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To make the dough: In the bowl of a stand mixer, whisk together the milk, egg, egg yolk, almond extract, sugar, salt, and zest.
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Add the flour and yeast to the bowl and, using the dough hook, mix at low speed until everything comes together, scraping the bottom and sides of the bowl to collect any stray flour. This should take about 2 to 3 minutes.
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With the mixer running add the butter in four additions, mixing until each is incorporated.
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Continue mixing at low speed until the dough pulls away from the bottom and sides of the bowl and is smooth and shiny, about 10 to 15 minutes. Cover the bowl with plastic wrap or a reusable cover and allow the dough to rise for about 90 minutes, or until it’s doubled in size.
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Gently deflate the dough and place it on a lightly floured or lightly greased work surface, or on a piece of lightly greased parchment. Roll it into a rough 10” x 15” rectangle. Transfer the dough (on its parchment) to a baking sheet; if you’re not using parchment, lightly grease the baking sheet.
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Using your fingertips, gently press and stretch the dough into a neat 10” x 15” rectangle. Cover with lightly greased plastic wrap or a reusable cover and let it rise for 30 minutes.
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While the cake is rising, preheat the oven to 350ºF.
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Sprinkle the cookie crumbs over the cake, then arrange the plum halves on the cake in 6 to 7 rows of 4 to 5 plum halves per row, flesh side up, pressing them in gently. In a small bowl, whisk together the sugar and cinnamon and sprinkle over the plums.
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Cover the cake and allow it to rise for 20 to 30 minutes.
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To make the topping: In a medium-sized bowl, whisk together the flour, sugars, and salt. Pour in the melted butter, first tossing with a spoon then working it in with your fingers until the mixture starts to become crumbly. Don’t mix too long; you don’t want it to become a cohesive mass.
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Sprinkle the topping over the cake. Place it in the oven and bake it for 30 to 40 minutes, until the edges are golden brown and the center registers 200°F to 205°F on a digital thermometer.
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Remove the cake from the oven and place it on a rack (still on its pan). Let it cool to lukewarm or room temperature before serving. Garnish each serving with whipped cream, if desired.
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Store any leftovers, well wrapped, at room temperature for a couple of days. Freeze for longer storage.