Preheat your oven to 350°F (175°C). Grease a 9x13-inch baking dish with butter or cooking spray.

In a medium bowl, beat the softened cream cheese with 1/4 cup sugar until smooth. Fold in pineapple chunks with juice and vanilla extract. Spread evenly in the baking dish.

In a separate bowl, whisk together flour, baking powder, and salt. Cut in cubed butter until mixture resembles coarse breadcrumbs.

Pour milk into the flour mixture and stir gently with a fork until just combined. Do not overmix.

Drop spoonfuls of batter over the pineapple-cream cheese filling, leaving small gaps. Sprinkle remaining 1/2 cup sugar over the top.

Bake for 35-40 minutes until the topping is golden brown and a toothpick inserted into the topping comes out clean.

Remove from oven and let rest for 5-10 minutes. Dust with powdered sugar and serve warm with vanilla ice cream or whipped cream.