Ok here is the situation that I faced a few weeks ago.
Someone downloaded my lead-magnet twice in a row and they did not receive the email containing the download link the second time around.
After speaking with support, I learned that the automation will not fire off an email if it has been previously triggered - this is bad news for the folks who downloaded your lead-magnet a while ago and need to download it again later for whatever reason.
Naturally, I had to find a workaround, and I did *big huge "proud of myself" grin*
Watch this video I made of the workaround so you can do it yourself.