Preheat the oven to 350 degrees Fahrenheit. Generously spray a 12-cup bundt pan with non-stick cooking spray. Dust the inside with flour and set aside.
In a large bowl combine 1 (15.25-ounce) boxed pineapple cake mix,½ cup water, ½ cup pineapple juice, 3 large eggs, ⅓ cup vegetable or canola oil. Mix until combined using an electric hand mixer. Pour the batter into the prepared pan and spread it out evenly.
In a large bowl combine 1 (8-ounce) package cream cheese, 2 tablespoon unsalted butter, and 1 tablespoon cornstarch. Mix until smooth and creamy. Add 1 large egg, 1 teaspoon vanilla extract, and 1 (14-ounce) can sweetened condensed milk and mix until well combined.
Spoon the cheesecake layer over the cake batter in an even ring, being careful not to touch the outer or inner part of the bundt pan. Bake in the preheated oven for 50-55 minutes or until a toothpick inserted in the center comes out clean.
Remove the cake from the oven and cool it in the pan for 10 minutes before inverting it to a wire rack to cool completely.
Add ¼ cup white chocolate chips to a medium bowl and microwave until melted, stirring every 30 seconds. Stir in the ¾ cup powdered sugar. Add 1 teaspoon vanilla extract and 1 - 2 tablespoons pineapple juice then stir until smooth and well combined. If the mixture is too thick, add a little more pineapple juice.
Drizzle the glaze over the cooled cake. Allow glaze to set then top it with chopped pineapple, for serving. Store in the refrigerator until serving.