Unbroken1 Don’t think so mate. Seemed to be happening to quite a few people on socials which is where I found the ‘fix’. Before that had pulled quite a few tracks out from Apple Music into a desktop folder to use in an Ableton mix and ended up losing them when I deleted the folder and emptied the bin. While the bin is still full the file location just moves there, and plays ok, but emptying the bin loses the file. They still appear in the Music app song list but I get a [!] sign when I tried to play them. e.g. Luke Brancaccio here…
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Topic: Moving songs to Desktop/USB → deleting them → Apple Music “loses” the original file.
🧱 1. UNDERSTANDING WHAT’S REALLY HAPPENING
Even though it seems like you’re only moving a copy, Apple Music does not always create a duplicate when you drag a file out of the app.
✔ What is most likely happening:
When you drag a song from Apple Music to the desktop or a USB drive, macOS sometimes moves the original file, NOT a duplicate.
Then, when you delete that file you moved…
➡️ You’re deleting the only real copy.
➡️ Apple Music is left pointing to a path that no longer exists → “missing file”.
This behavior changed because of how Apple Music handles “Master,” “Optimized,” and local files starting in macOS Ventura and Sonoma.
⚙️ 2. JUST BECAUSE IT DIDN’T HAPPEN BEFORE DOESN’T MEAN YOUR SETTINGS DIDN’T CHANGE
Apple has silently modified:
•how dragging files works (copy vs move),
•how Manage Music Library behaves,
•how it handles local files vs Apple Music/iCloud Music Library assets.
Even if you didn’t change your settings, the system’s behavior may have changed on its own (automatic updates = different behavior).
📌 3. WHAT YOU NEED TO CHECK (CRITICAL)
A) Apple Music Preferences
Open Music → Settings → Files
Check this:
🔲 “Copy files to Music Media folder when adding to library”
This MUST be ON if you want Apple to keep its own internal copy of everything you add.
If it’s OFF, Apple Music references the original file, so moving it in Finder breaks everything.
Probable cause: this checkbox got turned off without you noticing.
📌 4. WHAT YOU SHOULD DO TO AVOID LOSING FILES
🟦 Safe option (recommended)
- Turn on “Copy files to Music Media folder…”
- Close and reopen Apple Music.
- For files already in your library: select all → File → Library → Consolidate Files.
This forces Apple Music to:
Create its own internal copies
Organize everything
Stop depending on scattered files in your system.
—
📌 5. HOW TO EXPORT SONGS WITHOUT BREAKING THE LIBRARY
As of macOS Ventura:
Dragging with Option (⌥) → forces copy
Dragging without modifiers → might move the original file (inconsistently depending on the source folder)
🟩 To play it safe every time:
➡ Drag with the Option (⌥) key held down
This guarantees that ONLY a copy is created on your Desktop/USB.
—
📌 6. OTHER IMPORTANT CHECKS
A) If you use iCloud Music Library.
Apple Music tries to manage local-only vs cloud files.
iCloud may mark files as “Optimized” and relocate the original.
B) If your Music Media Folder is on an external drive.
macOS sometimes unmounts it on restart, and Apple Music thinks the folder disappeared.
—
🎯 7. PRECISE SUMMARY (FINE SERRUCHO)
- Apple Music is moving files when you think it’s copying them.
- By deleting the “copy,” you’re actually deleting the original.
- This stopped working the old way because of system behavior changes, not your settings.
- Technical fix:
Enable “Copy files to Music Media folder…”
Consolidate the library.
Use Option (⌥) when dragging files out.
