IF you look at the category listing, you'll see that there is no check on the "Send email to user on checkin/checkout" checkbox.
But when you click in to the Category, it looks like it's already checked (even though, in reality, it's not):
If you click 'Save' it will save the checkmark correctly however.
The way I'm thinking we should fix this is to make that field no longer 'disabled' when you type in a category-based EULA. I'm fine with default-checking it once a EULA has been input, but if it's not yet checked, we should show it that way. I think it should also be permissible to leave that box unchecked, which should make the EULA be sent on checkout, but not on checkin.