Have all your ingredients measured out and ready to go.
Make the caramel. Combine the sugar and water in a heavy bottomed saucepan or Dutch oven. (Avoid pans with dark bottoms otherwise it will be hard to see how much caramel has cooked.) Cook over medium heat, without stirring, until the sugar has totally melted and is beginning to turn light amber. If the sugar crystals, don’t panic, just allow it to keep cooking and it will melt again.
Once the mixture is a deep amber color and just starting to let off wisps of smoke, remove from the heat and pour in the heavy cream all at once, stir vigorously with a whisk, then pour in the milk. Scrape the bottom of the pan to loosen up any seized caramel — it will melt into the mixture. Whisk in the salt and vanilla and return to the stove over medium-high heat. Bring the mixture to a boil and then immediately turn down to medium-low heat. Add in the rice.
Cook the rice at a simmer for about 35 to 45 minutes, stirring and scraping the bottom of the pan regularly, especially towards the beginning. Continue cooking until the pudding has thickened, the milk has been absorbed, and most importantly, the rice is tender with just a bit of chew in the middle. Pour the pudding into four to six individual serving vessels, or a large bowl, and set aside while you make the chocolate ganache. If you’re not making the ganache, press some plastic wrap directly onto the surface of each pudding to prevent them forming a skin, and then chill them in the refrigerator before serving, about one to two hours.
For the chocolate ganache, place the finely chopped chocolate in a small, heat-safe bowl. Heat the cream over the stove or in the microwave until it is just barely simmering, then pour it over the chocolate and cover the bowl for about 30 seconds. Stir together the chocolate and cream just until homogenous. Pour the ganache in a thin layer on top of each pudding, gently jostling them to level out the chocolate. Chill the puddings in the refrigerator to cool and set completely before serving, about one to two hours. Sprinkle with flakey salt, if desired, and serve!