Caramelized Oranges With Chocolate Shortbread and Caramel Ice Cream

Preparation

1. Step 1

   Place 1 cup of sugar in a medium saucepan and stir in water. Use a pastry brush dipped in water to wash down any sugar crystals on the side of the pan. Place over medium heat and cook without stirring until mixture turns a deep caramel color. Remove from heat and carefully add the milk and cream. Return to heat and stir until caramel is dissolved. Bring to a simmer. Meanwhile, whisk egg yolks and¼ cup of sugar together.

2. Step 2

   Whisking rapidly, add caramel mixture to yolks. Pour mixture back into pan and place over low heat. Stir constantly until thick enough to coat the back of a spoon, about 15 minutes; do not let it come to a simmer. Pour into a bowl, cool and refrigerate until cold. Stir in vanilla. Freeze in an ice-cream machine.

3. Step 3

   Meanwhile, preheat oven to 350 degrees. Place flour, confectioners' sugar, salt and cocoa into a food processor and pulse. Add egg and pulse until mixture just begins to come together. Press dough together and on a floured surface roll to a thickness of ¼ inch. Cut into rounds using a 2-inch cookie cutter. Gather and reroll scraps until all the dough is used. Place on parchment-lined baking sheets and bake until set, about 20 to 25 minutes. Cool.

4. Step 4

   Preheat broiler. Place orange sections in a baking dish in a single layer and sprinkle with sugar. Broil until sugar browns, about 4 minutes. Place a scoop of ice cream in 6 dishes. Top with oranges and serve with shortbread.