1. Preheat your oven to 350°F and line a baking sheet with parchment paper. This step is key for easy cleanup, especially when you’re racing against the clock after a busy day.
2. In a medium bowl, whisk together the flour, baking powder, baking soda, salt, and cinnamon if using. Setting these dry ingredients aside helps everything blend smoothly later on.
3. In a large bowl, beat the softened butter with the brown sugar and granulated sugar until light and fluffy, about 3-4 minutes. I always take a moment here to really enjoy the creamy texture—it’s a small pause to appreciate the magic happening.
4. Add the egg and vanilla extract to the butter mixture and beat until fully combined. The batter will start to get rich and glossy, which is a good sign you’re on the right track.
5. Gradually add the dry ingredients to the wet ingredients, mixing just until combined. Over-mixing can toughen the cookies, so I always remind myself: gentle is better.
6. Fold in the crushed pineapple and pineapple juice gently, making sure the fruit is evenly distributed but the dough stays light.
7. Using a tablespoon or small cookie scoop, drop dollops of dough onto the prepared baking sheet, spacing them about 2 inches apart. They won’t spread too much, but giving them room helps maintain their pretty shape.
8. For that signature upside-down look, press a small pineapple chunk or a few crushed pieces on top of each cookie before baking. This is where the caramel magic begins!
9. Bake for 12-15 minutes, or until the edges are golden and the tops look set. Be careful not to overbake, or you’ll lose that tender chewiness I love so much.
10. Remove from the oven and let the cookies cool on the baking sheet for about 5 minutes before transferring them to a wire rack to cool completely. This wait is hard, but trust me—it’s worth it.

These steps remind me of the afternoons I spent cooking with my grandmother, where every part of the process was a lesson in patience and love. Even when life feels like a whirlwind, taking that time to bake creates moments that linger far beyond the kitchen.