Pineapple Upside-Down Cookies - A Recipe from Scratch

      Recipe by Erin Jeanne McDowell

      “What do you get when you blend a soft, cakey cookie with a traditional pineapple upside-down cake? It’s juicy, caramelized, buttery—and most importantly, it’s easy to take on the go!”—Erin Jeanne McDowell, 2026 contributing editor

      **Cookie Dough:**

      - 2 ⅓ cups (208 grams) all-purpose flour

      - ½ teaspoon baking soda

      - ¼ teaspoon fine sea salt

      - ¼ cup (60 grams) sour cream, at room temperature

      - 1 large egg (50 grams), at room temperature

      - 1 teaspoon vanilla extract

      - 4 tablespoons (56 grams) unsalted butter, at room temperature

      - ⅔ cup (80 grams) powdered sugar

      - 3 tablespoons (42 grams) light brown sugar

      **Assembly:**

      - ¾ cup (165 grams) light brown sugar

      - 6 tablespoons (84 grams) unsalted butter, melted

      - 12 canned pineapple rings, patted dry

      - 12 stemless maraschino cherries, patted dry

      Preheat your oven to 350°F (180°C) and position the oven racks in the upper and lower thirds. Lightly grease two 4-inch bun pans (6-well) with cooking spray.

      **Prepare the cookie dough:** In a medium bowl, whisk together the flour, baking soda, and salt. In a liquid measuring cup, whisk the sour cream, egg, and vanilla extract until well combined. Use a hand mixer to cream the butter, powdered sugar, and brown sugar in a separate bowl at medium speed until the mixture is light and fluffy, about 3 to 4 minutes. Make sure to scrape the bowl’s base and sides thoroughly. (A silicone spatula can also be used for this step, as the amount is too small for a standard electric stand mixer.) Incorporate the sour cream mixture, mixing on medium speed until fully combined and again scraping the bowl thoroughly. Gradually add the dry ingredients in 2 to 3 portions, mixing on low speed only until combined.

      **Assemble the cookies:** In a small bowl, combine the brown sugar and melted butter. Scoop a heaping tablespoon (approximately 19 grams) of this mixture into each prepared well. Use a small offset spatula (or your hands) to spread it into an even layer. Place a pineapple ring in the bottom of each well, and position a cherry in the center of the pineapple ring, pressing down slightly.

      Scoop the cookie dough using 2-tablespoon (about 38 grams) portions and place it on top of the pineapple. With a damp hand, gently press the cookie dough to flatten it, covering the pineapple completely.

      Transfer the pans to the oven, swapping them halfway through baking, until the cookies are golden brown around the edges, about 14 to 17 minutes. Once done, take the cookies out of the oven and let them cool in the pan for 5 minutes. Meanwhile, line two baking sheets with parchment paper. After the cooling period, invert the pans quickly and firmly onto one of the prepared sheets. Use a spatula to move the unmolded cookies to the other baking sheet, discarding any excess syrup and juices.

      Let the cookies cool for at least 8 minutes (or until fully cooled) before serving. Store in an airtight container for up to 3 days.

      We’d love to hear your thoughts!