I'm working on a script implementation of the 5e mass combat rules from Unearthed Arcana. My script generates a custom HTML string with inline rolls, but then I pass it through a callback to evaluate those rolls. Can I get the inline roll output tooltip back into the HTML without re-rolling? If the output is initially already in the desired form, and you don't need to process it further depending on the results of the inline rolls, you might consider not using a callback, but sending it to chat normally and then listening to the result of your script-sent chat message (chat messages sent by scripts do generate chat:message events in the API). If you do need to change the output depending on the content of the rolls, you will have to do what Stephen suggested. If you want to take a look at my (terrible) code, I have an example of a function trying to faithfully recreate the inline rool including tooltip as part of GroupCheck (I leave out the yellow background, but that's easy enough to add).