Preheat your oven to 350°F (175°C). Grease a 9-inch round cake pan and line with parchment paper.

In a medium saucepan over medium heat, melt 4 tablespoons of unsalted butter. Add 1 cup of granulated sugar, stirring constantly until it begins to bubble and caramelize.

Add 2 cups of tart cherries and 1 teaspoon of vanilla extract, cooking for another 2–3 minutes until cherries are slightly softened.

Pour the cherry mixture evenly into the prepared cake pan.

In a large mixing bowl, whisk together 1.5 cups of flour, 0.5 cups of cocoa powder, 2 teaspoons of baking powder, 1 teaspoon of baking soda, 0.5 teaspoon of salt, and 1 cup of granulated sugar.

In a separate bowl, mix 2 eggs, 1 cup of buttermilk, 0.5 cups of vegetable oil, and 2 teaspoons of vanilla extract until smooth.

Gradually add the wet ingredients to the dry ingredients, stirring until just combined. Slowly mix in 1 cup of boiling water.

Pour the chocolate batter over the cherry layer and bake for 35–40 minutes.

Allow the cake to cool in the pan for 10 minutes before inverting onto a serving plate.