Pidgeot: There is definitely something wrong with that image, because all of that bonus content is supposed to have a little icon next to it. I'm guessing the two issues are related.
I don't have a pending update waiting at the moment, so I can't show you the exact indicator, but I've attached an image with the kind of thing I see for my downloads.
I'm also using a different browser (IE), so that may also be part of the problem.
You'd not want to see my screenshot of that same content :-P
The image I posted is using Pale Moon (a Firefox fork) where I have the NoScript and RequestPolicy add-ons installed and block Google, GoogleUserContent, Google-Analytics, Facebook and Twitter javascripts and cross-site requests by default. So, unless the "NEW" logo and those little icons in your screenshot are hosted on any of these sites, they should be showing for me.
But now the question is - why does the general update flag show and the item-specific one doesn't? Are they not hosted on the same site?
EDIT: Ok, those little icons show in Sware Iron (a Chrome fork) which has pretty much the same settings with Pale Moon, but don't show in Firefox with none of the above restricting settings. So, maybe it's a Firefox related bug?
I can't test IE as I've got javascript issues with it and no Flash Player installed - but even if I could and it worked, I'd never use it as I deeply dislike that browser.