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Preheat your oven to 350°F (175°C) and grease a mini muffin pan well.
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Cream the butter and sugar together until light and fluffy.
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Beat in the egg and vanilla extract until fully combined.
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In a separate bowl, whisk together the flour, baking powder, and salt.
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Gradually mix the dry ingredients into the wet mixture until combined.
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Scoop the dough into the mini muffin pan, filling each cavity about halfway.
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Bake for 10–12 minutes until lightly golden.
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While warm, gently press the center of each cookie to form a cup. Let cool completely.
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Fold the whipped topping into the vanilla pudding until smooth.
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Spoon or pipe the cream filling into each cooled cookie cup.
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Heat the chocolate chips and heavy cream until smooth and glossy.
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Spoon the chocolate topping over the filled cookie bites and chill for 20–30 minutes before serving.