Preheat the oven to 350°F. Line two baking sheets with parchment paper.
In a large mixing bowl, beat butter, oil, granulated sugar, and powdered sugar until creamy and light.
1 cup salted butter, 3/4 cup vegetable oil, 1 1/4 cups (250g) granulated sugar, 3/4 cup (90g) powdered sugar
Add eggs, vanilla, and coconut extract. Beat until combined, stopping to scrape bottom and sides of bowl.
2 large eggs, 1 Tablespoon pure vanilla extract, 1 teaspoon coconut extract
Add flour, baking soda, cream of tartar, and salt. Mix on low speed just until combined.
5 1/2 cups (776g) all-purpose flour, 1/2 teaspoon baking soda, 1/2 teaspoon cream of tartar, 1/2 teaspoon salt
Add coconut and 5 tablespoons of crushed pineapple. Mix until combined.
3/4 cup shredded sweetened coconut, 1 (8-ounce) can crushed pineapple
Use a medium cookie scoop to scoop dough into evenly sized balls. Roll dough into balls and space them a few inches apart on a baking sheet lined with parchment paper.
Spray the bottom of a glass or measuring cup with cooking spray then dip in granulated sugar. Gently press each cookie to flatten them out slightly.
Bake for 10-12 minutes until edges of cookies start to turn slightly golden brown. Do not overbake. Cool completely.
To make frosting, beat butter until creamy and smooth using an electric mixer.
1 cup salted butter
Add half of the powdered sugar. Mix on low speed until it starts to come together.
4 cups (480g) powdered sugar
Add remaining powdered sugar, coconut extract, vanilla extract, rum extract, and 3 tablespoons crushed pineapple. Mix on low speed until combined. Increase speed and beat until creamy and light.
3 Tablespoons crushed pineapple, 1 teaspoon coconut extract, 1 teaspoon pure vanilla extract, 1/2 teaspoon rum extract
Frost cooled cookies with a generous swirl of frosting. Sprinkle shredded coconut and top with a maraschino cherry before serving.
Additional shredded sweetened coconut, 24 maraschino cherries