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Selfhosted
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Maybe install the nextcloud client on his PC and have him copy over the files there. The Nextcloud client has sync and resume functionality and you don't have to watch it like a hawk. It just does it's thing in the background.
Huh yeah that's not a bad idea. I actually sort of dislike the nextcloud client normally (as I'd prefer it to not actually download the remote files, but act like a virtual filesystem). But in this case, it might actually work...
It acts as a virtual file system on Windows.
Oh, didn’t know that. Sadly I’m only on Mac & Linux
I believe it is able to do so on Windows because it uses the same system that OneDrive does, and is baked in to the OS. Not sure what the excuses are on MacOS and Linux.
But if you're using Dolphin or Nautilus on Linux, does setting up a WebDAV network location not meet your needs?
That would work fine for linux, but the folks who need to upload stuff to me server can't do that. They're running Macos which doesn't really support webdav well (and SMB is a mess too), plus they're on an external network and I don't want to have to get them on my VPN