Hi @ByTheBeat, thanks so much for your post. That is a great question!
At the moment, there isn't a way to upload files directly onto your Square dashboard for download. Once your customers have purchased the digital item, the best way to get it to them would be to manually send it to them via email. This is a great idea though, and would definitely be useful for businesses that sell mostly digital items. I'll be sure to share your comment with our product team for their consideration.
Let me know if you need anything else!
