Pineapple Pinwheel Cookies - Mom On Timeout

Wonderfully easy and festive, these Pineapple Pinwheel Cookies are the showstoppers you’ve been looking for! The pineapple cheesecake filling is perfectly matched by the simple and sweet almond flavored cookie dough and is sure to be a hit with friends and family this year! Cookies are LIFE. Make sure to try these Almond Joy Cookies, Cranberry Orange Shortbread Cookies, and Peppermint Snowball Cookies!

This post is sponsored by Dole Packaged Foods.

Pineapple Pinwheel Cookies

Without a doubt it is that time of year that we all know and love: COOKIE SEASON! I could literally eat cookies every single day during the holiday season and never get sick of them.

I’ve found that the trick is to make a good variety of cookies. All chewy ginger cookies or snowball cookies can get boring after a time. I am loving these Pinwheel Pineapple Cookies for SO many reasons and one is that they are a bit unexpected yet wonderfully festive.

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With the holiday season upon us, the number of recipes on our “must-make Christmas cookie list” continues to grow. The good news is that these pinwheel cookies will be one of the easiest cookies you make all season long and the one you’ll keep coming back to again and again, even after the holiday season has passed.

These festive cookies are so pretty and totally irresistible with a pineapple cream cheese filling that will make you go WOW.

I used my favorite pinwheel cookie base (I love pinwheels everything…) that I have used over and over and over again because it’s just that good. I use my mom’s secret ingredient – almond extract – for the most amazing flavor EVER. The cookie dough is super easy to make and doesn’t even have to be chilled before rolling out.

Now, you do need to chill the dough after rolling to firm up the dough so you can cut nice, clean slices.

What Do I Need To Make Pinwheel Cookies

For the cookie dough:

• flour
• sugar
• butter
• egg
• almond extract

The filling is just three ingredients:

The trick to the filling is to really drain the Dole crushed pineapple well. You want to press all the juice out so give it some time. I usually start with the pineapple and then work on the cookie dough, intermittently coming back over to press out as much juice as possible. (Save that juice and make some pineapple punch or just give it to the kids to drink – mine LOVE it!)

The pineapple gets mixed together with the cream cheese and sugar creating a pineapple cheesecake type filling. It gets spread over the cookie dough and rolled up like a cinnamon roll or sushi.

Now, the glaze and sprinkles are entirely optional but I love how pretty these cookies look with that added touch. The glaze is just pineapple juice and powdered sugar and takes about 2 seconds to pull together. Soooo, DO IT.

Why Use Almond Extract

• Almond extract is clear, so when you’re making cookies that are supposed to white or very light in color, it really works best.
• The flavor is a little unexpected. We are so used to vanilla extract in our cookie recipes that the almond really makes you sit up and take notice.
• If you can’t find almond extract, or prefer vanilla, feel free to use that instead. A clear vanilla extract will keep the cookies lighter in color.
• I’ll admit, I was a little skeptical that almond and pineapple would work together. Guess what? It’s straight up delicious.

Reece came home from school and promptly walked into the kitchen to see what I was making. He took a quick bite and started walking out of the kitchen, turned around, and grabbed two more cookies to go. He told me later they were the BEST cookies he’s ever had. That says a lot. You guys know how many cookies I’ve made lol!

More Pineapple Desserts to Try

How To Make Pineapple Pinwheel Cookies

Pineapple Pinwheel Cookies

Wonderfully easy and festive, these Pineapple Pinwheel Cookies are the showstoppers you've been looking for! The pineapple cheesecake filling is perfectly matched by the simple and sweet almond flavored cookie dough and is sure to be a hit with friends and family this year! 

Ingredients

Cookie Dough

• 1 cup unsalted butter softened
• 1 cup granulated sugar
• ¾ tsp almond extract
• 1 egg room temperature
• 2 ½ cups all-purpose flour
• 1/4 tsp salt

Filling

• 20 oz crushed pineapple well drained, juice reserved
• 8 oz cream cheese softened
• 1/3 cup granulated sugar

Glaze

• 1 cup powdered sugar
• 2 tbsp pineapple juice
• sprinkles optional

Instructions

Filling

• Make sure all of the juice has been pressed out of the pineapple (reserving juice for glaze). Combine cream cheese and sugar in a medium bowl and beat until fluffy and combined, about 2 minutes.

• Add the pineapple and mix until combined. Remove 1/2 cup of filling and save to serve with crackers later. Set aside remaining filling.

Cookie Dough

• Cream butter and sugar together in a large mixing bowl. Mix in the almond extract and egg until well combined. 

• Stir in the flour, mixing just until incorporated.

• Divide the dough in half.

• Cover a large cutting board with plastic wrap and use another piece of plastic wrap to press out half of the dough into an 8-inch square.

• Spread half of filling over the dough to within half an inch of the edges.

• Use the plastic wrap to carefully roll up the dough.

• Pinch the edges of the dough to seal. Wrap tightly in plastic wrap and refrigerate for 2 hours up to 48 hours, or until dough is firm. (Repeat with remaining dough and filling.)

• Preheat the oven to 350 degrees F. Line a large baking sheet with parchment paper and set aside.

• Cut ¼ inch to 3/8 inch slices from the roll and place on the baking sheet. Bake for 10 to 12 minutes or until the bottoms of the cookies are very lightly browned.

• Let cool on the baking sheet for 1 to 2 minutes before moving to a wire rack. Repeat for remaining cookies.

Glaze

• Combine powdered sugar and pineapple juice in a small bowl and whisk until combined. Drizzle over the top of cooled cookies.

• Add sprinkles if desired while glaze is still wet. Let glaze harden before storing in an airtight container.

Nutrition

Calories: 151kcal | Carbohydrates: 20g | Protein: 1g | Fat: 7g | Saturated Fat: 4g | Cholesterol: 25mg | Sodium: 23mg | Potassium: 41mg | Sugar: 13g | Vitamin A: 255IU | Vitamin C: 1.6mg | Calcium: 12mg | Iron: 0.5mg

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