Why You’ll Love This Recipe

These cookies combine a creamy, tangy pineapple cream cheese filling with a delicate almond-scented dough rolled into beautiful pinwheels. They’re not only delicious but also visually impressive—perfect for holiday gatherings or anytime you want to wow your guests without complicated baking.

Ingredients

Cookie Dough

1 cup unsalted butter, softened
1 cup granulated sugar
¾ teaspoon almond extract
1 egg, room temperature
2 ½ cups all-purpose flour
¼ teaspoon salt

Filling

20 oz crushed pineapple, well drained (juice reserved)
8 oz cream cheese, softened
⅓ cup granulated sugar

Glaze

1 cup powdered sugar
2 tablespoons pineapple juice
Sprinkles (optional)

(Tip: You’ll find the full list of ingredients and measurements in the recipe card below.)

Directions

Filling

Press out all juice from crushed pineapple, reserving the juice for glaze.
Beat cream cheese and sugar in a medium bowl until fluffy, about 2 minutes.
Mix in pineapple until combined.
Remove ½ cup of filling and set aside for serving with crackers later, if desired. Reserve the rest for the cookies.

Cookie Dough

Cream butter and sugar in a large bowl until light and fluffy.
Add almond extract and egg; mix well.
Stir in flour and salt just until incorporated.
Divide dough in half.
Cover a large cutting board with plastic wrap. Using another piece of plastic wrap, press half the dough into an 8-inch square.
Spread half the pineapple filling evenly over the dough, leaving about ½ inch around edges.
Carefully roll the dough, using plastic wrap to help. Pinch edges to seal. Wrap tightly in plastic wrap and refrigerate for 2 hours up to 48 hours.
Repeat rolling and filling with the remaining dough and filling.

Baking

Preheat oven to 350°F (175°C). Line baking sheets with parchment paper.
Slice rolls into ¼ to 3/8-inch thick slices and place on baking sheets.
Bake 10–12 minutes, until bottoms are lightly browned.
Cool on baking sheet for 1–2 minutes, then transfer to wire racks. Repeat with remaining slices.

Glaze

Whisk powdered sugar and pineapple juice until smooth.
Drizzle glaze over cooled cookies. Add sprinkles if desired while glaze is wet.
Let glaze harden before storing cookies in an airtight container.

Servings and Timing

Serves: 36 cookies
Prep time: 10 minutes
Chill time: 2 hours
Cook time: 10 minutes
Total time: Approximately 20 minutes active, plus chilling

Variations

Substitute crushed pineapple with other crushed fruits like mango or peaches for a tropical twist.
Add finely chopped toasted coconut to the filling for extra texture and flavor.
Use lemon or orange zest in the dough for a citrusy note.
Swap almond extract for vanilla extract if preferred.

Storage/Reheating

Store in an airtight container at room temperature for up to 5 days.
For longer storage, refrigerate up to a week.
The cookies are best served at room temperature.

FAQs

Can I prepare the dough and filling ahead of time?

Yes, you can refrigerate dough and filling separately for up to 2 days before assembling.

What if my filling is too runny?

Make sure to drain pineapple thoroughly. If still too wet, gently press out extra juice or add a tablespoon of powdered sugar to thicken.

Can I freeze the cookie rolls before baking?

Yes, freeze the rolled dough wrapped in plastic wrap for up to a month. Thaw before slicing and baking.

Can I use regular cream cheese or a low-fat version?

Regular cream cheese gives best texture, but low-fat can be used with slightly less creamy results.

How can I prevent the filling from leaking while baking?

Be sure to seal the edges of the dough tightly when rolling.

Can I make these gluten-free?

Yes, use a gluten-free all-purpose flour blend in place of regular flour.

What’s the best way to slice the rolls?

Use a sharp serrated knife and slice gently to avoid squishing.

Can I omit the glaze?

Yes, but the glaze adds sweetness and a nice finish.

Are these cookies suitable for kids?

Absolutely! They are sweet, creamy, and fun to eat.

Can I use canned pineapple chunks instead?

It’s best to use crushed pineapple for the right texture, but finely chopped chunks can work if drained well.

Conclusion

Pineapple Pinwheel Cookies combine creamy pineapple cheesecake filling with tender almond-scented dough rolled into beautiful spirals. With a sweet glaze finish, these festive treats are perfect for holiday celebrations or anytime you want to impress with minimal effort. Their delightful texture and bright tropical flavor will quickly make them a family favorite!