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Sweet Holiday Cookies

Featured in Irresistible Desserts.

Turn beloved pineapple upside-down cake into bite-sized cookies. Soft sugar cookies topped with pineapple-brown sugar mixture and bright red cherries for a festive treat.

Casey
Updated on Mon, 20 Jan 2025 20:07:27 GMT
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A plate of pineapple upside-down cake slices topped with cherry preserves. Pin it
A plate of pineapple upside-down cake slices topped with cherry preserves. | cookingwithcasey.com

Let me share these festive Christmas Pineapple Upside-Down Sugar Cookies that combine two classic favorites! I love how they bring together buttery sugar cookies with that amazing caramelized pineapple and cherry topping. They're such a fun twist for holiday cookie platters.

A Nostalgic Holiday Treat

What makes these cookies so special is how they capture all the wonderful flavors of pineapple upside-down cake in a cute cookie form. They're simple to make but look absolutely beautiful with those bright cherries and golden pineapple. Everyone from kids to adults can't resist them.

What You'll Need

  • For the Cookies: - Soft butter - Regular sugar - Fresh egg - Pure vanilla - All-purpose flour - Baking powder and salt
  • For the Magic Top: - Bright maraschino cherries - Well-drained crushed pineapple - Brown sugar for caramel
A close-up image of a decorative plate featuring stacked pineapple slice desserts topped with cherry preserves. Pin it
A close-up image of a decorative plate featuring stacked pineapple slice desserts topped with cherry preserves. | cookingwithcasey.com

Let's Start Baking

Make the Topping:
Mix your drained pineapple with brown sugar set aside.
Create the Dough:
Cream butter and sugar add egg and vanilla then mix in dry ingredients.
Build Your Cookies:
Roll dough into balls flatten top with pineapple and cherry.
Bake to Golden:
Let them bake until perfect cool before moving.

My Best Tips

Really drain that pineapple well we don't want soggy cookies. Chill your dough if it gets too soft. Press the topping in gently and add some holiday sprinkles for extra sparkle.

Keep Them Fresh

These beauties stay perfect for 3 days in a container or up to a week in the fridge. Want to freeze them? Layer them carefully with parchment they'll keep beautifully.

Quick Answers

  • Fresh pineapple works just drain it well
  • Brown sugar's best but honey works too
  • Make ahead? Dough chills nicely
  • Toppings sliding? Press them in gently

Sweet Holiday Joy

These cookies bring such a bright cheerful touch to holiday baking! They're easy enough for anyone to make but look so impressive on a cookie platter. Give them a try they're sure to become a new holiday favorite!

Frequently Asked Questions

→ Why drain the pineapple well?

Excess moisture can make cookies spread too much and affect texture.

→ Do I need to chill the dough?

Optional but helps with handling. 15-20 minutes is enough if dough is sticky.

→ Can I make these ahead?

Yes, store in airtight container up to 5 days. Layer with wax paper.

→ Can I freeze these cookies?

Best fresh as fruit toppings don't freeze well.

→ How do I make them more festive?

Add red and green sanding sugar before baking for holiday sparkle.

Pineapple Upside-Down Cookies

Soft sugar cookies topped with sweet pineapple and maraschino cherries. A cookie version of the classic upside-down cake perfect for Christmas.

Prep Time
15 Minutes
Cook Time
12 Minutes
Total Time
27 Minutes
By: Casey


Difficulty: Intermediate

Cuisine: American

Yield: 24 Servings (24)

Dietary: Vegetarian

Ingredients

01 1/2 cup unsalted butter, softened.
02 3/4 cup granulated sugar.
03 1 large egg.
04 1 tsp vanilla extract.
05 1 1/2 cups all-purpose flour.
06 1/2 tsp baking powder.
07 1/4 tsp salt.
08 6 maraschino cherries, halved.
09 1/4 cup crushed pineapple, well drained.
10 2 tbsp brown sugar.

Instructions

Step 01

Mix drained pineapple and brown sugar. Set aside.

Step 02

Cream butter and sugar until fluffy.

Step 03

Beat in egg and vanilla.

Step 04

Whisk dry ingredients separately.

Step 05

Gradually mix dry into wet until dough forms.

Step 06

Heat oven to 350°F. Line baking sheet.

Step 07

Roll 1-inch dough balls, place 2 inches apart.

Step 08

Flatten balls slightly.

Step 09

Top each with pineapple mixture and cherry half.

Step 10

Bake 10-12 minutes until edges golden.

Step 11

Cool 5 minutes on pan, then move to rack.

Notes

  1. Drain pineapple very well to prevent spreading.
  2. Can chill dough if too sticky.
  3. Add colored sugar for festive look.
  4. Best enjoyed fresh.

Tools You'll Need

  • Baking sheet.
  • Parchment paper.
  • Mixing bowls.
  • Electric mixer.
  • Wire rack.

Allergy Information

Please check ingredients for potential allergens and consult a health professional if in doubt.
  • Eggs.
  • Dairy.
  • Wheat/Gluten.

Nutrition Facts (Per Serving)

It is important to consider this information as approximate and not to use it as definitive health advice.
  • Calories: 110
  • Total Fat: 5 g
  • Total Carbohydrate: 16 g
  • Protein: 1 g