@jellycrystals May be I am missing something, but the most straightforward approach I can think of is logging into your kid's iCloud Drive from your Windows browser (via icloud.com) and uploading files.
@ravigupta His school is a Google school and it all backs up on there I think. I just wanted to throw a few movies on it for a train ride to cover no wifi times. I will have a look into it. Thanks for the suggestion 🤘
@jellycrystals Documents by Readdle also helps you add files through a variety of mechanisms like smb shares.
And if it is just about videos, you can install a Plex server on one of the computers that is always on, and then everyone in the family can access it from any device.
@ravigupta Ooh! This looks promising! Thank you 👌