Preheat the oven to 350°F. Lightly grease a standard 24-cup mini muffin pan, or spray well with nonstick baking spray.

Prepare the topping by stirring together the melted butter, 3/4 cup brown sugar, and 1/4 teaspoon salt in a small bowl until combined and glossy.

Spoon about 1 teaspoon of the brown sugar–butter mixture into the bottom of each mini muffin cup, spreading it lightly to cover the base.

Place 3–4 pineapple tidbits on top of the caramel mixture in each cup, arranging them in a single layer. Add half a maraschino cherry, cut side down, in the center of each cup. Set the pan aside.

In a medium bowl, whisk together the flour, baking powder, and 1/2 teaspoon salt until well combined; set aside.

In a large mixing bowl, beat 3/4 cup softened butter, granulated sugar, and 1/4 cup brown sugar with a hand mixer or stand mixer on medium speed until light and fluffy, 2–3 minutes.

Add the egg, egg yolk, vanilla extract, and almond extract (if using) to the butter mixture and beat until smooth, scraping down the bowl as needed.

Add the dry ingredients to the wet ingredients in two additions, mixing on low speed just until a soft, thick dough forms. If the dough seems very stiff or crumbly, mix in 1–2 tablespoons of pineapple juice or milk, a little at a time, until it holds together smoothly.

Chill the dough in the refrigerator for about 20 minutes to firm slightly and help prevent spreading under the juicy topping.

Scoop about 1 tablespoon of dough for each cookie and roll into balls. Place one dough ball on top of the pineapple and cherry in each muffin cup, then gently flatten with your fingers so the dough fills the cup and covers most of the fruit.

Bake the cookies for 12–15 minutes, or until the edges look set and lightly golden and the centers are no longer shiny.

Remove the pan from the oven and let the cookies cool in the pan for 5–7 minutes to allow the caramel to thicken slightly.

Run a small offset spatula or butter knife around the edges of each cookie to loosen, then carefully lift and flip each one out onto a cooling rack or parchment-lined sheet, pineapple side up. If any fruit sticks, gently spoon it back onto the top.

Cool the cookies until just warm or room temperature before serving. Serve slightly warm on their own or with a small scoop of vanilla ice cream if desired.