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”. 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. There are different boundary cases between a Windows machine and a Mac. The reason behind is that syncing files between different OS isn’t as easy as you thought. Please download the application on this computer and try again”. There’s a problem with the application files. 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. Sometimes when you are using OneDrive on your Mac, you get unexpected error prompt and your OneDrive will not start after.