I have made a lot of ruffled milk pies in my time, but this apple butter version is probably our very favorite of them all. The combination of our favorite fall flavors with one of our most beloved Greek pastries is perfectly meant to be. The fact that this ruffled milk pie is one of the simplest pastries to put together makes it all the more wonderful!
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Add Apple (3 pound) pieces to a pot along with Water (1 cup) (or apple cider), Granulated Sugar (1/3 cup), Cinnamon Stick (1), and Star Anise (3).
Bring to a simmer over medium-high heat, then reduce the heat to medium-low. Cover and cook the apples for 20 to 25 minutes or until the apples begin to soften and fall apart.
Remove from heat and process the softened apples with a blender, food processor, or hand blender until smooth. You should end up with about 4 cups of apple puree.
Return the puree to the pot and set over medium-low heat. Add Brown Sugar (1/2 cup), Ground Cinnamon (1 teaspoon), Ground Cloves (1/4 teaspoon), and Salt (1 pinch). Stir well to combine.
Gently simmer the puree, stirring regularly to avoid spattering, until the apple butter is deep caramel in color and thick enough to hold its shape on a spoon. This usually takes an additional 30 minutes.
Transfer the apple butter to jars or airtight containers and allow to completely cool. Apple butter will keep in the refrigerator for up to 3 weeks.
Preheat your oven to 350 degrees F (175 degrees C). Brush two 9-inch round cake pans lightly with melted butter and line each pan with a round sheet of parchment that is large enough just to come up the sides of the baking pan. Lightly brush the parchment with butter.
Place 1 sheet of Phyllo Dough (14 sheet) on a clean surface and brush it with Unsalted Butter (12 tablespoon). Place another sheet of phyllo over the top of the first one and brush with butter. Use your fingers to scrunch up the phyllo long ways, into a loose ruffled strip (it's okay if the phyllo tears a bit).
Wind up the dough into a loose, ruffled spiral, place it in your prepared pan. Repeat this process with the rest of the phyllo dough, placing each additional ruffled set of phyllo around the initial spiral to create a large rosette (you should need about 7-8 sets of ruffled phyllo to loosely fill the pan)
Brush the tops of the ruffled phyllo generously with the remaining butter. Bake in preheated oven for 20-25 minutes, until the phyllo is golden brown.
While the phyllo bakes, prepare the apple butter custard by whisking together the Milk (2 cup), Apple Cider (1 cup), Corn Starch (3 tablespoon), 2 cups of apple butter, Vanilla Extract (2 teaspoon), and Brown Sugar (1/2 cup).
Remove the pans from the oven and pour the apple butter custard mixture over the spirals. Return pans to the oven and bake another 20-25 minutes or until the custard is set in the center.
Let the pies cool in the pans for about 10 minutes and serve slices dusted with Ground Cinnamon (1/2 teaspoon) and Powdered Confectioners Sugar (1 tablespoon). Best eaten warm, but leftovers store beautifully in the fridge for up to 3 days (if it even lasts that long). Reheat leftovers for the best experience.