Aunt Gerry’s Pineapple Cookies

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My Dad is one of 10 children in his family.  As the story goes, he was purely spoiled by his older sister, Gerry.  She coddled him, carried him and catered to him.  And he was ornery.  He and his brothers once cut the middle out of a cake she made.  They spread icing back over the hole so that no one knew until the cake was cut into.

For some unknown reason, she let him live.  Not only that, but she occassionally baked up a batch of his favorite Pineapple Cookies.

Here’s what you’ll need:


1 cup butter

1 cup brown sugar

1 cup white sugar

2 eggs

20 oz can crushed pineapple, drained and juice reserved

1 tsp. vanilla

4 cups flour

1/2 tsp. salt

1 1/2 tsp. baking soda

1/2 tsp. baking powder

For the icing:

reserved pineapple juice

2 cups powdered sugar

I didn’t have any crushed pineapple, so I ran a can of pineapple chunks through the blender.  It worked, but crushed is better.

Iin a mixer bowl cream the butter with the sugars.  Add the eggs, pineapple and vanilla.  In a large bowl, combine the dry ingredients.  Blend into the wet ingredients.  Drop by teaspoonful onto a greased cookie sheet.  Bake at 400 degrees for 8-10 minutes.

For the icing: Gradually add pineapple juice to the powdered sugar by the tablespoon.  You want the consistency to be a bit thick, but still stream off the spoon.  While the cookies are still warm, spread the icing on the tops.

This recipe makes about 8 dozen soft, delicious cookies.

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  1. Okay, so I’m a chocolate-holic, but I think these would be divine with a chocolate drizzle, and some fresh coconut on top! Thanks for the great recipe!

  2. My husband would love these. He is a pineapple anything freak. Thanks for sharing.

  3. Mmmmm….I’ve not made cookies with pineapple. This sounds great.

  4. My husband’s favorite dessert of all time is pineapple upside-down cake, so I think these cookies would be right up his alley. I can’t wait to surprise him with a batch of these treats! Thanks for sharing!

  5. I have been searching for this lost recipe for a long time, my husband loves pineapple upside down cake and I’m sure he will love these too. I made these several years ago and then lost the recipe during one of our moves. Thanks!

  6. Oh these look delicious, thanks for sharing!

  7. sugar plum says:

    Lovely site-landed here looking for pineaaple cookies that my taste buds are demanding for quite awhile.lovely blog u have here.

  8. Can margarine be used instead of butter?

  9. I made these Sunday for our Life Group and they were a hit….I actually made 3 variations….1 baked one pan as you show…..than I added coconut to the next batch and then I also added white chocolate chips….all 3 ways were really good!!!! Nice moist cookie 🙂 Batter is really good too!!!!


  10. These are fabulous! Everyone loves them– They have become the “go-to” cookie!!

  11. Sharon Williams says:

    These cookies are good even without icing. All i do is stick a cherry in center. We don’t like sicky sweet and these aren’t. Excellent receipe. Tried many and this one is the BEST.


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