For the Pineapple Sugar Cookies:

• ▢ 1 ½ sticks unsalted butter, at room temperature (3/4 cup)
• ▢ ¾ cup granulated sugar
• ▢ 1 large egg
• ▢ ½ tsp pineapple extract or flavor, adjust to your desired intensity
• ▢ 2 ¼ cups all-purpose flour
• ▢ ½ tsp baking powder

For the Buttercream Frosting:

• ▢ 1 stick unsalted butter, at room temperature (1/2 cup)
• ▢ ½ cup vegetable shortening
• ▢ 2.5-3 cups powdered sugar, sifted for best results
• ▢ Yellow and green gel food coloring

For the Pineapple Sugar Cookies:

• In a large mixing bowl, use an electric mixer to beat the room temperature unsalted butter until it is light and fluffy, about 2-3 minutes. This aerates the butter, contributing to a tender cookie. Add the granulated sugar and continue beating until the mixture is well combined and has a pale, fluffy consistency.
• Crack in the large egg and add the pineapple extract or flavor. Beat for another 1-2 minutes, ensuring all wet ingredients are fully incorporated. Scrape down the sides of the bowl as needed to ensure even mixing.
• In a separate bowl, whisk together the all-purpose flour and baking powder. Gradually add about one-third of the dry ingredients to the wet mixture, mixing on low speed until just combined. Continue adding the remaining flour in two more additions, mixing until no dry streaks remain. Be careful not to overmix, as this can lead to tough cookies. If the dough seems excessively sticky, add 1 tablespoon of flour at a time until it’s workable but still soft.
• Divide the prepared dough into two equal portions. Gently flatten each portion into a disk, wrap tightly in plastic wrap, and refrigerate overnight (or for at least 4 hours). Chilling the dough is crucial for preventing spread and ensuring your pineapple shapes hold their form beautifully during baking.
• Once the dough is thoroughly chilled, remove one disk from the refrigerator. On a lightly floured silicone baking mat or a sheet of parchment paper, roll the dough out evenly to a thickness of approximately 1/8 to 1/4 inch, depending on your preferred cookie texture. Thinner cookies will be crispier, while thicker ones will be softer.
• Carefully transfer the rolled dough on its mat/parchment paper to the freezer for 15 minutes. This quick chill helps the cookies maintain their shape when cut.
• While the dough is chilling, preheat your oven to 350°F (175°C). Prepare baking sheets by lining them with parchment paper or silicone baking mats.
• After 15 minutes, retrieve the dough from the freezer. Using your pineapple cookie cutter, cut out as many shapes as possible, placing them about 1-inch apart on your prepared baking sheets. Place the cut-out cookies (on the baking sheets) back into the freezer for another 10-15 minutes. This double-chill method is key to sharp, distinct cookie shapes and preventing them from spreading in the oven.
• Bake the cookies for 9-10 minutes. For even baking, rotate the baking pan halfway through the cooking time. The cookies should be very light in color, with possibly just a hint of golden on the edges, when you remove them from the oven. Do not overbake, as this will dry them out.
• Allow the freshly baked cookies to cool on the baking pan for at least 10 minutes before carefully transferring them to a wire cooling rack to cool completely. This prevents them from breaking and allows them to firm up.
• Gather any dough scraps, gently re-roll them, chill briefly, and repeat the cutting and baking process until all the dough is used up. Repeat this entire process with the second disk of dough.

For the Buttercream Frosting and Decorating:

• In a clean mixing bowl, combine the room temperature unsalted butter and vegetable shortening. Using an electric mixer, beat on medium-high speed for 1-2 minutes until the mixture is wonderfully light and fluffy. This creates the essential airy base for your buttercream.
• Gradually add the sifted powdered sugar, about 1 cup at a time, beating slowly until each addition is fully incorporated before adding more. Continue until you achieve a creamy, pipeable consistency. If the frosting seems too stiff, add a tiny splash of milk or cream (1 teaspoon at a time). If it’s too thin, add a bit more powdered sugar. For best results and to avoid a powdery mess, I often recommend starting to mix the buttercream by hand with a spatula to incorporate the first cup of powdered sugar, then use the electric mixer to achieve ultimate smoothness and fluffiness.
• Divide the prepared buttercream frosting into two separate bowls. Allocate a larger portion to one bowl for the yellow pineapple body (about 2/3 of the frosting) and a smaller portion to the other for the green leaves (about 1/3 of the frosting). Add yellow gel food coloring to the larger bowl and green gel food coloring to the smaller bowl. Mix each thoroughly until you achieve your desired vibrant shades. Gel food colorings are recommended as they provide intense color without significantly altering frosting consistency.
• Prepare a piping bag fitted with a Wilton #18 star tip for the yellow frosting. Begin to frost the pineapple portion of your cooled cookies. To create the characteristic spiky texture of pineapple skin, apply steady pressure to the piping bag, then slightly lift the tip away from the cookie as you release pressure, creating a small “star” or “spike.” Work your way from the bottom of the pineapple shape to the top, repeating this technique until the entire yellow section is covered.
• Next, prepare another piping bag, this time fitted with a Wilton #5 round tip, for the green frosting. Pipe the leafy crown of the pineapples. Start piping near the top edge of the yellow pineapple body and extend outwards, lifting the piping bag slightly at the end of each “leaf” to create a natural, spiky leaf effect. Continue until all the cookies have their delightful green leafy tops.

For frosting, I specifically used a Wilton #18 star tip for creating the textured yellow pineapple body and a Wilton #5 round tip for piping the green leaves. These tips help achieve the realistic look of the fruit.

Ensure butter and eggs are at room temperature for optimal dough consistency. This allows ingredients to cream together smoothly, resulting in a lighter, more tender cookie texture.

Proper chilling of the cookie dough is paramount for maintaining the intricate pineapple shape. Do not skip or shorten the refrigeration and freezing steps; they are crucial for preventing cookie spread.

Nutrition Information (per cookie)

Nutrition Disclosure

All nutritional values are approximate and provided to the reader as a courtesy. These estimations are based on standard ingredient calculations and may vary depending on brands, precise measurements, and preparation methods. Changing ingredients and/or quantities will significantly alter the estimated nutritional calculations. We highly recommend consulting a professional nutritionist or using a verified nutrition calculator for precise dietary information tailored to your specific needs.