Caramelized Oranges With Chocolate Shortbread and Caramel Ice Cream

• 1 1/4 cups sugar
• 1/4 cup water
• 2 1/2 cups whole milk
• 1 1/2 cups heavy cream
• 6 egg yolks
• 2 teaspoons vanilla extract
• 2 cups all-purpose flour
• 1/2 cup confectioners' sugar
• 1/2 teaspoon kosher salt
• 6 tablespoons cocoa powder
• 1 egg, beaten
• 6 oranges, peeled, sections cut from between the membranes
• 6 tablespoons sugar

1. Place 1 cup of sugar in a medium saucepan and stir in water.
2. Use a pastry brush dipped in water to wash down any sugar crystals on the side of the pan.
3. Place over medium heat and cook without stirring until mixture turns a deep caramel color.
4. Remove from heat and carefully add the milk and cream.
5. Return to heat and stir until caramel is dissolved.
6. Bring to a simmer.
7. Meanwhile, whisk egg yolks and1/4 cup of sugar together.
8. Whisking rapidly, add caramel mixture to yolks.
9. Pour mixture back into pan and place over low heat.
10. Stir constantly until thick enough to coat the back of a spoon, about 15 minutes; do not let it come to a simmer.
11. Pour into a bowl, cool and refrigerate until cold.
12. Stir in vanilla.
13. Freeze in an ice-cream machine.
14. Meanwhile, preheat oven to 350 degrees.
15. Place flour, confectioners' sugar, salt and cocoa into a food processor and pulse.
16. Add egg and pulse until mixture just begins to come together.
17. Press dough together and on a floured surface roll to a thickness of 1/4 inch.
18. Cut into rounds using a 2-inch cookie cutter.
19. Gather and reroll scraps until all the dough is used.
20. Place on parchment-lined baking sheets and bake until set, about 20 to 25 minutes.
21. Cool.
22. Preheat broiler.
23. Place orange sections in a baking dish in a single layer and sprinkle with sugar.
24. Broil until sugar browns, about 4 minutes.
25. Place a scoop of ice cream in 6 dishes.
26. Top with oranges and serve with shortbread.

sugar, water, milk, heavy cream, egg yolks, vanilla, flour, sugar, kosher salt, cocoa powder, egg, oranges, sugar

Taken from cooking.nytimes.com/recipes/8353 (may not work)