Apple Jack Stack Cake
['3 pounds assorted apples, peeled and cut into 1/2-inch wedges', '1/2 cup brown sugar', '1 cup apple cider', '1/4 cup applejack, apple brandy, or bourbon', '1 1/2 cups apple butter', '5 cups all-purpose flour', '1 teaspoon baking powder', '1 teaspoon baking soda', '1/4 teaspoon kosher salt', '1/3 cup buttermilk', '1 teaspoon vanilla extract', '3/4 cup (1 1/2 sticks) unsalted butter', '2 cups granulated sugar', '1/4 cup molasses', '2 large eggs', '1 cup dark brown sugar', '1/4 cup reserved apple cider mixture (from the filling)', '1 tablespoon molasses', '2 tablespoons unsalted butter']
Put the apples, brown sugar, cider, and applejack in a large saucepan; bring to a boil over medium-high heat. Reduce the heat to medium-low and simmer, covered, stirring occasionally, until the apples are tender, about 20 minutes. Drain the apples and reserve 1/4 cup of the liquid. Set aside.
Position the racks in the upper-middle and lower-middle of the oven and preheat the oven to 350°F. Coat two baking sheets with cooking spray.
In a medium bowl, whisk the flour, baking powder, baking soda, and salt together. In a large liquid measuring cup, whisk together the buttermilk and vanilla.
In large bowl, with an electric mixer at medium-high speed, beat the butter and granulated sugar until light and fluffy, about 2 minutes. Reduce the speed to medium-low and add the molasses, beating until incorporated. Add the eggs one at a time and mix until incorporated. Gradually add the buttermilk (the mixture will look curdled); add the flour mixture and mix until a soft dough forms—it should look like cookie dough. Remove the dough from the bowl, pat into a round, cover in plastic wrap, and refrigerate for 20 minutes.
Divide the dough into 6 equal portions, about 8 1/2 ounces each. On parchment paper, roll portions of dough into circles about 1/4 inch thick. Use an 8-inch cake pan as a guide to trim into uniform 8-inch circles. Bake one circle on each prepared sheet until golden brown, 10 to 12 minutes, rotating and switching the baking sheets halfway through baking. Transfer the circles to cooling racks and let cool completely. The cakes will harden and set as they cool. Repeat with remaining dough. Reroll scraps to form a seventh layer.
Place the first layer on a serving plate and spread with 1/4 cup of the apple butter. Arrange one-sixth of the cooled cooked apples on top of apple butter and top with another layer of cake. Repeat with the remaining filling and cake layers, ending with a cake layer on top. Wrap the cake tightly in plastic wrap and refrigerate until the layers soften, at least 12 hours and up to 2 days.
In a small saucepan, combine the brown sugar, reserved apple cider mixture, and the molasses. Bring to a low boil over medium-high heat and cook until the sugar is dissolved, about 2 minutes. Remove from the heat and stir in the butter until smooth. Let cool for 5 minutes, then pour the glaze over the top of the cake. Slice and serve, or store the cake, covered, at room temperature for up to 3 days.
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