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Italian Pineapple Cookies

These popular cookies are made many different ways depending on where in Italy you get the recipe. This is a recipe from a friend of mine whose mother-in-law was Sicilian.
Prep Time1 hour
Cook Time20 minutes
Course: Dessert
Cuisine: Italian
Servings: 40

Ingredients

Dough

  • 6 cups all purpose flour (this original recipe asked for Robin Hood flour)
  • 2 cups butter or margarine, melted (this original recipe asked for Blue Bonnet Imperial margarine - I used butter)
  • 1 pkg instant yeast (about 2 1/2 tsp)
  • 1/2 cup warm (100 degrees) water
  • 2 tbsp sugar
  • 4 large eggs beaten
  • 1 pkg Vanillin powder (available at Italian grocers) or sub in 1 tsp vanilla

Pineapple Jam Filling:

  • 3 cans (540mL/19 fl oz) crushed pineapple drained (reserve juice)
  • 1 1/2 cups sugar
  • 1/4 cup cornstarch

To finish:

  • icing sugar for rolling and dusting

Instructions

  • In a medium saucepan, add drained, crushed pineapple and sugar and cook over medium heat until thickened (depending on your stove, it may take up to 30-45 minutes - just be careful to not burn it)
  • While the mixture is cooking, place cornstarch in a small bowl and add in about 2 tablespoons of the reserved pineapple juice and mix until the cornstarch is blended (you can freeze the pineapple juice to use later in a cocktail or to marinate chicken)
  • At about the 20 minute mark, add the cornstarch mixture and continue cooking.
  • Place jam mixture covered, in the refrigerator (or cool space like a cellar) overnight if possible.
  • In a small cup, add warm water, yeast and sugar and stir well; set aside to wait for the yeast to 'bloom' (if the yeast doesn't get 'puffy', it's probably not active anymore).
  • On a clean countertop or a very large bowl (I used my largest stainless steel bowl), mix together all the dry (dough) ingredients; make a well/hole in the centre of the dry ingredients and add yeast mixture, beaten eggs and vanilla into the well. Mix the wet ingredients together gently and then begin to incorporate the dry ingredients until it all comes together to form a dough (though dough will seem very greasy...that's okay)
  • If you can, cover the dough with plastic wrap and place in the fridge overnight (if you don't have the time, place in the freezer for 15-20 minutes).
  • When you are ready to assemble the cookies, take out the dough and dust your countertop with icing sugar (do not use flour...see NOTES); divide the dough into 16 pieces.
  • Preheat oven to 350 as you prepare the cookies; Line a baking sheet with either a Silpat mat or parchment paper.
  • Beginning with one of the 16 pieces, roll out the dough into a circular shape (ensure you use enough icing sugar to make sure the dough doesn't stick) and with a pastry cutter, cut it into 12 pieces; spoon out about 1 tsp of the jam onto the large end of each triangle (see photo above) and roll inward. To ensure the the pineapple jam doesn't seep out, gently fold in the edges (see photo above).
  • Place the finished cookies onto the baking sheet and bake for 15 minutes, checking the bottom of the cookies to ensure they don't get too browned (if your oven tends to burn cookies on the bottom, double stack your cookie sheets). Bake until the tops just begin to brown (it's hardly noticeable).
  • Store them in a sealed container and use within 5-7 days. You can also freeze the baked cookies in an air-tight container - or freeze the dough and jam (separately) and bake them later.

Notes

It's not mandatory, but the cookies will turnout better if the dough and jam are made the day/night before and allowed to sit.
Do NOT use flour to roll the cookies out...the dough has very little sugar o this adds sweetness to the dough and ensures the dough is tender.
You can also freeze the dough and jam (separately) and bake them later (or bake half and freeze half).