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macrumors member
Original poster
Feb 24, 2020
Minnesota USA
I've been maintaining my iTunes library since I started using it in 2004. I have many playlists, ratings, count plays, etc. I'd like some help moving my existing iTunes library from my Windows 11 PC over to my Mac Pro.

I've been able to figure out getting the music files onto the new Mac, but I haven't been able to figure out how to get my counts, playlists, and such to work with the new Music app. Any help in figuring this out would be appreciated.


macrumors 65816
Aug 31, 2010
There may be solutions to migrate a Windows iTunes library to a Mac but none of them worked to my satisfaction.
If others succeeded and chime in, you can stop reading.

I will at least report how I solved it.
For macOS almost everything can be achieved by making use of AppleScript to transfer tags and metadata.
For Windows, the possibilities are very limited. I'll link it anyways.

I'm assuming you have actual music files that you have transferred to your Mac and those songs reside in the same folder sub structure as on Windows.

Playlists (Smart playlists will get transformed to regular ones):
On your Windows iTunes, you can manually export each playlist by selecting it in the left sidebar and click
File > Library > Export playlist... and choose *.m3u
Before importing said playlist file on your Mac, you have to open it with a text editor and search and replace the old Windows path with your new Mac path. A.e.:
Search for "D:\Music" and Replace by "/Volumes/Music"
and Search for "\" and Replace by "/"

The only way I have found to transfer ratings and play counts is a bit more time consuming but uses the similar approach:
On Windows, create a smart playlist for each of your ratings (0 to 5 stars) and export those playlists.
Perform the same search and replace action as above before importing the playlists on your Mac.
Then you can select all songs of a playlist and set the appropriate rating.

Play counts:
Same for play counts: To simplify things, I created 10 smart playlists with different play count ranges. The increment depends on your actual numbers. I chose 20 from 1-20 up to ≥180.
Export, modify and import the playlists same as above.
Then select all songs of one playlist and decide upon a single play count value that you want to assign to all of those songs.
To update the play count value of the songs, use the following AppleScript:
tell application "Music"
    set sel to selection
    set dialog_answers to display dialog "Enter a new play count:" default answer ""
    set newcount to text returned of dialog_answers as integer
    repeat with t in sel
        if button returned of dialog_answers is "OK" then
            set played count of t to newcount
        end if
    end repeat
end tell
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macrumors 68020
Nov 22, 2007
Aalborg, Denmark
I would have thought that moving all related iTunes Libraries over to the Mac having the same structure as on Windows.

Then use that Retroactive app available on GitHub (assuming it still works with Sonoma)

Next I would install the latest iTunes available from inside Retroactive, open iTunes after the process is done.

Have iTunes read from the copied Windows iTunes folder and open the correct Library for iTunes.. if you see your Windows iTunes perfectly mirrored onto the macOS iTunes (via Retroactive) then I would guess that if you then open the Music app on macOS after quitting iTunes (CMD+Q) and have Music app read that iTunes Library and update for use with the Music app.

Music app will/my hope is that it will - update the iTunes Library for use with Music. I remember it being so when Music app was introduced and people only had their iTunes app installed. First launch of Music would have it read the existing iTunes Library files and update them.

I don't imagine it's as simple as renaming a bunch of iTunes library files to match those of Music

I hope and pray that's the solution.

Of course, as always.. backup, backup.

Retroactive is here in case you want to experiment with it.
Retroactive on GitHub
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macrumors member
Original poster
Feb 24, 2020
Minnesota USA
I do have my data backed up pretty well. I might try that Retroactive app. Another thought I have is that I still have my Mojave drive from my 5,1. I could copy my Windows iTunes library to the Mojave drive, and put it in the 7,1 and see if I can transfer that way... We will see.
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