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Pineapple Cookies

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Light and flaky pastry rounds with juicy pineapple filling, topped with maraschino cherries, pecans, and powdered sugar glaze. These pretty pineapple cookies will make you feel like a top pastry chef. 

Pineapple Cookies, light flaky pastry rounds with juicy pineapple filling, topped with maraschino cherries, pecans, and powdered sugar glaze.

Pineapple Cookies

Do you watch any reality tv shows?

I watch a few food competition shows, but that’s about it. Well this past weekend at Go Blog Social KC I had the opportunity to meet a reality tv star. Kind of exciting, right? One of the speakers at the conference was Jade Roper Tolbert. Jade was a contestant on the show The Bachelor and then was on The Bachelor in Paradise.  After listening to her speak I have to tell you guys, I don’t think I’d make it in the reality tv world. I’d be the one crying asking to go home because I missed my family! True story, I really would.


Pineapple Cookies

You know, there was a call not that long ago for submissions for the American version of my favorite cooking competition show: The Great British Bakeoff.

I really thought about applying to be on the show. But I didn’t put in a submission for that same reason, I just don’t think I could be away from my kids that long.  However, that doesn’t stop me from absolutely loving the show and dreaming of being on it. How about you, if you had the chance would you join a reality tv show and if so, which one?

Pineapple Cookies

While making these pineapple and maraschino cherry filled cookies, I couldn’t help but think of the contestants on the Great British Bakeoff.  If I was going to be in a bakeoff I think I’d make these cookies. They do take some time to make, but they are so so gorgeous when they are finished.  The base is a sweet flaky pastry round which is topped with pineapple jam and maraschino cherry. Piping on the final swirls of glaze onto each bright cookie I felt just like a pastry chef and couldn’t help but imagine Mary Berry telling me me that it was a delightful bake!

These cookies have many steps, so make sure you read through the recipe first. If you have a hard time finding pineapple jam, check out my easy 20 minute Pineapple Jam recipe.   And to make the drizzling easy, I recommend spooning the glaze into a plastic baggy and snipping the end off to make sure the glaze gets just where you want it!

I hope that you enjoy these pineapple cookies and you’ll have to let me know what you think, would they be worthy of Mary Berry’s praise or would she send me packing?

Pineapple Cookies

Pineapple Cookies

Yield: 3 dozen
Prep Time: 3 hours 45 minutes
Cook Time: 15 minutes
Total Time: 4 hours

Light and flaky pastry rounds with juicy pineapple filling, topped with maraschino cherries, pecans, and powdered sugar glaze.


  • 1 1/2 cups unbleached all-purpose flour
  • 1 cup butter
  • 1/2 cup sour cream
  • 3 Tablespoons light brown sugar
  • 3 Tablespoons sugar
  • 1/2 cup pineapple jam
  • 1/2 jar maraschino cherries, , chopped into halves
  • 1/4 cup finely chopped pecan pieces
  • Glaze:
  • 1/2 cup sifted confectioners sugar
  • 1 1/2 teaspoon milk


  1. In a medium sized mixing bowl, blend together the flour, butter, sour cream and brown sugar until thoroughly combined. Dough will be stiff. Divide dough in half. Cover and chill for 3 hours in the refrigerator.
  2. Preheat the oven to 350 degrees.
  3. Lightly flour your working surface, then roll out each half of the dough to a 1/8 inch thickness. Using a 2 inch round cookie cutter, cut the dough into rounds.
  4. Then using a 1 inch round cutter, cut out the centers from half of the rounds.
  5. Lightly brush water over the cookies with the holes cut in them, then place them wet side down on top of the cookies without the holes.
  6. Place the cookies 1 inch apart on ungreased baking sheets.
  7. Combine the 3 Tablespoons of sugar with 1 Tablespoon of water and using a pastry brush, brush the tops of the cookies.
  8. Spoon 1/2 teaspoon pineapple jam into the center of each cookie then place one half a maraschino cherry over the pineapple jam in the center.
  9. Sprinkle the cookies with the chopped pecans.
  10. Bake the cookies at 350 degrees for 15 to 20 minutes or until the edges are lightly browned.
  11. Cool completely on a wire rack.
  12. Mix together 1/2 cup sifted confectioners sugar with milk until the the icing is smooth and of a drizzling consistency.
  13. Drizzle icing over the tops of the cookies and serve.

Did you make this recipe?

Please leave a review or a photo! I'd love to hear your feedback!




Laura @MotherWouldKnow

Friday 11th of March 2016

What pretty little treasures! I love that your filling is done with your own homemade version of jam.

Recipes @ Globe Scoffers

Wednesday 9th of March 2016

These cookies are beautiful! Can't wait to try them. ?

Bella B (xoxoBella)

Tuesday 8th of March 2016

I pinned these. They look amazing!

Amy D

Tuesday 8th of March 2016

Oh, thanks so much Bella!

Debi at Life Currents

Tuesday 8th of March 2016

I think these are so cute! I love that you made the cookie too, and didn't use a premade dough. That pineapple jam is calling my name. Off to check the recipe!

Sophia- Veggies Don't Bite

Tuesday 8th of March 2016

I love pineapple! And pecans. What a unique cookie recipe!

Amy D

Tuesday 8th of March 2016

They are definitely a little different than most, but I think in a good way. Hopefully other people will too. :)

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