Try loading a PDF into a handout, you get the following message: It looks like you're uploading a PDF. We'll convert it into an image for you, but we need to know what page you want to use (You can upload multiple times to do multiple images). If it's a single page PDF, just leave this set to 1. Now, I see how this can mean "You have to do a separate journal entry for each one." However, it doesn't say that, and it does imply at least that it can be multiple to one journal entry just uploaded multiple times. It probably should just be clarified.