Classic Pineapple Upside-Down Cake

Directions

Prepare Oven and Pan

  1. Adjust oven rack to middle position and preheat oven to 350°F (177°C).
  2. Lightly grease the bottom and sides of an 8 ½ x 2 ½-inch or 9 x 2-inch round cake pan with vegetable oil.

Topping

3. In a bowl, use a handheld or stand mixer fitted with a paddle to combine butter, honey, brown sugar, and vanilla over medium speed for 30 seconds.
4. Evenly spread brown sugar mixture over the bottom of the prepared pan.
5. Place one pineapple ring in the center and six around the edges of the pan.
6. Place two maraschino cherries in the center of each pineapple ring.
7. Sprinkle walnuts around the edges where brown sugar is exposed and fill small gaps between the rings with broken walnut pieces.

Cake Batter

8. Sift flour and baking powder into a medium bowl; whisk to combine.
9. In a separate medium bowl, add softened butter and granulated sugar. Using a paddle attachment, mix on low speed for 20 seconds, then increase to medium and beat for 3 minutes until light and creamy. Scrape down the sides as needed.
10. Mix in vanilla extract for 10 seconds on medium speed.
11. Add eggs one at a time, mixing on medium speed for 30 seconds each, scraping the bowl after each addition.
12. Add milk and mix on medium speed for 15 seconds.
13. On low speed, add flour mixture in 3 batches, mixing until just combined (about 10 seconds each). Scrape the sides as needed.
14. Pour batter evenly over the pineapples. Use a spatula to spread it; batter will be thick.

Bake and Cool

15. Bake 30–40 minutes, or until cake is golden brown, springs back when touched, and a toothpick inserted in the center comes out clean with a few crumbs. Cake’s internal temperature should be 185–190°F (85–88°C).
16. Cool cake in pan on a rack for 45–60 minutes. Cake should still be slightly warm to prevent topping from sticking.
17. Run a knife around the edges, invert onto a serving platter, and wait 5 minutes before lifting off the pan. Serve warm.

Recipe Details

Prep time: 20 minutes
Cook time: 30–40 minutes
Total time: 1 hour
Servings: 8
Difficulty: Medium

Variations & Substitutions

  • Fruit swaps: try mandarin oranges or peaches instead of pineapple.
  • Nut options: use pecans or almonds instead of walnuts.
  • Honey substitute: maple syrup can replace honey for a slightly different flavor.
  • Mini cakes: bake in individual ramekins for personal servings.

Serving Suggestions

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