Step 1: Preheat your oven to 325°F (160°C). Grease and flour a 10-12 cup Bundt pan thoroughly, ensuring every crevice is coated. This is crucial for easy release.
Step 2: In a large mixing bowl, using an electric mixer, cream together the softened butter and granulated sugar until light and fluffy, about 5-7 minutes. This step incorporates air, which helps create a tender cake.
Step 3: Add the softened 8-ounce package of cream cheese to the butter mixture and beat until fully combined and smooth, scraping down the sides of the bowl as needed.
Step 4: Beat in the eggs, one at a time, mixing well after each addition until just incorporated. Stir in the vanilla extract.
Step 5: In a separate medium bowl, whisk together the all-purpose flour, baking powder, and salt.
Step 6: Gradually add the dry ingredients to the wet ingredients, alternating with the 1/2 cup milk. Begin and end with the dry ingredients. Mix on low speed until just combined, being careful not to overmix the batter.
Step 7: Gently fold in the very well-drained crushed pineapple. Ensure the pineapple is evenly distributed throughout the batter.
Step 8: Pour the batter evenly into your prepared Bundt pan. Tap the pan gently on the counter a few times to release any air bubbles and help the batter settle.
Step 9: Bake for 60-75 minutes, or until a wooden skewer or toothpick inserted into the center of the cake comes out clean. If the top begins to brown too quickly, you can loosely tent it with aluminum foil.
Step 10: Once baked, remove the cake from the oven and let it cool in the pan on a wire rack for 15-20 minutes. This allows the cake to set before inverting.
Step 11: After cooling slightly, carefully invert the cake onto the wire rack to cool completely. The cake must be entirely cool before glazing.
Step 12: While the cake cools, prepare the glaze: In a medium bowl, whisk together the softened 4 ounces of cream cheese, powdered sugar, 2 tablespoons of milk (or pineapple juice), and 1/2 teaspoon vanilla extract until smooth and creamy. If the glaze is too thick, add more milk 1 teaspoon at a time until desired consistency. If too thin, add more powdered sugar.
Step 13: Once the Heavenly Pineapple Cream Cheese Pound Cake is completely cool, generously drizzle the cream cheese glaze over the top, letting it drip down the sides. Serve and enjoy!