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1
Preheat the oven to 450 degrees.
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2
On a metal baking sheet, roast the squash until its flesh is tender and collapsingabout 1/2 hour.
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3
Remove the squash from the oven and permit it to cool until you can comfortably scrape the flesh from its shell.
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4
Set the flesh aside.
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5
Over a gentle flame, heat the sugar in a large saute pan, stirring constantly, until it takes on a very dark, golden color.
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6
Add the squash and roll it around in the caramel.
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7
Because the squash will be colder than the caramel, the caramel will seize and harden, but after a moment or two over the gentle flame, it will melt.
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8
Add 2 tablespoons of the butter and the rum, combining the components well.
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9
Turn out the squash mixture into a bowl to cool thoroughly.
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10
Meanwhile, butter a 10-inch tart pan with a removable bottom and line it with the pastry, covering the pastry-lined pan with plastic wrap and placing it in the freezer for 20 minutes or in the refrigerator for 1 hour.
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11
Preheat the oven to 400 degrees.
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12
Coarsely chop the extra-bittersweet chocolate and combine it with the squash mixture.
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13
Spread the squash/chocolate mixture over the well-chilled, unbaked pastry and bake the tart for 15 minutes.
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14
Lower the temperature to 350 degrees and bake the tart for an additional 25 minutes or until the pastry is deeply golden.
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15
Permit the tart to cool a bit on a rack, then dust it with confectioners sugar and present it, very warm, with unsweetened, barely whipped cream or a bowlful of mascarpone, should you wish.
