Pineapple Filled Cookies: the best cookies in the world

pineapple filled cookie recipe

Every year, for Christmas, my grandmom would make my favorite cookie of all time, Pineapple- Filled Cookies. She would make them just for me…well, I think she must have liked them too…they weren’t a favorite among the rest of the family though. The recipe for these pie-like cookies came from her mother, my great-grandmother (who I never met). Where it came from before that, I do not know. And before she passed away, my grandmother passed the recipe onto me.

I’ve tried to make the cookies before, but I was never satisfied with the results. Part of the problem is that my grandmother’s recipe is not the easiest one to follow.  For most of the ingredients, she did not indicate how much to use. For example, her recipe calls for you to “flour accordingly”. Now, I don’t know what that means, I just want to know how much flour to use! Over the years, I’ve tried to make these cookies, using this wonky recipe, about half a dozen times to no success. I haven’t tried for a very long time, but this year, I decided I was going to figure it out.

Yesterday, I did just that. I will admit my first batch was a disaster, but the second one was just like Grandmom used to make.

Pineapple-Filled Cookies (adapted from Great-Grandmom’s Recipe)

Ingredients:

3/4 cup of non- hydrogenated vegetable shortening *
1 cup of sugar, plus one tablespoon
1 teaspoon of vanilla extract
1 egg
1/2 cup of milk *
1 can of crushed pineapple in it’s own juice, 20 oz
1 1/2 teaspoon of corn starch
1/2 teaspoon of baking soda
3 teaspoon of baking powder
3 1/2 cups of flour, plus more for rolling

* non-hydrogenated shortening is available at natural foods stores. It is much better than hydrogenated versions, better for you and better tasting. I think coconut oil (which is solid at room temperature) might be a substitute, but I have not tried this.

* regular milk or almond, which is what I used.

Directions:

  1. Preferably in a stand mixer & using the paddle attachment, mix the shortening, sugar and vanilla. Then add the egg. You can use a hand mixer, but you will need to get your hands dirty a little sooner.
  2. Once blended, add the milk. Don’t worry if the batter looks curdled, it’s okay.
  3. If using a stand mixer, change the paddle attachment to the dough hook.
  4. Sift the dry ingredients together (flour, baking soda, baking powder). Add them a cup at a time to the batter until all is incorporated.
  5. Meanwhile, add the pineapple & tablespoon of sugar to a saucepan. Once the sugar has melted, add the cornstarch to thicken the pineapple. Allow to cool completely!
  6. Turn the dough out onto a floured surface. Using a rolling pin, roll out the dough until it is no thicker than 1/8″. Thinner is better if you got the skills.
  7. Using a round cookie cutter or a glass, cut out circles from your dough. Make sure to end up with an even number, since you need a top and a bottom for each cookie.
  8. Place the bottoms onto a parchment lined cookie sheet and top each with a heaping teaspoon of thecooled pineapple mixture. Then top with another dough circle. Crimp the edges and use a fork to add some vent holes.
  9. Bake at 350° F for 12 minutes or until bottoms are lightly browned.

Yields 2 dozen cookies and lasts about 2-3 days. After that they get too mushy.

pineapple filled cookie recipe

pineapple filled cookie recipe

pineapple filled cookie recipe

pineapple filled cookie recipe

pineapple filled cookie recipe

pineapple filled cookie recipe

15 thoughts on “Pineapple Filled Cookies: the best cookies in the world

  • April 21, 2012 at 7:02 pm
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    Hello,
    I am wondering if these can be frozen and defrosted, or whether they will get mushy that way too? Thanks!

  • March 13, 2012 at 10:34 am
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    This is like my grams recipe also..She makes them every year for my dads bday..Well I have sat with her many times when she has made them..This is much easier ove it.. thank you

  • December 19, 2011 at 2:56 pm
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    These cookies look delicious! The pictures are awesome also! Come by the USPS Facebook page and join the holiday conversation by sharing this unique recipe! http://on.fb.me/ujGGtE

  • December 14, 2011 at 5:37 am
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    I have a great recipe for these – they are amazing – in lieu of crushed pineappe its pinapple preserves which is little easier to work with. (not as runny). they come amazing but are a lot of work. Email if youw ant that recipe.

  • February 2, 2011 at 11:01 am
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    I’m glad you all like the sound of these cookies. Please share if you end of up making them, I’d love to hear what you think.

  • January 27, 2011 at 5:58 pm
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    These sound delicious. I am going to have to try them out.

  • January 26, 2011 at 5:34 am
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    Wow! These look amazing! Kind of like fruit mince pies, I am thinking? I was just wondering what you meant when you said “regular milk or almond” – what is almond milk? Where do you get it/how is it made?

  • January 26, 2011 at 3:46 am
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    YUM. I put strawberry jam inside some of these too! My bf wants to try pb and jelly next time 🙂 Thanks for the recipe!

  • January 24, 2011 at 10:18 pm
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    Oh baby. Oh yeah baby. These look sooo goood. MMmmm. Oh yeah. Oh yeah.

    Thank you so much for the recipe.

  • January 20, 2011 at 7:02 am
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    A very different recipe! Here in Brazil we use guava. I’ll try.

    =D

  • January 16, 2011 at 4:21 am
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    These look incredibly delicious! I can’t wait to try them. Thanks for sharing the recipe.

  • January 16, 2011 at 3:31 am
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    What a fabulous-looking recipe! Found you from Craft: Daily and I’m so glad they led me here. I need to try these right away. Thanks!

  • January 15, 2011 at 8:29 pm
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    I think just using a piecrust recipe or a defrosted froze piecrust would work perfectly, any type of filling used for a pie is perfect for the recipe. apple, cherry, etc. the cookies are really teeny weeny pies. Different shaped cookie cutters could also do the job.

  • January 15, 2011 at 7:29 pm
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    Thank you so much for this recipe! My kids are pineapple FANATICS and I can’t wait to make this for them !!

  • January 14, 2011 at 10:13 am
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    I love pineapple,I love grandmother recipes – better yet a great one! These would also taste lovely with the addition of some minced crystallized ginger and/or some bitter chocolate!

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