I love to live on the bleeding edge and Dropbox just loves to have fun with me in the process. It’s one of my old tried and true apps and I love the hell out of it. I willingly pay for the subscription and I store so many terabytes of data on it but really it’s coming to a head when I’m playing with fire (aka beta software). I installed a new macOS Tahoe (Beta 1, and just upgraded to Beta 2), and I’ve been playing with it, and it has been working great, but for some reason, the Dropbox client loves to nuke all of my desktop download folder and document folder permissions, resulting in a massive headache.
I had to set up macOS as a USB bootable installer using the full download PKG and reinstall my computer and use Time Machine to be able to grab all the files and restore the backup. And I was able to do that only for Dropbox to nuke my permissions again.
I’ve been now focused on running an advanced reinstall, and I look at the beta builds regularly to see if there is any that are going to help solve these problems. Long story short: don’t use beta software on production systems.
Now I’m living the dream of recovering my computer over and over again. I should just regress back, but God, I love the shiny new stuff, and who doesn’t love a little bit of glass on every UI? Apparently the internet does not love it, but it tickles all my fancies. It’s kind of nice to see Windows Vista’s dream realized in the hardware and software stack of a Mac.
Anyways, ymmv, be warned!
Edit: Why did I not just use OpenAI’s o3 from the beginning to help me. Once I gave it clear context, it gave me a great way to solve the issue myself.
Here it is for those who may be stuck with the same issue
Fix “You don’t have permission to see its contents” when using Dropbox Backup
Problem: Dropbox Mac Backup creates permission issues with Desktop, Documents, Downloads folders.
Solution: Remove Dropbox backup links while keeping all files intact.
Steps
1. Disable Mac Backup
- Open Dropbox menu → Preferences → Backups → Manage backups
- Click Stop backup (or Delete backup) for Desktop, Documents, Downloads
- Dropbox automatically moves folders back to
~/Desktop,~/Documents,~/Downloads
2. Fix File Permissions
sudo chown -R "$USER":staff ~/Desktop ~/Documents ~/Downloads
chmod -R u+rwX ~/Desktop ~/Documents ~/Downloads
3. Clear System Flags
diskutil resetUserPermissions / "$(id -u)"
killall Finder
4. Optional: Re-enable Dropbox Sync (without backup)
- Relaunch Dropbox
- Preferences → Sync → Folders in Dropbox — uncheck Desktop, Documents, Downloads
- Grant Full Disk Access: System Settings → Privacy & Security → Full Disk Access
Why This Works
- Mac Backup replaces real folders with aliases in
~/Library/CloudStorage/Dropbox/ - Disabling backup restores actual folders
- Commands fix POSIX permissions and remove problematic ACLs
Safety Backup (Optional)
mkdir -p ~/Desktop/_safety_copy
cp -a ~/Library/CloudStorage/Dropbox/{Desktop,Documents,Downloads}/* ~/Desktop/_safety_copy/
Note: No files are deleted. You’re only removing Dropbox’s backup connection.