Troubleshooting
OneDrive Not Syncing on Mac? Here's the Fix
OneDrive on Mac stuck pending, missing files, or hung at 'Looking for changes'? Here's the troubleshooting flow that actually works.
You drop a Word document into your OneDrive folder, and the cloud icon next to it just… sits. The little OneDrive cloud in the menu bar says “Looking for changes” and has been saying that for an hour. Or files synced fine yesterday, and today nothing leaves your Mac.
OneDrive on Mac has a reputation for sync flakiness, partly because of how Microsoft layered its sync engine on top of macOS’s File Provider API in 2021, and partly because Microsoft updates the client more often than Apple’s frameworks do. Here’s how to get sync working again.
Step 1: Check OneDrive’s status
Click the OneDrive cloud icon in the menu bar. The dropdown shows current state:
- “Up to date” → working.
- “Looking for changes” → scanning, normal for the first few seconds.
- “Looking for changes” for more than 5 minutes → stuck.
- “Sync paused” → manually paused, or auto-paused due to network.
- “Out of date” → conflict, click for details.
Also click the gear icon → Activity Center for a per-file view of what’s syncing or stuck.
Step 2: Quit and relaunch OneDrive
Click the menu bar icon → gear → Quit OneDrive. Confirm. Then relaunch from Applications or Spotlight.
A clean relaunch is the simplest fix. The OneDrive client is running multiple processes (OneDrive, OneDrive Standalone, FileProvider extension), and one of them often hangs without crashing. Restart catches that.
Step 3: Check the File Provider extension
OneDrive on macOS 12.3+ uses Apple’s File Provider framework, which means OneDrive shows up as an external file source rather than a local folder. The extension is what does the sync.
Check it’s loaded:
pluginkit -m | grep -i onedrive
You should see at least one entry like com.microsoft.OneDrive-mac.FileProviderExt.
If it’s not loaded:
killall onedrive
killall "OneDrive Standalone Updater"
Relaunch OneDrive. The extension auto-registers.
Step 4: Sign out and back in
Click OneDrive icon → gear → Settings → Account tab → Unlink This Mac. Restart OneDrive. Sign in again.
This re-issues all auth tokens. If your work account uses conditional access policies (corporate networks, geographic restrictions), the new sign-in will pick up policy changes that may have caused sync to stop.
Step 5: Check storage space
OneDrive needs free local disk to download files (even with Files On-Demand enabled, scratch space is required).
Apple menu → About This Mac → More Info → Storage Settings. Free up space if you’re under 10% remaining.
Also check OneDrive cloud quota: log into onedrive.com → settings → “Storage.” If you’re at 100%, uploads silently fail.
Step 6: Check the file path length
This catches everyone with deep folder structures. OneDrive enforces a path length limit:
- Total path (drive + folders + filename): ~400 characters.
- Filename alone: 255 characters.
If you sync a folder that contains a deeply-nested project, files near the bottom of the tree will fail. The OneDrive Activity Center lists the failed files; if the path is long, that’s the problem.
Move the affected files closer to the root of OneDrive.
Step 7: Check for unsupported characters
OneDrive rejects file names containing:
/ \ : * ? " < > |
It also rejects names like .lock, desktop.ini, CON, PRN, files starting with _vti_, and a handful of other Microsoft-reserved names.
Activity Center → Sync issues → see which files OneDrive flagged. Rename them.
Step 8: Reset OneDrive
If the problem persists, do a full reset:
- Quit OneDrive.
- Open Terminal:
/Applications/OneDrive.app/Contents/Resources/ResetOneDriveApp.command
For business accounts:
/Applications/OneDrive.app/Contents/Resources/ResetOneDriveAppStandalone.command
- Relaunch OneDrive. Sign in.
This wipes the local OneDrive database and rebuilds it. Sync will be slow for the next hour as it rescans everything.
Step 9: Check for File Provider extension conflicts
If you have multiple cloud sync clients running (OneDrive + Google Drive + Dropbox + iCloud), they all register File Provider extensions. Conflicts between them are rare but real.
pluginkit -m | grep -i fileprovider
If you see extensions from cloud apps you no longer use, those are stuck. Microsoft has issued advisories specifically about leftover Box and older OneDrive extensions interfering with new ones.
Removing them:
pluginkit -e ignore -i com.example.fileproviderext
Or, more reliably, fully uninstall the parent app and let macOS clean up the extension. Sweep’s app uninstaller catches File Provider extensions that drag-to-trash leaves behind.
Step 10: Check the network
OneDrive needs to reach *.onedrive.com, *.sharepoint.com, and a constellation of Microsoft 365 endpoints. A VPN, a corporate firewall, or a captive portal can block them.
Test:
ping onedrive.com
curl -I https://login.live.com
If those fail, you have a network problem unrelated to OneDrive. If they succeed but sync still fails, check whether your VPN or corporate proxy is intercepting Microsoft traffic.
A VPN’s network extension can block OneDrive even after the VPN app is uninstalled:
systemextensionsctl list
Remove leftover extensions if any.
Step 11: Check for “Files On-Demand” vs “always available”
OneDrive’s “Files On-Demand” feature makes files cloud-only by default. They download when accessed. If you expected a file to be local but it’s not:
Right-click the file in Finder → “Always keep on this device.” It downloads now.
If you tried that and it stayed cloud-only, the issue is sync, not Files On-Demand.
Step 12: Resolve sync conflicts
When a file is edited in two places, OneDrive creates a conflict copy named like Document-conflict-Mac-2024.docx. Sync sometimes hangs around unresolved conflicts.
Activity Center → Sync issues → resolve each conflict (keep, replace, or merge). After all conflicts are clear, sync resumes.
Step 13: Update macOS and OneDrive
Old combinations cause real bugs:
- OneDrive 23.x and earlier had File Provider issues fixed in 24.x.
- macOS 14.0-14.3 had File Provider regressions fixed in 14.4.
Update both. Microsoft AutoUpdate (open the OneDrive menu → gear → Settings → About → Check for Updates) and macOS Software Update.
Step 14: Switch to “always download” mode (if you have the disk)
If File Provider is causing too much trouble, you can configure OneDrive to download everything locally instead of using on-demand:
OneDrive Settings → Preferences → “Files On-Demand” → choose “Download files as you use them” or use the Activity Center to right-click → Always keep on this device for everything.
This uses more disk but eliminates File Provider as a failure point.
Step 15: When OneDrive is just being OneDrive
Some realities:
- OneDrive on macOS is significantly slower than on Windows for large libraries.
- A library of 100,000 files will take days to fully sync the first time.
- Occasional “looking for changes” hangs of 5-10 minutes are normal under load.
- If your file is over 250 GB, OneDrive will refuse to sync it.
Most “OneDrive not syncing” cases on Mac are fixed by Step 2 (relaunch), Step 8 (reset), or Step 9 (File Provider cleanup). The reset script is Microsoft’s official troubleshooting tool — try that before doing anything more drastic.