Topping
6 rings fresh (not canned) pineapple, each 1/2 inch thick, peeled and cored
3 tablespoons unsalted butter+ 1 tablespoon unsalted butter, melted
1/2 cup dark brown sugar, packed
1/2 teaspoon ground cinnamon
Batter
1 cup all-purpose flour
1 teaspoon baking powder
1/2 teaspoon salt
1/4 teaspoon baking soda
1 cup milk
2 large eggs
1 teaspoon vanilla extract
4 tablespoons (1/2 stick) unsalted butter, softened
3/4 cup granulated sugar

1. Prepare the batter by mixing the flour, baking powder, salt and baking soda together in a small bowl. In a large bowl using an electric mixer, cream the butter and sugar on medium-high speed until light and fluffy, 2 to 4 minutes. With the mixer on low, add the eggs, milk and vanilla then gradually add the flour mixture. Blend until smooth, scraping down the sides as necessary. Set aside.
2. Heat the grill. Brush the pineapple rings with the melted butter. Grill them over direct medium heat, with the hood open for about 2 minutes until nicely marked, then turn, grilling the other side for about two minutes. Remove from the grill and let cool while topping is prepared.
3. In a 12-inch cast-iron skillet over direct medium heat, combine the brown sugar, cinnamon and 3 tablespoons butter. Cook until the sugar has melted and the liquid starts to bubble around the outer edge, about 2 minutes. Remove the skillet from the heat and place a whole pineapple ring in the center of the skillet, and then arrange the remaining pineapple rings around it. Using a rubber spatula, spread the batter evenly over the pineapple slices in the skillet.
4. Bake the cake over indirect low to medium heat, keeping the temperature of the grill as close to 350°F as possible, with the hood closed, until the top is golden brown and a skewer inserted into the center comes out clean, 20 to 25 minutes. Turn skillet handle about 180 degrees about 7 to 10 minutes about half way through bake time to prevent an uneven cake. Wearing barbecue mitts to pick up the hot skillet handle, remove the cake from the grill and let cool at room temperature for about 10 minutes.
5. Before removing the cake from the skillet, run a paring knife around the edge to loosen it. Place a serving platter, large enough to hold the cake, over the top of the skillet. Wearing barbecue mitts, carefully invert the skillet and platter at the same time, and then slowly remove the skillet. Replace any pineapple that has stuck to the bottom of the skillet. Let the cake cool briefly before slicing into wedges and serving. The cake is best served warm or at room temperature the day it is made.

Serves: 6 to 8