Preheat oven to 350°F. Spray a mini muffin pan with non-stick spray.

In a large bowl, mix cake mix, butter, and eggs until soft dough forms.

Scoop dough by rounded teaspoons into mini muffin wells (about 36 total), filling each about 2/3 full.

Bake for 9–10 minutes or until set. Cool in pan for 5 minutes.

Press the center of each cookie with a mini tart shaper or the end of a wooden spoon to form a well. Loosen edges with a butter knife and cool completely on a wire rack.

In a small bowl, whisk together milk and pudding mix; set aside to thicken.

In a separate bowl, beat 1 cup heavy cream to stiff peaks. Fold in the pudding mixture and beat until smooth. Transfer to a zip-top bag, snip the corner, and pipe cream into each cookie cup.

In a microwave-safe bowl, combine remaining ¼ cup cream and chocolate chips. Microwave in 15-second intervals, stirring in between, until melted and glossy.

Spoon chocolate over each cookie cup. Serve immediately or refrigerate up to 3 days.