Popular Italian Pineapple Cookies

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Popular Italian Pineapple Cookies

As the holidays approach this year, I’m getting a bit nostalgic and when that happens, I search the internet for nostalgic desserts! These popular Italian pineapple cookies came across in my feed and reminded me that I’ve been meaning to make them for a really long time! My sister-in-laws sister-in-law’s mother-in-law (what a mouthful!!) used to make these every holiday season and I finally got a hold of the recipe!!!

There are many cookies out there that are similar but not really the same (for example, these pinch cookies by An Italian in my Kitchen just say ‘jam’ and I think it’s the pineapple that make these cookies extra special – although some people fill them with Nutella too).

I thought they would be like my rugelach cookies (you can find that recipe here) but these popular Italian pineapple cookies are made with a dough that has a higher amount of fat.

There is a similarity to my rugelach cookies in that it you roll the cookie dough out the same way and roll them once they’re filled

Popular Italian Pineapple Cookies
Popular Italian Pineapple Cookies

You can see how similar they look even after they’ve been rolled…

Popular Italian Pineapple Cookies
Popular Italian Pineapple Cookies

I was told by a friend who follows me to tuck in the edges to make sure the filling doesn’t ooze out (funny note here: her dad use to be the guy that was the “filler” of the cookies and he was eventually “fired” because he wasn’t doing a good enough job since the filling always came out during baking!!). I think my family has used that method to get out of chores ON PURPOSE ;).

Popular Italian Pineapple Cookies
Popular Italian Pineapple Cookies

You can see how beautiful and pillowy they are!! Such a nice and tender dough!!

Popular Italian Pineapple Cookies

Of course you can add any filling if you don’t feel like making the jam filling – although I feel like the jam is the star of the show!!

Popular Italian Pineapple Cookies
Let’s make sure you have all of the ingredients for these Popular Italian Pineapple Cookies:
  • flour (Robin Hood is what is recommended)
  • yeast
  • vanilla powder (purists will say you need this but you can use vanilla)
  • margarine or butter (I used butter but it was recommended to use Imperial Blue Bonnet margarine)
  • sugar
  • eggs
  • crushed pineapple
  • cornstarch
  • icing sugar

Most of these ingredients can be found at your local grocer!

Popular Italian Pineapple Cookies
Here are a few notes you need to know about these Popular Italian Pineapple Cookies:
  • 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 so this adds sweetness to the dough and ensures the dough is tender. If you use flour, the dough will be tough.
  • You can also freeze the dough and jam (separately) and bake them later (or bake half and freeze half).

You can see (below) that I am a fan of freezing dough and baking them fresh – although I know most people like to get the mess out of the way and bake them all. You do you!! I like to wrap the dough in disks and separate the jam in the same number of small freezer pouches so that you can make them a few at a time from the freezer!

Popular Italian Pineapple Cookies

Whenever we talk about nostalgic baking these cookies inevitably come up in the conversation. They are made by so many women I know (usually coming with directions from their grandmothers). Many people have different variations – some people make the cookies long and thin like a cigar, while some people make sure the dough is really thin (in which case you will come out with many more cookies – which isn’t a bad thing).

Whatever your method, I think you should try these. The sweetness of the pineapple is such a great addition to an ‘unsweet’ cookie dough – and the jam and pastry come together in one glorious and delicious bite!!

Try them out and let me know!!!!

Popular Italian Pineapple Cookies

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 Time 1 hr
Cook Time 20 mins
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).