Pineapple Squares Recipe (2024)

A delicious Pineapple dessert recipe from my grandmother, who made these Pineapple Squares for many, many years. Combine the fresh taste of crushed pineapple in a flaky, tender crust with a sweet, creamy frosting for a wonderful, unique, Pineapple Squares Recipe.

Pineapple Squares Recipe

My grandmother made this recipe for so many functions when we were growing up! I have no idea where the recipe came from (she passed away over 25 years ago, so I cannot ask her), but I can tell you I have never seen this particular recipe online. And I looked. I wanted to make it a few years ago, and swore I had it in my recipe file. When I could not find it, I went on an internet search that led nowhere fast. I finally called my niece who sent me pictures of her copy of the recipe.

My grandmother was a hoot for directions. Ever speak to someone who was born 100 (or so) years ago about a recipe? It was always “little bit” of this, or “that much” while they pointed to their palms. As you can see the “enough milk for consistency” is straight from that mold, and what are in my grandmother’s directions.

I do have to say that this is fabulous when well chilled! It almost changes texture and taste, making the leftovers better than the fresh Pineapple Squares. If you can, refrigerate the entire dessert before cutting. While not necessary for the finished product, it will taste even better cold!

Tips for Making Pineapple Squares Recipe

● Do not get overly concerned about rolling the dough as one solid piece. What I do is make it fit in the jelly roll pan, and then if holes or tears form, pinch the dough together to close them.

● Your baked pineapple square pastry need to be completely cooled before frosting.

● For my UK and Australian friends: confectioners sugar is icing sugar (powdered sugar, 10x).

● Make certain the cream cheese for your frosting is at room temperature.

● If at all possible, refrigerate before serving. It takes far better when cold!

● Interested in making your own vanilla extract? Click here to learn how to make vanilla extract!

● For more delicious dessert recipes try this Strawberry Jello Poke Cake Recipe or this terrific Orange Creamsicle Cake Recipe

Pineapple Squares Recipe Ingredients:

Pineapple Squares Recipe Crust Ingredients:

● 4½ cups Flour
● 1¼ tsp Salt
● 1¾ cups Shortening
● 1 cup Cold Milk

Pineapple Squares Recipe Filling Ingredients:

● 2 cans Crushed Pineapple (20oz)
● 7 TBSP Tapioca
● 1 cup Sugar

Pineapple Squares Recipe Frosting Ingredients:

● 8 oz Cream Cheese, at room temperature
● 4 TBSP Butter, softened
● 3 Cups Confectioners Sugar (1 lb)
● 1 tsp Vanilla
● 1 TBSP Milk (enough milk to make for the desired consistency)
● Chopped walnuts or cut up maraschino cherries for garnish.

Pineapple Squares Mise en Place:

● Measuring Cup
● Measuring Spoons
● Pastry Cutter
● Bowls
● Jelly Roll Pan (10×15)
● Rolling Pin
● Spatula
● Stand Mixer, bowl and beaters.

Pineapple Squares Recipe Directions:

1. Preheat oven to 350°.

2. Combine flour and salt, cut in shortening.

3. Add cold milk to the crust, combine to make a crust (as you would a pie crust).

4. Divide crust dough into two balls.

5. Roll one crust ball very thin so you have a large enough piece to fit into a 15″x 10″ jelly roll pan.

6. Place that one crust into the jelly roll pan. Make sure it covers the whole pan and up the sides with enough leftover for later crimping. Set aside.

7. Combine together 2 cans crushed pineapple, 7 tablespoons of tapioca and 1 cup of sugar to make the filling.

8. Pour the pineapple mixture into the prepared crust in the jelly roll pan.

9. Roll out the second ball of dough, cover the pineapple mixture in the pan, and crimp the edges.

10. Bake in a preheated 350° oven for 45 minutes (to an hour). You want your crust LIGHTLY browned on the edges.
11. Allow to cool completely before frosting.

12. To make the frosting combine the room temperature cream cheese and butter in a mixing bowl. Beat on low until combined. Slowly add your confectioner’s sugar, alternating with cold milk. I wrote down 1 TBSP of cold milk, but unless your cream cheese is very wet, you will probably need a tad more to get a smooth and creamy frosting. My Grandmother’s directions are actually: “* enough milk for desired consistency.”

13. Frost pineapple squares when completely cool.

14. Top frosting with chopped walnuts or maraschino cherry pieces.

15. Note: this is FAR better when cold. I would suggest chilling before serving. The leftovers are astonishingly good!
16. Refrigerate leftovers.

● For more Recipes on Ann’s Entitled Life, click here.

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