📖 Instructions

1. Before anything else, preheat your oven to 350°F (175°C). Having it ready when you are makes all the difference, trust me. Make sure an oven rack is in the middle position too.
2. Now, let’s prep the skillet. In your 10-inch cast iron skillet (or similar oven-safe pan), melt the 1/2 cup (113g) unsalted butter over medium-low heat. Swirl it around so the bottom and sides of the skillet are thoroughly coated. This is crucial for that beautiful non-stick flip!
3. Sprinkle the 3/4 cup (150g) packed light brown sugar evenly over the melted butter in the skillet. Let it cook gently, stirring occasionally, until the sugar is dissolved and bubbly, forming a rich caramel sauce. This usually takes about 2-3 minutes. Remove from heat immediately.
4. Arrange the drained pineapple slices in a single layer over the caramel mixture in the skillet. You can overlap them slightly if needed to fit. Then, nestle a halved maraschino cherry (or a few!) into the center of each pineapple ring, and scatter any extra cherries in the gaps. Isn't that looking pretty already?
5. Next up, the cake batter. In a large mixing bowl, whisk together the 1 1/2 cups (180g) all-purpose flour, 1 cup (200g) granulated sugar, 1 1/2 teaspoons baking powder, and 1/2 teaspoon salt. Just a quick whisk to combine everything evenly.
6. In a separate medium bowl, or using a stand mixer with the paddle attachment, cream together the 1/2 cup (113g) softened unsalted butter until it's light and fluffy, about 2 minutes. Add the 2 large eggs one at a time, beating well after each addition until fully incorporated. Stir in the 1 teaspoon vanilla extract.
7. Gradually add the dry ingredients to the wet ingredients, alternating with the 1/2 cup (120ml) whole milk, beginning and ending with the dry. Mix on low speed, or by hand with a spatula, just until combined. Be careful not to overmix here; overmixing can lead to a tough cake, and we want tender!
8. Carefully, and I mean *carefully*, pour the cake batter over the pineapple and caramel layer in the skillet. Use your rubber spatula to gently spread the batter evenly to the edges, trying not to disturb the pineapple too much. Give the skillet a gentle tap on the counter a few times to settle the batter and release any air bubbles.
9. Transfer the skillet to your preheated oven. Bake for 35-45 minutes, or until the cake is golden brown, and a wooden skewer or toothpick inserted into the center of the cake comes out clean. Ovens vary, so start checking around 35 minutes.
10. Once baked, take the skillet out of the oven and let it cool on a wire rack for exactly 5-10 minutes. This cooling time is important! Too hot and the cake might fall apart; too cool and it might stick.
11. Now for the grand finale! Place a serving plate (one that's slightly larger than your skillet) upside down over the top of the skillet. Using oven mitts for safety, confidently and quickly flip the skillet and plate over together. Give it a gentle shake, listen for that satisfying *thump*, then carefully lift the skillet. Behold the glorious, perfectly caramelized Pineapple Upside Down Cake! If any pineapple or cherry bits stick to the skillet, just gently place them back onto the cake.
12. Serve your beautiful creation warm, perhaps with a scoop of vanilla ice cream or a dollop of whipped cream. Enjoy every sticky, sweet bite!