These pineapple upside-down sugar cookies reimagine a classic dessert in a smaller, more playful form. Inspired by pineapple upside-down cake, they combine familiar flavors with the simplicity of a cookie, resulting in a treat that feels both nostalgic and lighthearted. They’re well suited for casual gatherings or relaxed home baking.
The cookies themselves are soft, buttery, and mildly sweet, providing a neutral base that highlights the fruit topping. A pineapple ring placed on each cookie caramelizes gently in the oven, adding moisture, brightness, and a subtle tang. This contrast keeps the cookies from feeling overly rich while enhancing their overall appeal.
Preparation begins by creaming softened unsalted butter with granulated sugar until the mixture becomes light and fluffy. This step is essential for creating a tender texture. An egg and vanilla extract are then added, contributing richness and depth while helping bind the dough together smoothly.
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