Creating Pineapple Upside Down Sugar Cookies is easy if you follow these simple steps:

1. Preheat the Oven: Preheat your oven to 350°F (175°C) and line a baking sheet with parchment paper.
2. Cream Butter and Sugar: In a large mixing bowl, cream together the softened butter and granulated sugar until light and fluffy.
3. Add Eggs and Vanilla: Beat in the eggs one at a time, followed by the vanilla extract, mixing well after each addition.
4. Combine Dry Ingredients: In a separate bowl, whisk together the flour, baking soda, and salt.
5. Mix Dry and Wet Ingredients: Gradually add the dry mixture to the wet ingredients, stirring until just combined.
6. Prepare Pineapple Topping: In a small bowl, mix the drained crushed pineapple with brown sugar.
7. Form Cookies: Use a tablespoon to scoop cookie dough onto the prepared baking sheet, spacing them about 2 inches apart.
8. Top with Pineapple: Press a spoonful of the pineapple mixture onto the center of each cookie, followed by a maraschino cherry.
9. Bake: Place the baking sheet in the preheated oven and bake for 10-12 minutes or until the edges are lightly golden.
10. Cool: Allow the cookies to cool on the baking sheet for 5 minutes before transferring them to a wire rack to cool completely.

By following these steps, you’ll create a batch of Pineapple Upside Down Sugar Cookies that are not just tasty but also a feast for the eyes!