Pineapple Filled Cookies: the best cookies in the world

Every year, for Christmas, my grandmom would make my favorite cookie of all time, Pineapple- Filled Cookies. She would make them just for me…well, I think she must have liked them too…they weren’t a favorite among the rest of the family though. The recipe for these pie-like cookies came from her mother, my great-grandmother (who I never met). Where it came from before that, I do not know. And before she passed away, my grandmother passed the recipe onto me.

I’ve tried to make the cookies before, but I was never satisfied with the results. Part of the problem is that my grandmother’s recipe is not the easiest one to follow.  For most of the ingredients, she did not indicate how much to use. For example, her recipe calls for you to “flour accordingly”. Now, I don’t know what that means, I just want to know how much flour to use! Over the years, I’ve tried to make these cookies, using this wonky recipe, about half a dozen times to no success. I haven’t tried for a very long time, but this year, I decided I was going to figure it out.

Yesterday, I did just that. I will admit my first batch was a disaster, but the second one was just like Grandmom used to make.

Pineapple-Filled Cookies (adapted from Great-Grandmom’s Recipe)

Ingredients:

3/4 cup of non- hydrogenated vegetable shortening *
1 cup of sugar, plus one tablespoon
1 teaspoon of vanilla extract
1 egg
1/2 cup of milk *
1 can of crushed pineapple in it’s own juice, 20 oz
1 1/2 teaspoon of corn starch
1/2 teaspoon of baking soda
3 teaspoon of baking powder
3 1/2 cups of flour, plus more for rolling

* non-hydrogenated shortening is available at natural foods stores. It is much better than hydrogenated versions, better for you and better tasting. I think coconut oil (which is solid at room temperature) might be a substitute, but I have not tried this.

* regular milk or almond, which is what I used.

Directions:

1. Preferably in a stand mixer & using the paddle attachment, mix the shortening, sugar and vanilla. Then add the egg. You can use a hand mixer, but you will need to get your hands dirty a little sooner.
2. Once blended, add the milk. Don’t worry if the batter looks curdled, it’s okay.
3. If using a stand mixer, change the paddle attachment to the dough hook.
4. Sift the dry ingredients together (flour, baking soda, baking powder). Add them a cup at a time to the batter until all is incorporated.
5. Meanwhile, add the pineapple & tablespoon of sugar to a saucepan. Once the sugar has melted, add the cornstarch to thicken the pineapple. Allow to cool completely!
6. Turn the dough out onto a floured surface. Using a rolling pin, roll out the dough until it is no thicker than 1/8″. Thinner is better if you got the skills.
7. Using a round cookie cutter or a glass, cut out circles from your dough. Make sure to end up with an even number, since you need a top and a bottom for each cookie.
8. Place the bottoms onto a parchment lined cookie sheet and top each with a heaping teaspoon of thecooled pineapple mixture. Then top with another dough circle. Crimp the edges and use a fork to add some vent holes.
9. Bake at 350° F for 12 minutes or until bottoms are lightly browned.

Yields 2 dozen cookies and lasts about 2-3 days. After that they get too mushy.