These unique cookies transform the classic pineapple upside-down cake into handheld treats. The process involves creating a caramelized pineapple topping in mini muffin tins, then adding cookie dough and baking. The cookies are flipped while warm to reveal the glistening fruit topping. Follow these steps carefully for perfect results every time.

1. Step 1: Make sure to grease the muffin cups thoroughly to prevent sticking.

   Preheat oven to 350°F (175°C). Grease 24 cups of a mini muffin tin very well with cooking spray or butter.

2. Step 2: The mixture should be smooth with no sugar granules visible.

   In a small saucepan, melt 1/2 cup butter over medium heat. Add 1/2 cup brown sugar and stir until dissolved, about 2 minutes. Remove from heat.

3. Step 3: Arrange the pineapple pieces in a single layer for even caramelization.

   Spoon about 1 teaspoon of the butter-sugar mixture into each muffin cup. Place a few pineapple tidbits on top of the mixture, then add half a maraschino cherry in the center of each cup.

4. Step 4: Proper creaming incorporates air into the dough, creating a tender cookie texture.

   In a large bowl, cream together the remaining 1/2 cup butter, 1/2 cup brown sugar, and granulated sugar until light and fluffy, about 3 minutes.

5. Step 5: Make sure the egg is fully incorporated before moving to the next step.

   Beat in the egg and vanilla extract until well combined.

6. Step 6: Whisking dry ingredients separately ensures even distribution of leavening agents.

   In a separate bowl, whisk together the flour, baking powder, and salt.

7. Step 7: Avoid overmixing to prevent tough cookies.

   Gradually add the dry ingredients to the wet ingredients, mixing on low speed until just combined. Add the milk and pineapple juice, mixing until the dough comes together.

8. Step 8: Leave a small margin around the edges to allow for spreading during baking.

   Drop about 1 tablespoon of cookie dough on top of each pineapple-cherry arrangement in the muffin cups. Gently press down to spread the dough evenly.

9. Step 9: Rotate the pan halfway through baking for even browning.

   Bake for 12-15 minutes, until the cookies are golden brown around the edges and set in the center.

10. Step 10: This flipping step is crucial - do it while the cookies are still warm to ensure clean release.

    Allow the cookies to cool in the pan for 5 minutes, then place a large baking sheet over the muffin tin and carefully flip it over to release the cookies.

11. Step 11: Use a small offset spatula to gently loosen any stuck pieces.

    If any pineapple pieces or cherries stick to the pan, carefully remove them and place them back on top of the cookies.

12. Step 12: The caramelized topping will soften slightly during storage, enhancing the flavor.

    Allow the cookies to cool completely on a wire rack. Store in an airtight container for up to 3 days.

For a variation, try using different fruits like peaches or apricots in place of pineapple. You can also add a sprinkle of chopped nuts to the caramel layer for added texture. These cookies are best enjoyed within 2-3 days of baking, though they can be gently reheated for 10 seconds in the microwave to restore their just-baked texture.