Preheat oven to 350°F and line a baking sheet with parchment paper.
In a large bowl, combine butter, granulated sugar, and brown sugar.
1/2 cup unsalted butter, 3/4 cup granulated sugar, 3/4 cup brown sugar
Beat in eggs one at a time and add vanilla.
2 eggs, 2 tsp pure vanilla extract
In a small bowl, combine flour, cocoa powder, baking powder, and salt.
2 1/2 cups unbleached flour, 1/2 cup unsweetened cocoa powder, 1 1/2 tsp baking powder, 1/2 tsp salt
Mix the dry ingredients into the wet ingredients. Dough will be thick and crumbly. You may have to use your hands to get it to come together.
Fold in mini chocolate chips.
1 cup semi-sweet mini chocolate chips
Using a 1 tablespoon cookie scoop, create cookie balls and place them 1" apart on the baking sheet.
Using the end of a large baking spoon or spatula, create a hole in the middle of each cookie then put pie filling in each hole and top with a cherry.
10 oz cherry pie filling
Bake for 10 - 11 minutes, until cookies look set. They will continue cooking on the baking sheet. Do not overbake!
Remove from oven and let cool on baking sheet for 10 minutes.
While cookies are cooling, melt almond bark in a microwave safe bowl in 20 - 30 second increments, stirring each time until melted. Then drizzle melted chocolate over cookies.
6 oz chocolate almond bark
Transfer cookies to cooling rack and let cool completely before serving.
Notes
Sprinkle cookies with white granulated sugar or decorator’s sugar immediately after taking them out of the oven to create a glassy/sparkly effect.Add about 1/8 teaspoon of coconut oil to your almond bark to make it smooth for drizzling so it doesn’t harden as quickly if you want to make it a little further in advance or if you’re worried about being interrupted and the chocolate melting before you have time to drizzle.You can transfer the almond bark to a zippered bag and cut the tip off the end for easy, mess-free drizzling. Use my viral TikTok trick to fill your bag!Store cookies in an airtight container for up to five days before either throwing away or freezing.Freeze these cookies by wrapping them individually in plastic wrap so the cherry filing doesn’t fall out in your container. Once wrapped, place in an airtight container in the freezer for up to three months.