In large saucepan, melt the butter and mix in the sugar. Set aside to cool slightly, about 10 minutes.
After the mixture has cooled to a temperature that won’t cook the eggs, stir in the eggs and mix thoroughly.
Add the baking powder, baking soda, salt, vanilla and cocoa, stirring after each addition. Add the flour and mix well. The dough will be stiff and a bit crumbly.
Drain the cherries and reserve the juice (you will need some of the juice later).
Roll the dough into walnut-sized balls and place on a greased cookie sheet, 12 per sheet. I like to use a scoop for this so they’re all evenly sized.
Press down in the center of each ball to make a deep indentation. Place one cherry in each indentation.
Combine the chocolate chips and the sweetened condensed milk in a microwave-safe bowl. Heat them on HIGH for 1 minute. Stir. If the chips are not melted, process on HIGH in 10minute increments until they can be stirred smooth.
Add about 2 tablespoons of the reserved cherry juice to the melted chocolate mixture until the frosting is thick and will glob off a spoon. If it won’t glob off, keep adding juice until it is the right consistency.
Spoon a small bit of the frosting over the center of each cookie – just enough to cover the cherry. It shouldn’t drip down the sides.
Bake at 350°F in the preheated oven for 10 to 12 minutes.
Let the cookies cool on the baking sheet for 2 minutes, and then remove to a wire rack to cool completely.
Notes
This makes a pretty large batch but the recipe can be easily halved. These cookies also freeze well! Store in an airtight container and separate cookie layers with wax paper. Date and label the container and freeze for up to 3 months. NOTES: If you don’t like cherries, you can substitute well-drained pineapple tidbits, using the juice for the frosting. You can also use pecan halves or macadamina nuts and thin the frosting with cold coffee or water. If you don’t have anything to go on top, just use the frosting because that’s good too!