How to get all the PC files into iCloud? Drag or copy MyDocuments\* into iCloud>Documents?

OK, there’s a step here I’m not picturing. I bought Ms. Napier her first Mac, a Mini. She’s been PC all along. I want to use iCloud to get all her PC content available on the Mac, and give her all the overlap time she wants using both systems.

I have iCloud running on her old PC and her new Mac. There’s an iCloud Drive > Documents folder on the old PC and there’s one on the new Mac. When I put a new file in either of these, it appears in the other, and I can open it. So, there’s a bridge between the PC and iCloud and the Mac, and it works.

What I am not getting is, how do I get all her old PC documents swept up in this new scheme? Do I drag everything from her old MyDocuments folder into the iCloudDrive Documents folder? Then tell her never to use MyDocuments again?

I don’t think I should copy everything from MyDocuments to iCloud Documents, because further work she does on the PC in MyDocuments will change only that copy and there’ll be two versions. Besides, I think that may try to create two local copies on the old PC, for which there may not be enough hard drive space.

Ms. Napier is unsophisticated in computers and afraid of change generally and the Mac particularly, as it is. Something smooth would be really helpful here.

I’m Mac only at home, and simply treat my iCloud Documents folder as my user folder. I’m going to suggest that to her, too.

Thank you!!

I think you understand the situation correctly.
There’s no perfect solution. If you could make move MyDocuments to iCloud drive, and then alias it back to the PC, that would be the best solution, but I’m pretty sure that’s unsupported.

So, I think you need to move the documents she needs to iCloud, and then delete them from MyDocuments. And, see if there’s a way to make the default file storage location iCloud on the PC.

I can’t imagine why Microsoft didn’t think this through better and provide a more straightforward way to facilitate shifting everything toward a Mac.

Oh… wait…

Wait, sorry, not clear exactly what you’re suggesting.

Is it:

  1. Copy MyDocuments content to iCloud
  2. Delete the original MyDocuments content
    (I’m not certain this couldn’t delete everything if something blew up in the iCloud setup, or if it might run out of HD space while copying)

Or is it:

  1. Move MyDocuments content to iCloud, which removes it from MyDocuments (right?)

It depends on how iCloud Drive is implemented on the PC.
If it’s a different volume, a dragging files onto it will copy them, not move them. If so, they will then be in two places, and cause no end of confusion.

Why not Resilio Sync two folders on two computers instead of using iCloud? That way you do not have to move them.