Without the API, it isn't possible as far as I know. If all you want is the picture, then Silvyre came up with a slick workaround a while back (can't find the exact post now). Find the html address of the picture you want (you can do this by right clicking an image in your library and opening it in a new window. Make sure to change the "thumb" part of the image url to "max" and remove the "?##########" that comes after the image tag. Example url before modifications: <a href="https://s3.amazonaws.com/files.d20.io/images/23613384/NPlJmQNuO6JsRvvAc53ddQ/thumb.png?1475105831" rel="nofollow">https://s3.amazonaws.com/files.d20.io/images/23613384/NPlJmQNuO6JsRvvAc53ddQ/thumb.png?1475105831</a> After Modifications: <a href="https://s3.amazonaws.com/files.d20.io/images/23613384/NPlJmQNuO6JsRvvAc53ddQ/max.png" rel="nofollow">https://s3.amazonaws.com/files.d20.io/images/23613384/NPlJmQNuO6JsRvvAc53ddQ/max.png</a> Now go to tinyURL . Copy your modified picture URL into the "enter url" text box there and use the custom alias option to make your address for each picture have a number somewhere in it (same place for all pictures for a given table. And make sure it ends in an image tag (.jpg, .png, or .gif). Now to display the image in chat use the embed html link syntax for chat: [Text to display](URL) In this syntax, if the url ends in an image tag, it will display the image instead of the text that is between the square brackets. To mimic a rollable table, you will do: [Text to display, doesn't matter for image]( <a href="http://tinyurl.com/ImageTable[[1d6]].jpg" rel="nofollow">http://tinyurl.com/ImageTable[[1d6]].jpg</a> ] The inline roll is resolved prior to the link, and so you should be able to get random images to show up. It's a lot of setup, but I think it is the only way to do what you are asking for, hope it helps Scott EDIT: Gah, nvm, tinyurl doesn't play well with image tags at the end of their made addresses. If you can find a shortening service that does allow it, then the above would work. EDIT the Second: Found the thread with Silvyre's post in it . This apparently only works if you embed it in an API Command Button (does not require API or Pro Membership). Instead of making the tinyUrl have the image tag on it, you make the tinyUrl without the image tag. then when you enter it in the embed link syntax you add a fragment onto the end with the image tag: [Generate](!&#13; &amp;#1; [White Wraith]( <a href="http://tinyurl.com/testerimage[[" rel="nofollow">http://tinyurl.com/testerimage[[</a> [[1d1]] ]]#.png&#41;) Maybe Silvyre will stop by and explain why it requires the API command button ( or more likely one of those html replacements is required to make it work; my money's on the &amp;#1; ) and if there is a way to get it to work outside of them.