Folder Sync Not Working

“Folder Sync Not Working” occurs when entire subdirectories within your cloud storage path fail to synchronize, even though individual files in other directories sync correctly. Affected folders may display a perpetual “sync pending” icon, fail to show up in the web console, or disappear locally due to selective sync or virtual drive conflicts.

This guide provides procedures to audit symbolic links, reset system folder redirection conflicts, and flush local index caches on both Windows and macOS.

---

1. Understand Folder Sync Issues

Folder sync anomalies are usually triggered by:

• Symbolic Links and Junction Points: Cloud clients typically ignore symbolic links (symlinks) or directory junctions. If you try to sync a folder containing symlinks, the sync client will freeze or skip them.
• Selective Sync Configuration: The folder was unchecked in the client settings on this device, preventing it from downloading.
• System Folder Redirection Conflicts: Windows Folder Redirection (mapping Desktop or Documents to a server share) or macOS iCloud Desktop syncing interfering with third-party sync folders.
• Corrupted Directory Cache: Application cache stores holding broken folder trees or orphaned directories.

---

2. Resolve Folder Redirections and Symlinks on Windows

On Windows, you must find and remove incompatible directory junctions and audit folder paths.

A. Locate and Remove Directory Junctions (Symlinks)

Use Command Prompt to list all junctions in your sync path:

1. Search for Command Prompt in the Start Menu, right-click, and select Run as Administrator.
2. Run the directory query command:

   # Scan the OneDrive folder for junction points
   dir "%UserProfile%\OneDrive" /al /s

3. If any lines return <JUNCTION> or <SYMLINKD>, delete the junction point using:

   # Remove a directory junction (retains the original files at source)
   rd "%UserProfile%\OneDrive\PathToJunction"

B. Disable Group Policy Folder Redirection Mismatch

If corporate GPOs redirect your system folders, OneDrive or Google Drive cannot sync them directly:

1. Press Win + R, type rsop.msc (Resultant Set of Policy), and press Enter.
2. Navigate to User Configuration > Windows Settings > Folder Redirection.
3. Verify if your Documents or Desktop folders are forced to network paths. If so, contact your IT administrator to exclude your machine from this GPO to enable cloud sync.

---

3. Fix Directory Permissions and Cache on macOS

On macOS, you can reset directory system attributes and delete the client’s internal caches.

A. Remove Stale Finder and Cache Directories

1. Open Terminal (via Spotlight).
2. Clean out hidden temporary caches that store folder hierarchies (example for Dropbox):

   # Terminate the Dropbox application
   killall Dropbox
   
   # Clear the local cached database files and folder attributes
   rm -rf ~/Library/Application\ Support/Dropbox/cache

B. Fix Folder Extended Attributes (xattr)

If folders carry restricted flags that prevent the sync daemon from listing contents:

# Strip metadata attributes that block indexing from folders
xattr -rc ~/Library/CloudStorage

C. Verify Directory Path Constraints

Ensure the folder names do not contain trailing periods or spaces, which macOS allows but cloud APIs reject:

# Search for folder names containing leading or trailing whitespace
find ~/Library/CloudStorage -type d -name " * " -o -name "* "

Manually rename any directories found with spaces at the end of their name.

---

4. Rebuild the Local Folder Index and Database

If folder sync remains broken, force a clean database rebuild of the application catalog.

Force Selective Sync Refresh

1. Click the sync client icon in the taskbar or menu bar.
2. Go to Settings / Preferences > Sync > Choose Folders.
3. Uncheck the folder that is failing to sync.
4. Click Apply or Save. This will delete the local folder copy from your disk.
5. Wait 2 minutes, reopen Choose Folders, re-check the folder, and click Apply. The client will download a fresh copy from the cloud.

---

5. Summary Quick Reference Checklist

Action Target	Operating System	Terminal Command / Path	Expected Outcome
Search Junctions	Windows	dir "%UserProfile%\OneDrive" /al /s	Locates folder links that block the sync engine.
Delete Junction Link	Windows	rd <path>	Removes the link safely without deleting source data.
Verify Redirections	Windows	rsop.msc	Identifies network folder mapping conflicts.
Clear Dropbox Cache	macOS	rm -rf ~/Library/Application\ Support/Dropbox/cache	Forces Dropbox to rebuild folder metadata.
Strip Folder Attributes	macOS	xattr -rc ~/Library/CloudStorage	Removes system flags blocking directory indexing.
Selective Sync Toggle	Client Settings	Preferences > Choose Folders	Re-synchronizes a target folder from the cloud.