Preheat & Prepare Pan: Preheat oven to 325°F (165°C). Grease and flour a 16–18 cup bundt or tube pan.
Mix Wet Ingredients: In a large bowl, cream together butter, shortening, sugar, and cream cheese until light and fluffy. Beat in eggs one at a time, then add vanilla, cake batter extract, and pineapple extract (if using).
Combine Dry Ingredients: In a separate bowl, whisk together flour, baking powder, and salt.
Alternate Mixing: Gradually add the dry ingredients to the wet ingredients, alternating with buttermilk, beginning and ending with the flour mixture. Fold in the crushed pineapple.
Bake: Pour batter into prepared pan. Smooth the top. Bake for 1 hour 45 minutes to 2 hours, or until a toothpick inserted in the center comes out clean. Let cake cool in the pan for 15 minutes, then invert onto a wire rack to cool completely.
Prepare Glaze: In a small bowl, whisk together powdered sugar, milk (or pineapple juice), and vanilla until smooth. Adjust consistency if necessary.
Glaze & Serve: Drizzle glaze over the cooled cake. Slice and enjoy!
