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1. 1
   Place one 14-oz. can sweetened condensed milk, unopened, label removed, on its side in a large pot; pour in room-temperature water to cover by at least 2". Bring to a simmer over medium-high heat. Reduce heat to low, partially cover, and simmer, adding water as needed to maintain level, for 3 hours. Let cool in water in pot, 40–60 minutes. Remove can from pot and chill at least 12 hours before opening.
2. 2
   Combine 3 cups (375 g) all-purpose flour, 1 Tbsp. granulated sugar, and 1 tsp. Diamond Crystal or ½ tsp. Morton kosher salt in a large wide bowl. Toss in 1 cup (2 sticks) chilled unsalted butter, cut into ½" pieces, until generously coated. Using your fingers, smash butter into thin disks, tossing with flour as you go. Work until all of the butter has been smashed and coated (irregular pieces of butter produce a flakier crust). Sprinkle over 2 Tbsp. apple cider vinegar and 1 Tbsp. ice water and toss with a wooden spoon until just combined (the spoon prevents the butter from warming too quickly). Add another 3 Tbsp. ice water a tablespoonful at a time, stirring after each addition until water is absorbed. Using your hands, continue to work in water by the tablespoonful just until mixture holds together when squeezed in your hand, 2–4 Tbsp. more.
3. 3
   Turn mixture out onto a lightly floured work surface and gently knead until a dough forms (be careful not to overwork). If dough is too dry, sprinkle with a few drops of water; if too sticky, work in a little more flour. Roll dough to about an 8x5" rectangle, then fold in half crosswise. Roll back out to an 8x5" rectangle, dusting surface as needed, and fold again. Repeat rolling and folding 2 more times. Divide dough in half. Tightly wrap each half in plastic wrap or parchment paper and gently form into 1"-thick disks (you’ll only need 1 for the tart). Chill at least 1 hour.
4. 4
   Let 1 dough disk sit 5 minutes at room temperature. Line tart pan with parchment paper, leaving some overhang. Roll out dough on a lightly floured surface, rotating often and dusting as needed to prevent sticking, to ¼" thick. Fold dough in half and transfer to prepared pan. Unfold and lift edges so dough slumps down into corners. Gently press dough into pan with the back of your index finger. Trim pastry with kitchen shears or a paring knife to a 1" border (reserve dough scraps for tart crust decorations if desired). Fold excess over into pan and press double layer into sides of pan. Using a fork, prick bottom of tart a few times. Chill while you prepare the filling. Do Ahead: Unopened dulce de leche can be made 3 months ahead; keep chilled. Opened dulce de leche can be made 3 weeks ahead; transfer to an airtight container and chill. Dough can be made 3 days ahead; keep chilled, or freeze up to 3 months. Thaw at room temperature 1–2 hours or in the fridge overnight before using.
5. 5
   Place a rack in bottom third of oven; preheat to 375°. Pour ⅓ cup fresh lemon juice onto a large rimmed plate or into a shallow bowl. Hold stem of 1 of 3–4 pears (depending on their size; preferably Starkrimson or red Anjou) and cut vertically into 4 lobes, working your way around the core; discard core. Repeat with remaining pears. Arrange lobes cut side down and slice lengthwise ¼" thick, keeping slices in groups. Place in lemon juice to prevent cut sides from browning.
6. 6
   Combine 3 Tbsp. granulated sugar, 2 Tbsp. all-purpose flour, 1 Tbsp. finely grated lemon zest, ½ tsp. Diamond Crystal or ¼ tsp. Morton kosher salt, and ½ tsp. ground cinnamon in a small bowl. Sprinkle mixture evenly over dough and dot all over with 2 Tbsp. unsalted butter, cut into small pieces, frozen. Fan each group of pears in crust in alternating directions.
7. 7
   Whisk 1 large egg, a pinch of salt, and 1 Tbsp. water in a small bowl to combine. Brush edges of tart shell with egg wash and sprinkle 2–3 Tbsp. raw sugar in an even layer over pears and crust. Place tart on a rimmed baking sheet and bake until crust is golden brown and filling is bubbling slightly, about 1 hour. Transfer to a wire rack and let cool. Remove tart from pan by lifting parchment and transfer to a cutting board or large plate.
8. 8
   To serve, cut tart into slices and transfer to plates. Drizzle dulce de leche over each slice if desired. Do Ahead: Tart can be made 1 day ahead. Store lightly wrapped at room temperature. Editor’s note: This pear tart recipe was first printed in November 2020; it has been updated for style. Head this way for more of our favorite Christmas dessert recipes →