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1
Preheat oven to 350F.
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2
Stir 1/2 cup sugar and 1/2 cup water in heavy small saucepan over low heat until sugar dissolves.
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3
Increase heat; boil without stirring until deep amber color, brushing down sides of pan with wet pastry brush and swirling pan occasionally, about 5 minutes.
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4
Carefully pour caramel into 5-cup ring mold.
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5
Using pastry brush, quickly brush caramel up sides of mold.
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6
Cool.
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7
Whisk 1 cup milk and cocoa in large bowl until cocoa dissolves.
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8
Whisk in remaining 2 cups milk, 2/3 cup sugar, rum, egg yolks and eggs.
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9
Stir in amaretti cookies.
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10
Pour custard into caramel-lined mold.
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11
Place mold in large roasting pan.
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12
Add enough warm water to roasting pan to come halfway up sides of mold.
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13
Cover pan and ring mold with foil and bake 20 minutes.
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14
Remove foil and bake until crust forms on top of custard and center 1 inch still moves when mold is gently shaken, about 35 minutes (do not overbake or custard will curdle).
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15
Transfer mold to rack and cool completely.
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16
Cover and chill overnight.
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17
Using small sharp knife, cut oranges between membranes to release segments.
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18
Run knife around sides of mold.
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19
Place plate atop mold.
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20
Invert custard onto plate, shaking gently to loosen and letting caramel run over custard.
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21
Remove mold.
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22
Arrange fruit in center of custard.
