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Preheat your Kamado Joe for indirect cooking at 360°F (182°C), using apple or cherry wood pellets for a sweet smoke flavour.
In a saucepan, melt ½ cup butter over medium heat. Stir in brown sugar until fully combined and slightly bubbly.
Pour the caramel mixture into a greased 9-inch round cake pan, then arrange pineapple slices on top. Set aside.
In a medium bowl, whisk together flour, baking powder, and salt.
In a large mixing bowl, cream softened butter and granulated sugar until light and fluffy. Beat in the eggs one at a time, followed by vanilla extract.
Gradually add the dry mixture to the wet ingredients, alternating with milk and pineapple juice, starting and ending with the dry ingredients. Mix just until combined.
Pour the batter evenly over the pineapple slices in the cake pan.
Place the pan on the grill for indirect heat cooking, using a heat deflector if necessary. Close the lid and smoke for 35–45 minutes, or until a toothpick inserted into the center comes out clean. If the top browns too quickly, loosely cover with foil.
Remove the cake from the grill and let it cool for 10 minutes. Place a serving plate over the pan, invert, and let sit for a minute to release the topping. Gently lift off the pan, then slice and serve warm — optionally with vanilla ice cream.