Description

Pineapple Upside Down Sugar Cookies combine the tropical sweetness of caramelized pineapple with soft, tender sugar cookie dough. These visually stunning and delicious cookies offer a bright, tangy flavor with a perfect soft-chewy texture, made with simple pantry staples and plant-based ingredients. Ideal for sharing at any occasion and customizable to suit dietary preferences.

Ingredients

Scale

Cookie Dough

2 cups all-purpose flour
3/4 cup granulated sugar
1/2 cup vegan butter (plant-based), softened
1 tsp baking powder (natural)
1 tsp vanilla extract (natural)
1 tbsp apple cider vinegar (natural)

Pineapple Topping

Fresh pineapple slices, enough for one slice per cookie (about 1 cup)
1/2 cup brown sugar (natural)
1 tbsp vegetarian Worcestershire sauce (natural)
1 tsp apple cider vinegar (natural)
Natural gelling agent, a light sprinkle to help topping hold

Instructions

Prepare the Pineapple Topping: Heat brown sugar (natural), vegetarian Worcestershire sauce (natural), and apple cider vinegar (natural) in a saucepan over medium heat until smooth and caramel-like. Gently fold in fresh pineapple slices so they are lightly coated and warm, perfect for caramelization and a glossy finish.
Make the Cookie Dough: In a mixing bowl, cream together vegan butter (plant-based) and granulated sugar until light and fluffy. Stir in vanilla extract (natural) and apple cider vinegar (natural). Gradually add all-purpose flour and baking powder (natural), mixing until just combined to keep the texture soft and tender.
Assemble the Cookies: Spoon a portion of cookie dough into each mold or onto a lined baking sheet, then gently press a caramelized pineapple slice on top of each cookie. Sprinkle a small amount of natural gelling agent over the pineapple topping to help it hold its shape during baking.
Bake to Perfection: Bake the cookies in a preheated oven at 350°F (175°C) for 12-15 minutes or until edges are golden and the pineapple topping is beautifully caramelized. Allow cookies to cool before carefully removing from molds or baking sheet to reveal the charming upside down presentation.

Notes

Use fresh pineapple slices for best caramelization and vibrant flavor.
Mix the dough just until ingredients come together to avoid tough cookies.
If dough feels too soft, chill briefly to help with shaping and prevent spreading.
Line baking sheets with parchment paper or silicone mats to prevent sticking and ensure clean edges.
Stir caramel mixture continuously over medium heat to prevent burning.

Prep Time: 20 minutes
Cook Time: 15 minutes
Category: Appetizers
Method: Baking
Cuisine: American

Nutrition

Serving Size: 1 cookie
Calories: 150
Sugar: 12g
Sodium: 50mg
Fat: 6g
Saturated Fat: 1g
Unsaturated Fat: 4g
Trans Fat: 0g
Carbohydrates: 22g
Fiber: 1g
Protein: 1g
Cholesterol: 0mg

Keywords: pineapple upside down cookies, sugar cookies, caramelized pineapple, vegan cookies, tropical dessert, plant-based baking