Filled Cookies

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My extended family enjoys these pineapple raisin filled cookies every year on Christmas. It’s such a delicious family recipe!

These filled cookies are a Christmas tradition in my family. It's a fun holiday dessert recipe to make with kids. Everyone loves these fruity cookies!

I feel a little guilty about making these cookies in November.

Filled cookies have been a Christmas tradition in my husband’s family for decades. We’ve never eaten them outside of the Christmas season. They’re sacredly enjoyed in late December.

These cookies are a special treat that all my in-laws look forward to at Christmastime. Some of our relatives make them a little smaller, some prefer extra filling, and others like the dough to be rolled out extra thin. We all have opinions about these cookies.

Pineapple raisin filling cooling in the pot

Pineapple Raisin Filled Cookies

When my husband and I were first married, we often visited his parents in Vermont on or around Christmas. One thing we could always count on during those visits were giant tins of cookies. There would be a big batch of chocolate chip cookies and a big batch of these pineapple and raisin filled cookies. It was always a hard decision between the two.

I love holiday traditions, especially when cookies are involved.

This recipe originated with my husband’s grandmother, and the cookies are delicious just the way she made them. It’s a rare use of white sugar on my blog, but you can substitute pure maple syrup if you’d like to try a real food version.

These cookies are a delicious dessert for Christmas or any time of year!

I did adjust great-grandma’s recipe to make the cookies gluten-free and dairy-free to accommodate food sensitivities in my family. If you want to try these delicious cookies for the holidays, feel free to substitute wheat and dairy ingredients for the coconut oil, coconut milk, and gluten-free flour if you prefer. You’ll love them either way!

These filled cookies are a classic Christmas dessert recipe. So good!

Filled Cookies

These filled cookies are a Christmas tradition in my family. It's a fun holiday dessert recipe.
Print Recipe
5 from 11 votes
Filled cookies in a stack
Prep Time:30 minutes
Cook Time:45 minutes
Total Time:1 hour 15 minutes


Ingredients for the Dough

  • 1/2 cup melted coconut oil
  • 1 cup sugar
  • 1 egg
  • 1/2 tsp vanilla extract
  • 3 1/2 cups gluten-free flour
  • 1 tsp baking soda
  • 1 tsp cream of tartar
  • 1/2 cup coconut milk

Ingredients for the Filling

  • 1 cup golden raisins
  • 20 ounces crushed pineapple with juice
  • 3/4 cup sugar
  • 2 tbs tapioca starch or other starch
  • 1/2 cup water


  • Preheat the oven to 375 degrees.
  • Melt the coconut oil, and let it cool to room temperature.
  • In the bowl of a stand mixer, mix the cooled coconut oil, sugar, egg, and vanilla extract until well-combined.
  • In a separate bowl, stir together the flour, baking soda, and cream of tartar. Add this dry mixture to the wet ingredients a little bit at a time, alternating with the milk. Start and end with a portion of the dry ingredients (i.e. dry, milk, dry, milk, dry). Form the dough into two balls. Wrap each ball in a piece of wax paper and refrigerate briefly while you prepare the filling ingredients. (If you refrigerate it for too long, the coconut oil will solidify and the dough will become too hard to handle.)
  • To make the filling, combine the raisins, crushed pineapple, and sugar in a small saucepan. Bring to a slight boil. While this mixture is heating up, stir together the starch and the water in a small bowl. Add it to the boiling filling mixture, and stir to thicken. You’ll need to stir the lightly boiling mixture for a minute or two until it’s no longer runny.
  • Remove the dough from the refrigerator and roll it out to about 1/8 inch thickness (as thin as possible) on a well-floured surface. Cut out 3-inch circles of dough using a cookie cutter or a glass.
  • Put 9 circles of dough on a cookie sheet, and place about two teaspoons of filling in the middle of each circle. Then place another circle on top of the filling and press down the edges.
  • Bake for 10 to 12 minutes, until lightly browned.

Approximate Nutrition Info

Calories: 255kcal | Carbohydrates: 49g | Protein: 3g | Fat: 7g | Saturated Fat: 5g | Polyunsaturated Fat: 0.3g | Monounsaturated Fat: 1g | Trans Fat: 0.001g | Cholesterol: 9mg | Sodium: 66mg | Potassium: 131mg | Fiber: 3g | Sugar: 30g | Vitamin A: 29IU | Vitamin C: 3mg | Calcium: 29mg | Iron: 1mg
Servings: 18
Calories: 255kcal
Cost: $.46 per serving

This recipe may contain affiliate links. A purchase or click through one of these links may result in a commission paid to us at no additional cost to you.

Price Breakdown

This recipe costs a total of $8.14, or $.23 per cookie. These filled cookies are such a fun holiday tradition in my family!

Here are more healthy Christmas cookies to enjoy during the holiday season.

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  1. 5 stars
    These little cookies look so cute!!! Almost like an apple pie. I would love to make these for my family. I am pinning to try this weekend.

  2. 5 stars
    I’ve never made filled cookies, but have loved receiving them during the holidays. This recipe sounds delicious, can’t wait to make it!

  3. I have been looking high and low for my grandmother’s mincemeat filled cookie recipe for many years. This is the closest I’ve seen! My grandmother’s cookies were soft and you don’t mention if yours are soft or crunchy, but I’m going to try them!

  4. My mother-in-law used to make a filled cookie similar to this one, but she filled hers with dates. Your raisin pineapple filling sounds wonderful.

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