Preheat the oven to 350°F and line baking sheets with parchment paper.
In a large mixing bowl, beat the butter and cream cheese together until light and fluffy (about 2 minutes on medium speed). Add sugar and cream together for a minute more.
Add the vanilla extract and egg; beat until combined. Use a rubber spatula to scrape the sides of the mixing bowl.
Whisk together the flour, baking powder, and salt in a medium bowl.
With the mixer running on low speed, add the flour mixture to the creamed ingredients a bit at a time until fully incorporated.
Add in the drained pineapple and mix until evenly combined.
Use a 2-tablespoon cookie dough scoop to scoop balls of dough. Place them 2 inches apart on a parchment-lined sheet pan.
To make smoother cookies, chill the scooped dough balls in the freezer for 5-10 minutes and then roll them quickly in the palms of your hands to form a smooth ball. You can alternately bake the dropped scoops of cookies. They will bake the same; they will just be slightly lumpier.
Bake cookies for 10 to 12 minutes until the dough has puffed and appears matte (not wet) across the surface and the bottom edges are just beginning to brown.
Transfer cookies to a cooling rack and let them cool.
Whisk together the powdered sugar and enough pineapple juice to form a glaze of desired drizzling consistency. Drizzle the glaze over the cookies or dip the top of each cookie into the glaze.
Allow the glaze 15 minutes to set on top of the cookies. Serve.
Notes
You can add up to 1 cup of drained crushed pineapple to the cookie dough. Adding more than that may change the consistency of the dough by adding too much moisture.
The dough is very soft and sticky but does not necessarily need to be chilled to bake properly. Chilling the dough makes it easier to roll the dough into smooth balls. You can also dip your hands in water to prevent the dough from sticking. Or simply drop the dough by the spoonful onto the cookie sheet and bake it as is.
Oven temperatures vary and may need to be recalibrated periodically to ensure they are accurate. Make sure to check your cookies at the lower end of the recommended baking time.