In a large bowl, beat a 1/2 cup butter with the cream cheese so it’s light and fluffy on medium speed. Add the cream and sugar and mix until combined.
Beat in the vanilla and egg to the creamed mixture. Scrap down the sides of the bowl as needed. In a small bowl, whisk together the dry ingredients.
With the mixer on low, add the dry ingredients to the wet ingredients a little at a time until mixed.
Pour in the drained pineapple and stir again.
Scoop out 2 tablespoons of cookie at a time and place them on the prepared cookie sheet 2 inches apart. Bake for 10-12 minutes in the preheated oven until the tops appear matte.
Place cookies on a wire rack to cool. In a separate bowl, combine confectioners’ sugar and enough pineapple juice to have a pourable glaze.
Drizzle over the tops of the cookies or dip one side in and serve once it has set.