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Preheat oven to 350°F.
Place the pineapple in a colander. Press with a spatula to drain out the pineapple juice (reserve 1 tablespoon of the juice for the frosting). It doesn’t have to be completely dry but try to get most of the juice out.
In the bowl of a stand mixer, place the butter, white sugar, and brown sugar. Mix on medium speed for 2 minutes, until light and fluffy. Add the eggs, one at a time, beating in between additions.
Beat in the vanilla and pineapple.
In a medium bowl, whisk together the flour, salt, baking powder, and baking soda. Add the flour mixture to the stand mixer, and stir until combined.
Drop 2-tablespoon sized scoops onto a baking sheet. Bake for 10–12 minutes, or until light brown on the bottom and the cookies no longer look wet on top. Let cool completely.
For the frosting, combine all ingredients in a large bowl. Beat with a hand mixer until light and fluffy.
Spread the frosting on top of the cooled cookies.