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Preheat oven to 350 and line a baking sheet with parchment paper.
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With a mixer, beat butter and sugar until light and fluffy. Add in the egg and vanilla. Beat.
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Once mixed, in a small bowl, sift cocoa powder, flour, espresso powder, baking soda, baking powder, and salt together. Slowly add dry ingredients into the wet. Mix until combined.
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Add in milk and mix until combined. The dough will be thick.***
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Roll dough into 1-2 Tbsp sized balls (depending upon how big of cookies you want). Once on the cookie sheet, press your thumb into the center of the cookie (the edges will crack slightly).
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Bake cookies for 10-11 minutes.
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Place caramels and cream in a microwave safe bowl. Heat mixture in microwave on HIGH power in 30 second intervals, stirring after each interval until melted and smooth. Spoon caramel into indentation in cookies.
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Next, with a double broiler (or microwave), melt chocolate chips.
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Once melted, spoon a little bit of the melted chocolate onto each cookie. If you want to add any chocolate drizzles, put some chocolate in either a piping bag or a small sandwich bag with the tip cut off and drizzle over cookies.
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Add toppings to your liking. Allow chocolate to set, about 30-60 minutes at room temperature.
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Enjoy with milk!