
So this issue has recently appeared on one of my Macs which is doing a large download of around 1TB of sync Data. In short its being download and the whole site is being moved to Dropbox, Sorry Microsoft but Sharepoint is not what it’s cracked up to be, in my humble opinion. If you have encounter a similar issue we go through the causes and some options which might fix the issue.
Why OneDrive Isn’t Transferring Files—Possible Reasons
1. Storage Is Full
If your OneDrive storage has reached its limit, you won’t be able to upload, edit, or sync new files—including Camera Roll items.(Microsoft Support)
2. Upload Issues via Web (Office 365.com)
Several problems can block uploads through the web interface, including:
- Connection drops or being signed out
- Missing permissions (especially in work/school accounts)
- Unsupported file types, empty files (0 bytes), or disallowed characters in file names
- Files that exceed browser or app size limits (web upload limit ~250 GB per file, older browsers limited to 300 MB; desktop app may support much larger sizes)
3. ‘Files On-Demand’ Feature & Online-Only Files
If OneDrive’s Files On-Demand is enabled, files created on another device (like your phone) may remain “online-only” and won’t download to your PC automatically—even if they appear in your OneDrive folder.
4. System or Network Configuration Problems
- Firewall, VPNs, or network filters (e.g., BT Web Protect and Virgin) could interfere with syncing.
- Company or school security policies may block syncing if your device isn’t compliant or registered. This is relocated to the workaround people use to install One Drive app for machines running Monterey and below.
5. Sync Glitches, Software Bugs, or Corruption
- OneDrive may get stuck at “Looking for changes” or “processing changes” and stop uploading.
- Known issues on macOS (e.g. Error -99 or app freezing) have been addressed in updates.
- Users report syncing issues when using external drives for OneDrive—uploads may work initially but fail over time.
6. File Name or Path Restrictions
OneDrive enforces limits on:
- Path length (max ~400–442 characters)
- Filenames containing restricted characters or reserved names like AUX, PRN, CON, etc.(Microsoft Support). This is a common issue with Filenames or length of filename and folder has reached the Max space.
7. Credential & Cache Issues
- Expired or corrupted credentials, Office Upload Center cache, or credential manager entries can block upload operations.Microsoft Support)
8. Paused or Unresponsive Sync
Sometimes sync is paused or unresponsive. While there’s no “Sync Now” button, pausing and resuming sync often helps trigger pending uploads.
9. Work-Account Specific Conflicts
When multiple accounts are in use (personal and work), or device compliance/policies are at play, OneDrive may show syncing symbols but not actually transfer data.

Common Fixes & Workarounds
Basic Checks
- Confirm OneDrive is running and synced correctly (check the system tray icon).
- Pause and resume syncing: Access via the OneDrive icon → Settings.
- Reboot: this can fix the issue
Tackle Storage Issues
- Clear space on your OneDrive or upgrade storage.
- Check local disk space, so OneDrive has room to manage syncing.
Address ‘Files On-Demand’
- Disable Files On-Demand and mark files or folders to “Always keep on this device” for full local sync.
Software Updates & Resets
- Ensure OneDrive, Office, and OS are fully updated.
- Reset OneDrive:
- Use this with caution! While this script does not delete any of your OneDrive files it does completely reset OneDrive on your Mac.
- Open ~/Applications
- Secondary Click on OneDrive.app and choose “Show Package Contents”
- Navigate to Contents/Resources/
- Double click on ResetOneDriveStandalone.command
- Then restart the app.
- Unlink and re-link your account: OneDrive icon → Settings →Preferences → Account tab.
Permissions, Paths, & File Issues
- Rename or shorten files/folder paths if they’re too long.
- Remove special characters or reserved names from file/folder names.
- Ensure files aren’t open or blocked.
External Drive Caution
- If syncing from an external drive, consider moving OneDrive folder structure into your internal drive. Or use OneDrive’s default location.
Clear Cache and Credentials
- Clear Office Upload Center cache and delete OneDrive/Office credentials via Credential Manager.
Corporate Accounts & Compliance
- Test uploading via the web (portal.office.com). If that works, the desktop app may be blocked due to compliance policies.
- Ensure your device is compliant or registered with Intune or your corporate network.
- If syncing hangs, try identifying the stuck file (check icons, move it temporarily, etc.).
Recap Table
| Problem Type | Tips to Fix |
|---|---|
| Full storage | Free up space or upgrade OneDrive |
| Files On-Demand | Disable it and set files to keep local |
| Long paths / bad names | Shorten or rename files/folders |
| Stuck sync (desktop app) | Reset, unlink/relink, update, then restart OneDrive |
| External drive problems | Move to internal drive or original OneDrive folder |
| Network or policies | Check firewall, VPN, or corporate device compliance |
| Upload via web | Use OneDrive.com to test if account is functional |
| Credential/cache errors | Clear cached credentials and related Office/OneDrive cache |
| Pause/resume stuck sync | Manually pause and resume syncing via settings |
Final Thoughts
If OneDrive can’t transfer files right now, it’s likely due to one (or multiple) of the reasons outlined—anything from full storage to after-effects of a reset, or even company-level restrictions. The solutions above cover each level to help you troubleshoot more methodically. On this occasion the account had reached the download limit for that machine and kicked back in within 12 hours. If the machine was taken away and booted on a different ext IP address it might have kicked back in but this is a theory. It also highlights a limitation to using OneDrive and Sharepoint for large file transfers. It might be worth looking at Dropbox or Box as a different solution.



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