½ cup unsalted butter, at room temperature
⅔ cup granulated sugar
2 large eggs, room temperature
2 teaspoons pure vanilla extract
1 ⅔ cup all-purpose flour
1 teaspoon baking powder
½ teaspoon baking soda
½ teaspoon kosher salt
½ cup whole milk, room temperature

Spiced Pineapple:
2 cups fresh pineapple chunks {fresh, frozen, and defrosted or canned packed in water} drained well and chopped into small pieces
2 tablespoons brown sugar, packed
1 teaspoon ground cinnamon
⅛ teaspoon kosher salt

1/2 cup all-purpose flour
2 teaspoons brown sugar
½ ground cinnamon
¼ teaspoon kosher salt
2 tablespoons unsalted butter, cold


Preheat oven to 350°F. Line a 9-inch square baking pan with parchment paper, allowing the parchment to run up the sides and slightly over the pan. Grease with cooking spray or butter and set aside.

CAKE: In a large mixing bowl, cream together butter and sugar until smooth. Add eggs and vanilla. Scrape down the bowl as needed. Mix until thoroughly incorporated.

In another bowl, whisk together flour, baking powder, baking soda, and salt. Add half of the flour mixture into the mixing bowl. Stir to combine. Add milk and mix together. Add the remaining flour mixture and continue to mix until there are no longer any dry streaks of flour. The batter will be thick.

PINEAPPLE: Toss pineapple in sugar, cinnamon, and salt. Set aside.

TOPPING: Whisk together flour, sugar, cinnamon, and salt. Using two forks cut cold butter into dry ingredients until the mixture resembles coarse sand. Set aside.

ASSEMBLY: Spread the cake batter into the prepared baking pan. Spread the pineapple mixture (including any juices) on top. Add crumb topping all over.

Bake for 40-45 minutes until a toothpick inserted in the center of the cake comes out clean. Allow cake to cool in pan for 15 minutes before unmolding from pan. Dust with sifted powdered sugar before slicing and serving.