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Ingredients
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Crust
Ham, Bacon & Pineapple Filling
Optional Garnish
Method
Crust
Make dough
In a large bowl whisk together 2.25 cups all-purpose flour, 1 tsp sugar, and 3/4 tsp fine sea salt. Add 1 cup (2 sticks) cold unsalted butter cubes and, using a pastry cutter or two forks, cut the butter into the flour until mixture resembles coarse crumbs with some pea-sized pieces.
Add water
Sprinkle 6 tablespoons cold water over the flour-butter mixture a tablespoon at a time, gently tossing with a fork after each addition until dough just holds together when pressed. Do not overwork.
Chill and roll
Turn dough onto a lightly floured surface, gather into a disk, wrap in plastic, and chill in refrigerator for at least 30 minutes. For a 28" pie (very large), you will need to double this crust recipe to have top and bottom crusts; scale quantities accordingly. After chilling, divide dough for bottom and top crusts if needed, roll out on a floured surface to a circle large enough to line the pie pan and cover it. Transfer bottom crust to the pie pan, trim and reserve the excess for fluting or lattice.
Ham, Bacon & Pineapple Filling
Cook bacon
Preheat oven to 375°F (190°C). In a large skillet over medium heat, cook 16 slices thick-cut bacon until crisp, about 8–10 minutes, turning as needed. Remove bacon to a paper towel-lined plate to drain; when cool, chop into 1/2" pieces. Reserve 1–2 tablespoons bacon fat in the skillet and discard the rest (or save for other uses).
Sauté aromatics
Add 2 tablespoons unsalted butter to the skillet with reserved bacon fat over medium heat. Add 1 cup finely chopped onion and cook until translucent, about 4–5 minutes. Add 3 teaspoons minced garlic and cook another 30–60 seconds until fragrant.
Make roux
Sprinkle 4 tablespoons all-purpose flour over the softened onion mixture and cook, stirring constantly, 1–2 minutes to remove raw flour taste.
Add dairy and thicken
Slowly whisk in 2 cups whole milk, bringing mixture to a simmer. Simmer until sauce thickens and coats the back of a spoon, about 3–5 minutes. Whisk in 4 ounces softened cream cheese until smooth to create a creamy binder.
Season and combine
Stir in 2 tablespoons light brown sugar, 1 tablespoon Dijon mustard, 1 tablespoon fresh thyme leaves, 1 teaspoon black pepper, and 1 teaspoon kosher salt. Taste and adjust seasoning. Fold in 6 cups diced cooked ham, chopped bacon, and 4 cups pineapple chunks until evenly coated with the sauce.
Cool filling
Remove the filling from heat and let it cool for 10–15 minutes so it thickens further and will not overly soften the crust when assembled.
Assemble & Bake
Fill pie
Preheat oven to 400°F (205°C) if not already hot. Line the pie pan with the prepared bottom crust (see note about doubling for 28"). Spoon the cooled ham, bacon & pineapple filling into the crust, mounding slightly but leaving about 1/2" clearance to the rim for the top crust.
Top crust and finish
Roll out the top crust and place over the filling. Trim excess dough, press and flute edges to seal. Cut a few vents in the top to allow steam to escape, or create a lattice top. Whisk 1 beaten egg with 1 tablespoon milk and brush the pastry with egg wash for a golden finish.
Bake
Bake at 400°F (205°C) for 20 minutes to set the crust, then reduce oven temperature to 350°F (175°C) and continue baking until crust is deep golden and filling is bubbling, about 40–55 minutes more (total bake time ~60–75 minutes depending on pan depth and exact size). If edges brown too quickly, shield them with foil after 30 minutes of baking.
Rest before serving
Remove pie from oven and let rest on a wire rack 20–30 minutes to allow filling to set. This makes slicing cleaner and helps internal temperature settle.
Garnish and serve
Sprinkle with 2 tablespoons chopped fresh parsley and garnish with thyme sprigs if desired. Slice and serve warm.