Quick Recipe Version (TL;DR)
Quick Ingredients
- 1 (9-inch) single pie crust (homemade or refrigerated), chilled
- 6 tbsp (85 g) unsalted butter
- 3/4 cup (150 g) packed light brown sugar
- 1/4 tsp kosher salt
- 1 tbsp cornstarch + 1 tbsp pineapple juice (from the can)
- 1 (20 oz / 567 g) can pineapple rings in juice, well-drained (reserve 2 tbsp juice)
- 8–10 maraschino cherries, well-drained (optional)
- 1 tsp vanilla extract
- 1 large egg + 1 tbsp water (egg wash)
Do This
- 1) Heat oven to 375°F (190°C); place a rimmed sheet pan on the middle rack to preheat.
- 2) Melt butter; stir in brown sugar and salt; simmer 1 minute. Stir in cornstarch slurry; simmer 30 seconds. Remove from heat; stir in vanilla.
- 3) Pour caramel into a 9-inch pie plate. Arrange pineapple rings and cherries.
- 4) Roll crust to a 12-inch circle; lay over fruit; tuck edges down inside the pie plate; cut 5–6 vents.
- 5) Brush with egg wash; bake on preheated sheet pan 45–50 minutes until deep golden and bubbling.
- 6) Cool 15 minutes; run a knife around the edge; invert onto a serving plate.
- 7) Cool 20 minutes more to set; slice and serve (great with vanilla ice cream).
Why You’ll Love This Recipe
- All the upside-down flavor, in a pie. Buttery caramel soaks into pineapple, and the crust bakes crisp on top (then becomes the base).
- Sliceable and shareable. A little cornstarch helps the caramel set so you can cut neat wedges.
- Approachable technique. No complicated cake batter; it’s mostly assembly plus a simple stovetop caramel.
- Big nostalgia, fresh format. It tastes like the classic cake, but feels special and pie-shop worthy.
Grocery List
- Produce: (Optional) mint leaves or lemon for serving
- Dairy: unsalted butter, 1 large egg (optional: vanilla ice cream for serving)
- Pantry: light brown sugar, cornstarch, kosher salt, vanilla extract, canned pineapple rings in juice, (optional) maraschino cherries, all-purpose flour and sugar (if making homemade crust)
Full Ingredients
Option A: All-Butter Pie Crust (Recommended)
- 1 1/4 cups (150 g) all-purpose flour, plus more for rolling
- 1 tbsp (12 g) granulated sugar
- 1/2 tsp kosher salt
- 1/2 cup (113 g) unsalted butter, very cold, cut into 1/2-inch cubes
- 3 to 5 tbsp (45 to 75 ml) ice water
Option B: Store-Bought Shortcut
- 1 (9-inch) refrigerated single pie crust (usually 1 round from a 2-pack), kept chilled until using
Pineapple Upside-Down Filling (Caramel + Fruit)
- 1 (20 oz / 567 g) can pineapple rings in juice (not heavy syrup), drained very well
- 2 tbsp pineapple juice, reserved from the can (divided)
- 6 tbsp (85 g) unsalted butter
- 3/4 cup (150 g) packed light brown sugar
- 1/4 tsp kosher salt
- 1 tbsp (8 g) cornstarch
- 1 tsp vanilla extract
- 8–10 maraschino cherries, drained very well (optional, but classic)
For Finishing
- 1 large egg
- 1 tbsp water
- Optional for serving: vanilla ice cream, lightly sweetened whipped cream, or a few mint leaves
Step-by-Step Instructions
Step 1: Make and chill the crust (or prep store-bought)
If making homemade crust: In a medium bowl, whisk together the flour, sugar, and salt. Add the cold butter and cut it in using a pastry cutter (or pinch with fingertips) until you have a mix of pea-sized and almond-sized pieces.
Drizzle in 3 tbsp (45 ml) ice water and stir with a fork until the dough just starts to clump. Add more ice water, 1 tbsp at a time, only as needed. Turn the dough onto the counter and press into a disk (do not over-knead). Wrap tightly and chill for at least 30 minutes (and up to 2 days).
If using a refrigerated crust: keep it chilled until you’re ready to roll so it stays easy to handle.
Step 2: Preheat the oven and set up for no-drip baking
Place a rimmed sheet pan on the middle rack (this catches any caramel drips and helps the pie bake evenly). Preheat the oven to 375°F (190°C).
Have ready: a 9-inch pie plate (glass or metal both work), a large serving plate or platter for flipping, and a thin knife or small offset spatula for loosening the edges.
Step 3: Drain the pineapple thoroughly
Drain the pineapple rings very well, then gently press them between paper towels. This step helps prevent a watery filling and helps the caramel set up for clean slices.
Reserve 2 tbsp of pineapple juice from the can. You’ll use 1 tbsp to make a cornstarch slurry and keep the caramel glossy and sliceable.
Step 4: Cook the brown sugar caramel
In a small saucepan over medium heat, melt the butter. Add the brown sugar and salt and stir until the mixture looks smooth and starts to bubble. Let it simmer, stirring constantly, for 1 minute.
In a small bowl, whisk together the cornstarch and 1 tbsp reserved pineapple juice until smooth (no lumps). Pour the slurry into the bubbling caramel while stirring. Simmer for 30 seconds, stirring, until slightly thickened.
Remove from the heat and stir in the vanilla extract.
Step 5: Build the upside-down base (caramel, then pineapple)
Pour the hot caramel into the bottom of the 9-inch pie plate and tilt gently to coat the base evenly.
Arrange the pineapple rings in a single layer over the caramel. If you have extra rings, you can overlap slightly or cut a ring into pieces to fill gaps. Nestle a well-drained maraschino cherry in the center of each ring (optional).
Set the pie plate aside while you roll the crust.
Step 6: Cover with crust, vent, and egg wash
On a lightly floured surface, roll the pie dough into a 12-inch circle (about 1/8-inch thick). Carefully drape the dough over the pineapple layer.
Because this is an upside-down pie, you’ll tuck the dough down inside the pie plate rather than crimping over the rim: use your fingers to gently tuck the edges between the fruit and the side of the pie plate. This helps seal in juices and gives the finished pie a neat edge after flipping.
Cut 5–6 small vents in the crust so steam can escape.
Whisk the egg and water together, then lightly brush the crust with egg wash.
Step 7: Bake until deeply golden and bubbling
Set the pie plate on the preheated rimmed sheet pan. Bake at 375°F (190°C) for 45–50 minutes, or until the crust is a deep golden brown and you can see the caramel bubbling at the vents or edges.
If the crust browns too quickly, loosely tent with foil for the final 10–15 minutes.
Step 8: Cool briefly, flip confidently, and let it set
Cool the pie on a rack for 15 minutes. This short rest thickens the caramel slightly so it doesn’t run everywhere, but keeps it warm enough to release cleanly.
Run a thin knife around the inside edge of the pie plate to loosen any sticky spots. Place a large serving plate or platter on top of the pie plate, then, using oven mitts, invert in one smooth, confident motion.
Lift off the pie plate. If any pineapple sticks, just place it back where it belongs while the caramel is still soft.
Let the pie cool for 20 minutes before slicing for the cleanest wedges. Serve warm or at room temperature.
Pro Tips
- Drain and blot the pineapple well. Extra liquid can make the caramel thin and the “base” too soft.
- Use a rimmed sheet pan. Caramel can bubble up and drip; the pan saves your oven and makes cleanup easy.
- Flip at 15 minutes. Too soon and the caramel can run; too late and it can set and stick. Fifteen minutes is the sweet spot.
- Want extra crispness? Use a metal pie plate, and bake until the crust is deeply golden, not just lightly browned.
- Cut with a sharp, thin knife. Wipe the blade between slices to keep the pineapple layer neat.
Variations
- Coconut-Pineapple: Add 1/2 tsp coconut extract (or 2 tbsp sweetened shredded coconut) to the caramel after it comes off the heat.
- Spiced Rum Caramel: Replace 1 tbsp pineapple juice with 1 tbsp dark rum, and add 1/4 tsp ground cinnamon to the brown sugar.
- Cherry-Free, Citrus Finish: Skip the maraschino cherries and serve with a little lemon zest over the warm pie to brighten the caramel.
Storage & Make-Ahead
Storage: Cover leftovers and refrigerate for up to 4 days. The crust will soften slightly over time, but the flavor stays excellent.
Reheating: Warm slices on a baking sheet in a 325°F (163°C) oven for 10–12 minutes, or microwave individual slices for 20–30 seconds (the oven keeps the crust crisper).
Make-ahead: You can make and chill the pie dough up to 2 days ahead. You can also fully bake the pie up to 1 day ahead; cool, cover, and refrigerate. Rewarm before serving, or serve at room temperature.
Nutrition (per serving)
Approximate (1 of 8 slices): 410 calories, 20 g fat, 58 g carbs, 2 g protein, 34 g sugar, 240 mg sodium, 2 g fiber. Values vary by crust choice and exact brands.
