OneDrive Finder Integration Missing After macOS Update

After updating macOS, many OneDrive users find that Finder integration features such as the sync status overlay icons, right-click menu actions, and the OneDrive folder shortcut in the Finder sidebar have disappeared. This typically happens because macOS updates reset or disable the Finder Extension that OneDrive installs to integrate with the file system. This article explains why the update breaks the integration and provides step-by-step instructions to restore all Finder integration features in OneDrive for Business.

Why macOS Updates Disable OneDrive Finder Integration

macOS updates, especially major version upgrades like Ventura or Sonoma, can disable third-party Finder Extensions as part of Apple’s security hardening. The OneDrive Finder Extension, which provides the green checkmark and other sync status icons, is registered as a system extension. When macOS updates, it may reset the list of approved extensions, leaving OneDrive unchecked. Additionally, the update process can remove the OneDrive folder from the Finder sidebar and reset the right-click contextual menu items. The integration itself is not broken, only disabled, so you can re-enable it without reinstalling OneDrive.

Steps to Re-enable OneDrive Finder Integration

Follow these steps in order. After each step, check if the integration is restored before moving to the next.

1. Enable the OneDrive Finder Extension in System Settings
   Open the Apple menu and select System Settings. Click Privacy and Security in the left sidebar, then scroll down and click Extensions. In the Extensions window, click Finder Extensions from the list. Find OneDrive in the list and check its checkbox. If OneDrive is not listed, close System Settings, restart the Mac, and check again.
2. Toggle the OneDrive Finder Integration Setting
   Open OneDrive preferences by clicking the OneDrive cloud icon in the menu bar, then click the gear icon and select Preferences. Click the Finder tab. Uncheck the box labeled Show sync status icons in Finder. Wait five seconds, then check the box again. This forces OneDrive to re-register its Finder Extension with the operating system.
3. Restart Finder
   Hold the Option key on your keyboard, then right-click the Finder icon in the Dock. Select Relaunch from the context menu. If Finder does not appear in the Dock, open Terminal and run the command: killall Finder. After Finder restarts, open a Finder window and check if the OneDrive folder appears in the sidebar and if overlay icons show on files.
4. Restart the Mac
   If the integration is still missing, restart your Mac completely. Click the Apple menu and select Restart. After the Mac boots up, sign in and check Finder again.
5. Reinstall OneDrive as a Last Resort
   If none of the above steps work, uninstall OneDrive and install the latest version. Download the OneDrive installer from the Microsoft 365 admin center or from the official OneDrive download page. During installation, allow the Finder Extension when prompted by macOS.

If OneDrive Finder Integration Still Has Issues

OneDrive Overlay Icons Not Showing After Re-enabling Extension

If the extension is enabled but overlay icons still do not appear, the icon cache may be corrupted. Open Terminal and run: sudo rm -rf /Library/Caches/com.apple.iconservices; sudo killall Finder. Enter your admin password when prompted. This clears the icon cache and forces Finder to reload all icons, including OneDrive sync status icons.

OneDrive Folder Missing from Finder Sidebar

If the OneDrive folder does not appear in the Finder sidebar after enabling the extension, add it manually. Open a Finder window and press Command+Shift+G. Type ~/Library/CloudStorage and press Enter. Locate the OneDrive folder for your organization, then drag it to the Favorites section in the Finder sidebar. This restores quick access to the OneDrive folder without relying on the automatic sidebar entry.

Right-Click Menu Missing OneDrive Options

If right-clicking a OneDrive file does not show options like Share or View online, the Finder Extension may be partially loaded. Go back to System Settings > Privacy and Security > Extensions > Finder Extensions. Uncheck the OneDrive checkbox, wait ten seconds, then check it again. Then restart Finder using the Option+right-click method. This fully reloads the extension and restores the contextual menu items.

Finder Integration Features: Enabled vs Disabled

Feature	Enabled	Disabled
Sync status overlay icons	Green checkmark, blue sync arrows, or red X appear on files and folders	No icons visible; files appear as regular local items
Right-click contextual menu	Options to Share, View online, Copy link, and manage file permissions	Only standard macOS right-click options appear
Finder sidebar shortcut	OneDrive folder appears under Favorites or Locations	No OneDrive entry in sidebar
Files On-Demand behavior	Placeholder files download on demand when opened	Files are always downloaded or always online-only depending on setting

After a macOS update, all three features may be missing. Re-enabling the Finder Extension restores all of them at once. If only one feature is missing, use the corresponding fix in the section above.

You can now restore OneDrive Finder integration after any macOS update by re-enabling the extension in System Settings and toggling the Finder preference in OneDrive. Next time you update macOS, check the Finder Extensions list immediately after the update completes. As an advanced tip, you can create a macOS shortcut that opens System Settings directly to the Finder Extensions pane for faster access: use the URL x-apple.systempreferences:com.apple.preference.security?extension with the Shortcuts app.