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Pineapple Upside-down Cookies

A friend of mine had a birthday coming up and made a special request, a challenge... pineapple upside-down cookies.  I scoured the internet for a recipe and with no success, I set out to create one on my own.  After a couple of less than delectable attempts, I came up with this recipe.  I have to admit, it's one of my favorite.  It's a rich and unique cookie that won't fail to satisfy your craving for the taste of pineapple upside-down cake...in a cookie!


Ingredients
Pineapple Upside-down Cookies...inspired by Nicole
1½  cups (3 sticks) butter, softened
2     cups brown sugar, packed
1     teaspoon vanilla
3½  cups all-purpose flour
¼    teaspoon kosher salt
1     can (20oz) crushed pineapple

Directions
Preheat oven to 350 degrees F.

For the filling:
Combine pineapple (with the juice) and 1 cup of the brown sugar in a saucepan.  Bring to a boil over medium-high heat.  Reduce heat and simmer until liquid thickens (about 20 minutes).  Remove from heat and separate pineapple from syrup and allow both to cool. 

For cookies:
Cream together the butter and the remaining brown sugar until they are just combined and then add vanilla.  Sift together the flour and salt.  With the mixer on low speed, add the flour mixture into the creamed butter and sugar.  Mix until the dough starts to come together.  Dump onto a floured board and roll together into a flat disk.  Wrap in waxed paper and chill for 30 minutes.

Roll the dough into 1 1/4-inch balls.  Place the balls on an ungreased sheet and press a slight indention into the top of each with our thumb.  Drop 1/2 teaspoon of pineapple filling into each indentation.  Bake for 20-25 minutes, until golden brown.  Brush  pineapple syrup over the hot cookies.  Cool and serve.

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