Summary
This article explains how to fix a drag-and-drop issue in macOS Tahoe where files cannot be moved from a local folder to OneDrive-redirected folders (such as Documents or Desktop) in the Finder sidebar. The issue occurs when OneDrive's Known Folder Move feature is enabled, causing the original macOS folders to become locked. Resetting the Finder sidebar shortcuts resolves the problem.
Body
Issues
- I cannot drag and drop files to the Documents or Desktop folder in the Finder sidebar on macOS Tahoe.
- Why can't I drag files from Downloads to Documents in Finder on my Mac?
- My OneDrive Documents folder in the Finder sidebar won't accept dragged files.
- Drag and drop from a local folder to a OneDrive-redirected folder is not working in macOS Tahoe.
- Files won't move to my Documents or Desktop folder in Finder after OneDrive Folder Backup was set up.
- The Documents and Desktop folders in my Finder sidebar appear locked or unresponsive when I try to drag files into them.
- OneDrive Folder Backup is on and now I can't drop files into my Desktop or Documents folder in Finder.
- Why does dragging a file to Documents in the Finder sidebar do nothing on my Mac?
Environment
This issue affects Bowdoin faculty, staff, and students using Bowdoin-issued Mac computers running macOS Tahoe (26.x) with OneDrive (work or school account) installed and OneDrive Folder Backup enabled. OneDrive Folder Backup redirects your Desktop and Documents folders from local Mac storage to OneDrive cloud storage.
- Affected devices: Bowdoin-issued MacBook Pro, MacBook Air, iMac, Mac Mini
- Affected OS: macOS Tahoe (26.x)
- Affected software: OneDrive for work or school with Known Folder Move enabled
- Not in scope: Windows drag-and-drop issues with OneDrive — see OneDrive Troubleshooting on Windows in the Related Articles section if you are on a Windows device.
Resolution
Reset OneDrive-Redirected Folders in the Finder Sidebar
When OneDrive OneDrive Folder Backup is enabled, OneDrive replaces your local Desktop and Documents folders with redirected versions that sync to the cloud. In macOS Tahoe, the original folder shortcuts that Finder added to the sidebar can become locked, preventing drag-and-drop into the new OneDrive-backed locations. Removing and re-adding these folders in Finder Settings forces Finder to recognize the correct, active OneDrive folders.
- Open a Finder window by clicking the Finder icon in the Dock (the blue and white smiley face icon).
- In the menu bar at the top of the screen, click Finder, then select Settings.
- In the Finder Settings window, click the Sidebar tab.
- Locate the Documents and Desktop checkboxes under the "Favorites" section.
- Uncheck the Documents checkbox. Then uncheck the Desktop checkbox.
Note: Unchecking these boxes removes the shortcuts from the Finder sidebar temporarily. Your files are not deleted — they remain safely in OneDrive.
- After both boxes are unchecked, re-check the Desktop checkbox, then re-check the Documents checkbox.
- Close the Finder Settings window by clicking the red close button in the top-left corner of the window.
- In the Finder sidebar, confirm that Documents and Desktop now appear under Favorites. These shortcuts now point to your OneDrive-redirected folders.
- Test the fix by dragging a file from your Downloads folder to Documents in the Finder sidebar. The file should move or copy successfully.
Additional Help
If you need further assistance, you have several options:
- Bowdoin Bot: Chat with Bowdoin Bot directly from any KB page for instant answers.
- Phone: Call the Bowdoin College Service Desk at (207) 725-3030.
- In person: Visit the Tech Hub in Smith Union during business hours.
- Submit a ticket: Request assistance through the Service Catalog.
Additional Resources
AI-assisted content: This article was created with AI. It was verified and edited by a human.