Preheat the oven to 350°F (175°C) with a rack in the center. Generously butter and flour a Bundt pan, making sure to get into every nook and cranny, then tap out the excess flour.
Pour the melted butter into the bottom of the pan. In a small bowl, stir together the brown sugar and cinnamon, then sprinkle evenly over the butter.
¼ cup (57 g) unsalted butter, ¾ cup (150 g) packed light brown sugar, ½ tsp. (1 g) ground cinnamon
Blot the pineapple slices and cherries dry with a paper towel. Arrange 8 pineapple rings over the sugar mixture, leaving them whole or slicing them in half. Place a maraschino cherry in the center of each ring. Set the pan aside.
1 (20 oz / 567 g) can pineapple slices, 8 Maraschino cherries
To make the cake batter, beat the eggs and granulated sugar in a large mixing bowl until fluffy and pale, about 3 minutes.
3 large (~ 150 g) eggs, 2 cups (400 g) granulated sugar
Add the melted butter, then the canola oil, and finally the vanilla extract, mixing between each addition. Stir in the buttermilk and Greek yogurt until well blended.
12 tbsps. (170 g) unsalted butter, ⅓ cup (80 ml) canola oil, 2 tsps. (10 ml) vanilla extract, ½ cup (120 ml) buttermilk, ½ cup (120 g) plain, full-fat Greek yogurt
In a separate bowl, sift together the flour, baking powder, baking soda, and salt. Slowly add the dry ingredients to the wet, mixing on low speed until just combined—don’t overmix.
3 cups (375 g) all-purpose flour, 1 tsp. (4 g) baking powder, ½ tsp. (2 g) baking soda, ½ tsp. (3 g) table salt
Spoon the batter over the pineapple layer, then gently tap the pan on the counter to release any air bubbles and level the top.
Bake for 55–60 minutes, or until a toothpick inserted comes out mostly clean with a few moist crumbs.
Let the cake cool in the pan on a rack for at least 1 hour. When ready to flip, do it carefully and let gravity help—don’t rush it. Serve warm or at room temperature.