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Step 1
Preheat the oven to 350°F. Place seven 1 cup ramekins or pudding cups on a rimmed half sheet baking pan. Set aside.
Step 2
Unwrap all of the caramels and set aside. If they are warm and difficult to unwrap, place in the freezer for about 5 minutes. Set aside in a single layer.
Step 3
Whisk together in a medium bowl half the granulated sugar 3/4 cup (150 grams), the flour, half the cocoa, 1/4 cup cocoa (25 grams), baking soda and salt. Set aside.
Step 4
In a second bowl, whisk together the remaining 1/2 cup granulated sugar (100 grams), the remaining 1/4 cup cocoa (25 grams) and the brown sugar. Make sure the cocoa is mixed in completely. Set aside.
Step 5
In a 1 cup container, microwave the milk and butter just to melt the butter. Cool to lukewarm if necessary. Add the vanilla and whisk together. Pour this over the flour mixture and whisk to make a smooth batter.
Step 6
Place 1/3 cup batter in each ramekin. Alternatively, spread all of the batter into a 9" pie pan.
Step 7
Spoon 2 tablespoons +1 teaspoon of the brown sugar mixture into each other the ramekins over the batter. Alternatively add all of the brown sugar mixture of the batter in the 9" pie pan. Shake the ramekins or pie plate to even out the dry ingredients.
Step 8
Place 4 caramels in each ramekin or all of them in the 9" pie plate on top of the dry ingredients.
Step 9
Boil 1 1/4 cup water. Spoon 2 tablespoons +1 teaspoon over the caramels in the ramekins or all of it over in the pie pan.
Step 10
Bake for about 17 to 19 minutes just until the brownie is set around the edges but the middle is still wiggly. Do not over bake or there won't be any fudge sauce. The 9" pie pan may take longer.
Step 11
Cool about 20 or 30 minutes. Serve with a scoop of vanilla ice cream and top with a cherry.