Whisk in the cocoa and vanilla. Steep for one hour.
Whisk together egg yolks in separate bowl. Rewarm milk mixture and while whisking egg yolks add ½ cup of warmed milk, continuing to whisk. Scrap egg and milk mixture back into sauce pan. Continue to stir and heat egg and milk mixture until it is well thickened, and can coat the back of a spoon.
Place chopped chocolate in bowl. and pass custard through a strainer into the chocolate.
Let sit for a minute so the chocolate melts. Stir until smooth. Refrigerate overnight.
The next day, stir in the bourbon. Churn according to manufacturers instructions. Once ice cream is formed, working in batches transfer ¼ of the mixture to a loaf pan (or whatever you plan on storing it in). Drizzle caramel sauce over top. Transfer in ¼ more, drizzle caramel sauce. Continue to do this until all ice cream is in storage container. Finish with a large drizzle of caramel. Freeze and eat!
Recipe by Talia Bunting at https://www.taliabunting.com/chocolate-bourbon-caramel-ice-cream/