Step 1

Preheat oven to 350°F.

Step 2

Combine flour and salt, cut in shortening.

Step 3

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

Step 4

Divide crust dough into two balls.

Step 5

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

Step 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.

Step 7

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

Step 8

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

Step 9

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

Step 10

Bake in a preheated 350°F oven for 45 minutes (to an hour). You want your crust LIGHTLY browned on the edges.

Step 11

Allow to cool completely before frosting.

Step 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."

Step 13

Frost pineapple squares when completely cool.

Step 14

Top frosting with chopped walnuts or maraschino cherry pieces.

Step 15

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

Step 16

Refrigerate leftovers.