Preheat your oven to 350°F (175°C). Line the bottom of a 9-inch round cake pan with parchment paper and grease the sides with 2 tablespoons of unsalted butter.
In a medium saucepan, melt the butter over medium heat until bubbly. Stir in ½ cup granulated sugar and cook until it starts to caramelize. Add the cherries and cook for another few minutes. Stir in 1 teaspoon of vanilla extract and remove from heat.
Pour the warm cherry mixture into the prepared cake pan, distributing the cherries evenly over the bottom.
In a large mixing bowl, sift together the dry ingredients: flour, 1 cup granulated sugar, cocoa powder, baking powder, baking soda, and salt.
In another bowl, whisk together the wet ingredients: eggs, buttermilk, vegetable oil, and vanilla extract until smooth.
Gradually add the wet mixture to the dry ingredients, stirring gently until just combined. Stir in boiling water until the batter is smooth.
Carefully pour the chocolate batter over the cherry topping in the cake pan, ensuring it spreads evenly.
Place the cake pan in the preheated oven and bake for 35-40 minutes. Check with a toothpick for doneness.
Remove the cake from the oven and let it cool in the pan for about 10 minutes. Carefully turn the cake upside down on your serving dish.
Notes
For the best flavor, use fresh cherries when possible. Serve warm for the best taste experience.