We’ve implemented “twitter cards” which allows twitter to display an image/context whenever one of our urls is shown on the main site. It appears that the card data is not sent to their api yet, so this isn’t working in non-official twitter clients. But I would expect that they will open this up soon.
Example of drilling down on the details for a tweet below.
And this is what happens when you click “view picture” in your feed (not much different than the other image).