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