Josh said: Thank you both for replying! @timmaugh Yes its 100% web-hosted, currently it has no relation to roll20. The sendChat() you mentioned is what I am seeking. Unfortunately Oosh suggested it doesn't exist. Just to clarify this - sendChat() certainly does exist, it just isn't a public-facing API, it's a sandbox method limited to user-written sandbox scripts. You can use that instead of piggybacking the DOM to post something to chat, but that's only simplifying the easy part. You still need an active player inside the campaign to trigger the sandbox script to do the sendChat - that means you still need to solve the problem of your website communicating with the player in the game. If you want to use a single dummy account to roll every sheet, just create a second account and promote them to GM in the game - that gives them access to all character sheets automatically. As long as you create the game from your main Pro account, all Pro features would still work. Whether you go the sandbox/sendChat route (probably better since you have more options for the message format) or the DOM method to post to Roll20 chat, you still need a script or extension to either be listening for a postMessage, or open a websocket (or similar) back to your server - that's the complicated part, as you need to be able to push messages to your Roll20 listener account on demand. I don't think the message API works between separate instances of a browser- it's for popups & iframes to communicate with the main window. Likewise the tabs API is limited to the same instance of the browser. I haven't used either extensively, so it might be worth reading up on them. A websocket connection from the listener account to your server would be ideal, but is complex if you haven't delved into that before, and also depends on exactly what kind of web host you're using.