Meta Info
Servings: 20–22 cookies
Total Time: 30 minutes
Difficulty: Easy
Calories per Serving: ~150
Macros (per cookie, estimated):
Protein: 2g | Carbs: 20g | Fat: 7g | Fiber: 0.5g
Intro Paragraph (SEO + Emotional Hook)
These Pineapple Upside Down Sugar Cookies are everything you love about the classic retro dessert—sweet pineapple, buttery sugar cookie, and caramelized edges—wrapped into a soft, bakery-style cookie you can make in under 30 minutes. They’re nostalgic, comforting, and surprisingly simple, making them perfect for holidays, potlucks, or anytime you want a cheerful homemade treat.
What makes these pineapple upside down sugar cookies special is the contrast in textures: a tender, vanilla-scented cookie base topped with juicy pineapple rings that bake into a lightly caramelized, golden finish. They look impressive, taste indulgent, and don’t require any fancy techniques.
Whether you’re baking for family, guests, or just yourself, this recipe delivers big flavor with minimal effort—classic comfort baking at its best.
Look at the Recipe
- Soft, buttery sugar cookies with caramelized pineapple on top
- Sweet, nostalgic flavors inspired by classic pineapple upside down cake
- Easy dessert recipe perfect for parties, holidays, or casual baking
Ingredients Needed
- 1 cup unsalted butter, softened
- 1 cup granulated sugar
- 1 large egg
- 1 teaspoon vanilla extract
- 2 cups all-purpose flour
- 1 teaspoon baking soda
- ½ teaspoon salt
- 10–12 canned pineapple rings, well-drained and patted dry
- Additional granulated sugar, for sprinkling
How to Make Our Pineapple Upside Down Sugar Cookies
- Preheat your oven to 350°F (180°C). Line baking trays with parchment paper for easy cleanup.
- In a large bowl, cream the softened butter and sugar until light and fluffy, about 2–3 minutes using an electric mixer.
- Beat in the egg and vanilla extract until smooth and fully incorporated.
- In a separate bowl, whisk together the flour, baking soda, and salt. Gradually mix the dry ingredients into the wet ingredients just until a soft dough forms. Avoid overmixing.
- Scoop about 2 tablespoons of dough per cookie onto the prepared baking sheets, spacing them about 2 inches apart.
- Press a dried pineapple ring gently onto each dough mound, flattening slightly. Trim or halve rings if needed to fit.
- Sprinkle a light dusting of sugar over the pineapple for extra caramelization.
- Bake for 11–13 minutes, until the edges are lightly golden and the centers are set.
- Cool on the baking tray for 3–5 minutes, then transfer to a wire rack to cool completely.
These cookies firm up slightly as they cool while staying soft inside.
Storage & Serving Suggestions
- Store cookies in an airtight container at room temperature for up to 3 days.
- Refrigerate for up to 5 days if your kitchen is warm.
- Serve with coffee, tea, or as a light dessert after dinner.
- For entertaining, garnish with a small maraschino cherry piece in the center of each pineapple ring.
Tips & FAQs
Can I make these ahead of time?
Yes. Bake them a day in advance and store in an airtight container until serving.
Can I use fresh pineapple instead of canned?
You can, but make sure it’s very thinly sliced and thoroughly patted dry to avoid excess moisture.
How can I make these slightly higher in protein?
Swap ¼ cup of the flour for vanilla protein powder or serve alongside a high-protein yogurt for balance.
Can I freeze these cookies?
Yes. Freeze fully cooled cookies in a single layer, then transfer to a freezer-safe container for up to 2 months.
Do I need to flip them like a cake?
No flipping required—these cookies bake pineapple-side up for easy serving.
SEO Enhancements
Main Keyword: Pineapple Upside Down Sugar Cookies
Semantic Variations:
easy pineapple cookies, upside down cookie recipe, homemade sugar cookies, retro dessert recipe
Internal Link Suggestions:
High-Protein Pancakes | Protein Oatmeal Cups | 7-Day Meal Plan
If you’d like, I can also:
- Create a high-protein dessert variation
- Add a Pinterest-optimized intro
- Estimate Weight Watchers points
- Convert this into a low-sugar or gluten-free version
Just tell me 👍
