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1
Preheat the oven to 350.
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2
In a small bowl, cover the prunes with the pisco and let stand for 1 hour, until plump.
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3
Meanwhile, bring a medium saucepan of water to a boil.
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4
Add the kabocha squash and simmer until tender, about 10 minutes.
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5
Drain well.
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6
Transfer the squash to a food processor and puree until smooth.
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7
Place the bread on a rimmed baking sheet; bake for 15 minutes, until just dry.
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8
In a large saucepan, combine the 3 milks with the brown sugar, anise seeds, cloves, cinnamon and allspice and bring just to a simmer, stirring until the sugar is dissolved, about 2 minutes.
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9
Whisk in the pureed squash.
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10
Strain the mixture through a fine-mesh sieve set over a large bowl; discard the solids.
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11
Whisk the butter, egg yolks and vanilla into the mixture and stir in the toasted bread cubes.
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12
Drain the prunes, pressing to extract as much of the soaking liquid as possible, then discard the liquid.
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13
Add the prunes to the bowl.
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14
Let the bread pudding mixture stand for 20 minutes, pressing to submerge the bread and stirring occasionally, until most of the liquid has been absorbed.
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15
Set a 9-by-13-inch baking dish near the stove.
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16
In a medium, heavy saucepan, combine the granulated sugar with 1/2 cup of the water and cook over high heat, stirring until the sugar is dissolved.
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17
Using a wet pastry brush, wash down the side of the pan to dissolve any crystals.
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18
Cook without stirring until a medium-amber caramel forms, about 8 minutes.
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19
Immediately pour half of the caramel into the baking dish, swirling it to coat the bottom.
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20
Return the saucepan to the heat and add the remaining 1/4 cup of water.
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21
Cook until the caramel liquefies, 2 to 3 minutes.
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22
Transfer the caramel sauce to a heatproof cup.
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23
Pour the bread mixture into the prepared baking dish and smooth the surface.
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24
Bake for about 40 minutes, until the pudding is set and lightly browned.
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25
Let cool for 20 minutes.
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26
Run a knife around the edge of the pudding, set a cutting board on top and invert.
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27
Remove the baking dish and cut the bread pudding into squares.
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28
Top with a dollop of creme fraiche, a drizzle of the caramel sauce and a sprinkling of cacao nibs.
