I'm running Parallels 11 with Mac El Capitan and Win 10, and Office 365 plus OneDrive installed on the Win side. Am natively sharing my Desktop, Documents and Downloads folders between Mac/Win thru Parallels but I'd also like to sync them both with OneDrive.

I don't want to use symlinks as OneDrive can't accept these, and if possible want the ability to shutdown my Win and run Mac on its own - so I'm thinking I need to customise the Win locations of each folder to OneDrive, and then use Offline Files or similar to sync with the Mac.

Am not wanting an external sync program because from what I've seen they're not real robust unless its a service and watching for changes at a low level like OneDrive does, and I don't want scheduling. Also need to run a large search index on the Win side as I have over 0.5m files including 50Gb email, and need this native to Win - so I can't run OneDrive on the Mac.

A tough one.! . . . . . . . any suggestions.?

  • The Desktop, Documents and Download folders are specific system folders with specific permissions etcetera, not just 'any' shared folder. I don't think it's as simple as you suggest, I've tried. In any event I think symlinks would be required on one or maybe both sides doing it your way unless I'm mistaken. I'm currently using OneDrive on Windows and Mac as a temporary solution but as its a laptop it uses WAN and in many cases when I'm using mobile hotspot especially while travelling overseas blows my data limits. My use case is that I'm wanting a three way live sync of each of the above three Jun 23, 2016 at 16:03
  • Did you mean to create an answer or comment on the other answer? This seems more like a comment than an answer.
    – Chillie
    Jun 23, 2016 at 16:07
  • I meant to comment but couldn't see a comment box - sorry, originally created on web then commented on iPhone app Jun 23, 2016 at 16:19
  • You could always update your question. Instead of creating an answer that is a comment.
    – Chillie
    Jun 23, 2016 at 16:21
  • Understand - I've taken the lesser of two evils rather than including a response in my question - will keep it all on one platform from now on . . . -:) Jun 23, 2016 at 16:25

1 Answer 1


OneDrive allows you to sync to whatever folder you desire. In your case, point it to a OneDrive folder in the shared Windows document folder. The Mac will simply have this folder in its Document folder as well. Whenever Windows is running, it will sync with Onedrive and populate the shared folder. Of course, since you don't have OneDrive on the Mac, it won't sync. You could always put OneDrive on the Mac, and point it to the same folder...

  • Could having both OSX and Windows point at the same folder possibly cause a conflict? What if they both try to sync to it at the same time?
    – Chillie
    Jun 23, 2016 at 16:32

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