This peach upside-down cake recipe starts with a layer of butter and brown sugar that turns into caramel under sliced peaches while a vanilla cake bakes above it. Once the pan is flipped, that caramel becomes a glossy top instead of a hidden layer at the bottom.
Preheat the oven to 350°F (175°C) and grease a 9-inch round cake pan with butter, or line with parchment.
Melt the butter directly in the pan (or in a saucepan). Sprinkle brown sugar and cinnamon evenly over the butter, tilting to create an even layer.
Pat peach slices dry and arrange them in a single, overlapping layer over the brown sugar, working from the outside edge toward the center.
In a medium bowl, whisk together the flour, baking powder, and salt until combined.
Beat the softened butter and granulated sugar with a hand mixer until pale and fluffy. Add eggs one at a time, then mix in vanilla.
Alternate adding the flour mixture and the milk to the butter mixture, mixing until just combined after each addition. Do not overmix.
Spoon the batter over the peaches in small dollops and spread gently toward the edges so the peaches don't shift. Bake for 45 to 50 minutes.
Let the cake cool in the pan for exactly 10 minutes. Run a knife around the edge, invert onto a serving plate, and lift the pan away.
Notes
Use freestone peaches if buying fresh, since the pit separates easily and won't tear the flesh while slicing.
Slice peaches to an even 1/4-inch (6mm) thickness so they cook through at the same rate as the cake baking around them.
Drain canned peaches thoroughly and pat them dry, since extra liquid thins out the caramel and can make the bottom of the cake soggy once flipped.
Don't skip greasing the pan sides, even though it feels unnecessary with caramel on the bottom, since batter can still stick to the sides of the pan as it rises.
Flip while the cake is still warm, ideally at the 10-minute mark, because the caramel hardens as it cools and becomes harder to release cleanly.
Have the serving plate ready before flipping, since juggling a hot pan and a plate at the same time is where most spills happen.
Check doneness with a toothpick in the center of the cake, not near the edges, where the batter will look and test done well before the middle is fully baked.
Let the caramel cool for a minute before tasting it, since sugar syrup holds heat far longer than it looks like it should.
Bourbon caramel version: Stir 1 tablespoon of bourbon into the melted butter and brown sugar before adding the peaches.
Storage: Store in an airtight container in the fridge for up to 4 days. Reheat individual slices in the microwave for 15-20 seconds to soften the caramel.