Transferring multiple files doesn't work at the moment and it might be a good idea to show some warning instead of simply transferring the first file. I'll add a ticket for that. To be honest I'm not sure how transferring multiple files would work and I'm not sure if it's possible to save whole directories to disk from HTML5 filesystem, so for now it's going to be limited to one file only.
Error handling is a bit rough at the moment. It looks like the data channel was disconnected after transferring file info. Could you try again, or does it always happen for you? If it does happen always, could you report it at
https://github.com/cowbell/sharedrop/issues and specify browsers' names and versions and some info about the file (name, size, type) to help me reproduce it?
We managed to transfer 1.5GB file (between Chrome browsers, in Firefox it probably wouldn't work), but it looks like people get max transfer speeds of ~1MB/s at the moment, so it does take ages to transfer larger files - it would probably be faster to go out, buy a flash drive and copy the file using it instead :) Max file size is restricted by the size of temporary filesystem, which on my computer is about ~4GB. The app doesn't check yet if the transferred file is bigger than that, but we plan on adding it.