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  1. Re: OneDrive sync client - Windows vs Mac OneDrive for PC is way more integrated to the OS, you can share from Shell by right clicking documents etc. OneDrive Mac currently does not have Files on Demand and or any context menu integration.
  2. The new OneDrive sync client lets you sync files from your OneDrive for Business and even from SharePoint sites if your admin enabled it. (If you're the IT admin for your organization, see Enable users to sync SharePoint files with the new OneDrive sync client.) Note: The new OneDrive sync client.

Sometimes when you are using OneDrive on your Mac, you get unexpected error prompt and your OneDrive will not start after. This guide will help you troubleshoot and understand the reason behind some of those errors and why your Mac can’t restart OneDrive after encountering such error.

When you install the OneDrive app for Mac, a copy of your OneDrive is downloaded to your Mac and put in the OneDrive folder. This folder is kept in sync with OneDrive. If you add, change, or delete a file or folder on the OneDrive website, the file or folder is added, changed, or deleted in your OneDrive folder and vice versa.

Troubleshoot OneDrive Error Messages

“OneDrive can’t start. There’s a problem with the application files. Please download the application on this computer and try again”. Such error message isn’t very helpful. The reason behind is that syncing files between different OS isn’t as easy as you thought. There are different boundary cases between a Windows machine and a Mac. If you have large amount of the files using OneDrive to sync files between two different operating systems, the chances are that not every single file can be synced due to various file system limitations between the two OS.

In another case, the error message is more useful, in which it tells you that the reason OneDrive folder has stopped syncing is because “a file or folder can’t be downloaded because the path is too long”. This might not be an issue on Windows OS where it might be originated, but as you can see Mac OS X can’t handle a file with that long path.

To fix both problems requires you to identify and rename the problem file or folder on Windows OS and restart the OneDrive setup wizard on your Mac.

If you are unable to restart the setup wizard within the OneDrive already on your Mac, then you need to delete the app from Dashboard and re-install OneDrive from Mac App Store.

From here you can restart the setup wizard to map out where the OneDrive you’d like to be positioned on your Mac.

It is entirely OK ,to pick the exact same location of the original OneDrive as long you’ve fixed the issue of the specific file or folder that caused the sync to stop.

Another way to fix the sync problem without modifying the file or folder name is to selectively cherry pick the specific folder out of the sync list. If you really need the problematic file you can download via OneDrive web interface.

By doing the above, you should be able to restart the OneDrive syncing process.

File or Folder path length isn’t the only problem

The above example we’ve encountered is due to the file name/ folder path length limitation, but this limitation is just the tip of the iceberg. There are many other file system limitations that are different between Windows and Mac. To give you an example, you can name a file called “AUX” on Mac but the exact same file cannot be created on Windows. Hence, if you have added a file like this in your Mac’s OneDrive, it will be fine, but when Windows OneDrive client picks up this file it will encounter an error. Interesting right ? If you are curious about those limitations and differences check out this detailed TechNet documentations on file naming.

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A side note, if you have Dropbox you can even do further experiment between the different implementation of how Dropbox and OneDrive syncs those file. It’s interesting to see how the same file structure would work when you set up sync using Dropbox instead of OneDrive or vice versa.

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Hi Rudi,

Client

Please first check if you are using the latest version of the OneDrive sync client for Mac. If no, update the version, restart the Mac and perform a sync again to see the result. I’d also like you to upload a screenshot showing the version of the client you are using now for clarification.

Meanwhile, check if the issue happens in some specific files. I suggest you back up the affected files, remove them in the sync process, wait the sync progress to be finished, wait some time and then re-add the files to the sync folder to see the result. Moreover, check if the issue happens when syncing the files to a specific library in a specific site and check if there are some limitations the article mentioned in the affected files.

If you change a network environment, what’s the outcome? Can the files be synced with the sync client for Mac on other users' Macs?

Thanks,

Cliff

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