2, 2022)

Posted on Mar 23, 2023 9:12 AM

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Posted on Mar 26, 2023 6:54 AM

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5 replies

Mar 24, 2023 1:22 PM in response to Skyman1701

It seems like you have a number of issues here. Perhaps we should start by trying to fix the issue with the broken links. Do you have Home Sharing enabled? With Music the library can be shared even when the app isn't running, which might potential prevent the drive with the content from being ejected.




The "missing file" issue with exclamation marks happens if the file is no longer where iTunes or Music expects to find it. Possible causes are that you or some third party tool has moved, renamed or deleted the file, one of its parent folders, the drive it lives on has had a name change, or you've moved a non-portable library to a different path (see Make a split library portable for details). It is also possible that iTunes or Music have changed from expecting the files to be in the pre-iTunes 9 layout to post-iTunes 9 layout, or vice-versa, and so is looking in slightly the wrong place, or that you've been too aggressive when deleting duplicates at some point.


Select a track with an exclamation mark, use Cmd-I to get Song Info, then click No when asked to try to locate the track. Look on the file tab for the location the library thinks the file should be. Now take a look around your hard drives. Hopefully you can locate the track in question. If a section of your library has simply been moved, a folder renamed, or a drive label has changed, it should be possible to reverse the actions. If the difference between the two paths is an additional Music folder in one path then this is a layout issue. I can explain further if that is the case. If everything is where it is supposed to be try Repair security permissions for iTunes for Mac - Apple Community.


In some cases the library may be able to repair itself if you go through the same steps with Get Info, or when playing a track, but this time click Locate and browse to the lost track. It may then offer to attempt to automatically fix other broken links. Although it says something like "use the same location" I think it expects to find the tracks in the same artist & album layout they were in previously, with one systematic change to the path.


If you want me to try to provide specific advice please post back the following details:

  1. The location of the media folder under iTunes|Music > Preferences > Advanced
  2. The location of a sample missing track shown under Song Info > File > Location that begins file://
  3. The true path to the file whose details you gave in 2



See also FixLinks - an AppleScript to repair broken links in Music - Apple Community.



tt2

Mar 25, 2023 5:37 AM in response to Skyman1701

I suspect each computer has a separate library database. To be able to use the same library across a number of computers you want the Music Library.musiclibrary package stored on the external drive as well as the media. See Managing your Mac media libraries - Apple Community for some background. For best results you likely want to rearrange things such that the database is <External>/Music/Music Library.musiclibrary and the media folder is <External>/Music/Media.


tt2

Mar 24, 2023 7:56 PM in response to turingtest2

I want to thank you first for replying and being so helpful. I just re-did the process telling iTunes (music) to find the songs on the SSD drive and it’s working again. At least for now it’s working I don’t know why it stopped.

The major issue I’m dealing with now is both my iTunes talking to each other again. When I’m sitting on my desktop downloading music and changing playlists etc, when I eject my SSD drive and put it on my labtop then open iTunes. The changes I made on the other computer aren’t on that one. Or vis versa. This worked before for me but for some reason isn’t working anymore. It’s very important that my playlists work on both computers. I would appreciate any insight. Thank you!

Mar 26, 2023 6:55 AM in response to turingtest2

I’m sorry for such a late response. Work was very busy this weekend. Thank you for the input. I did switch everything over to music format and yes I do have everything filed to the external hard-rive, and the music library is there with the media folders as well. I did all of this previously and it never worked. I am uploading screen shots to show where the files are going. Sorry for the mess in the office, rearranging things lol. I have all the files in the correct spot on the external and I have also made sure there is no separate music library somewhere on each computer. But whenever I make a change on one computer it still doesn’t save to the other. My work is on standby sadly because of this. I don’t know what else to do. Thanks so much!!

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iTunes playlists won't sync between both of my Macs

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