Remove ice cream from freezer and allow it to soften while you prepare the cookie dough and cupcake cups. Depending on the temperature in your kitchen, it will take 20 – 40 minutes for the ice cream to soften. It should be the consistency of very soft soft serve.

Cookie Dough:

Preheat oven to 350° F / 176° C. Line a small baking tray with parchment or a silicone mat.

Spread flour on prepared tray. Bake in preheated oven for 5 minutes, tossing periodically with a spatula. Allow to cool completely. (Note: Raw flour is not safe to eat. Heat-treating is important; this process kills bacteria and allows the flour to be consumed safely. Do not skip this step.)

In a small bowl, combine flour, brown sugar, granulated sugar, vanilla extract, butter, milk, and salt. Use your hands to knead the ingredients together.

Add the chocolate chips and knead until fully incorporated.

Pat cookie dough into a disc. Wrap in clingfilm/plastic wrap and place in the freezer until ready to use.

Chocolate Cups:

Arrange silicone cupcake liners on a small tray or plate. (Make sure it fits in your freezer!)

Melt dark chocolate over a bain marie or double boiler. (Alternately, you can melt the chocolate in the microwave.)

With a pastry brush, brush a thin layer of melted chocolate inside each of your silicone cupcake liners. Place liners in the freezer to chill briefly, about 3-5 minutes, or until solid.

Remove liners from freezer. Brush another layer of chocolate into each liner and return to freezer. Repeat this process until your chocolate has reached the desired thickness (I used three coats of chocolate for each cup.)

Remove liners from freezer and carefully “pop” the molded chocolate cups from the liners.

Assembly:

Line a small tray with parchment or a silicone mat. Place chocolate cups on the tray.

Transfer softened ice cream to a disposable piping bag.

Pipe a generous dollop inside each chocolate cup, filling the cups about halfway.

Spread with a small stepped palette knife (the back of a spoon or a tiny spatula will also work).

Top with a layer of crumbled cookie dough.

Pipe a second layer of vanilla ice cream on top of the cookie dough, and spread to distribute it evenly over the surface.

Freeze cupcakes for 30 minutes or until ready to serve.

Decoration:

Just before serving, pipe the tops of the cupcakes with swirls of whipped cream.

Decorate with sprinkles, pieces of crumbled cookie dough, or both.

Serve immediately.