Pineapple Cookies & Pineapple Squares (2 Recipes)
This page pairs two vintage pineapple favorites made with canned crushed pineapple: soft Pineapple Cookies and classic Pineapple Squares with an oatmeal crumble topping. Both are simple, pantry-friendly recipes with straightforward steps and familiar bake times.
Use the jump links below to go straight to the cookies or the bar-style squares—then finish with a quick pineapple baking FAQ at the bottom.
Recipes on this page
Pineapple Cookies
Ingredients
- 1 cup brown sugar
- 1 cup white sugar
- 1 cup shortening
- 2 eggs
- 1 can crushed pineapple
- 1 1/2 teaspoons vanilla
- 4 cups flour
- 1/2 teaspoon salt
- 1 1/2 teaspoons baking soda
- 1/2 teaspoon baking powder
Instructions
- Preheat oven to 350°F. Line or lightly grease a cookie sheet.
- Stir vanilla into crushed pineapple.
- Cream shortening with brown sugar and white sugar. Beat in eggs.
- Add pineapple mixture and stir until well blended.
- In a separate bowl, sift together flour, salt, baking soda, and baking powder.
- Gradually stir dry ingredients into batter.
- Drop by spoonfuls onto an ungreased cookie sheet.
- Bake 12–15 minutes, until edges are set and lightly golden. Cool briefly before removing.
Total bake time: 12–15 minutes
Equipment: cookie sheet
Servings: about 3 dozen cookies
Pineapple Squares
Ingredients
- 1 can crushed pineapple
- 1/4 cup sugar
- 1 tablespoon cornstarch
- 1 teaspoon lemon juice
- 1 cup flour
- 1/2 teaspoon salt
- 1 cup brown sugar
- 2 cups oatmeal
- 1 cup Crisco
- Confectioners’ sugar (for topping)
Instructions
- Preheat oven to 350°F. Grease a 7 1/2 x 7 1/2-inch square pan.
- In a saucepan, combine crushed pineapple, sugar, cornstarch, and lemon juice. Bring to a boil and cook until thickened and clear. Set aside.
- In a bowl, mix flour, salt, brown sugar, oatmeal, and Crisco until crumbly.
- Press half of the crumb mixture into the prepared pan.
- Spread pineapple filling over the base, then sprinkle remaining crumbs on top.
- Bake 30–35 minutes. Cool, dust with confectioners’ sugar, and cut into squares.
Variation: Substitute cherry pie filling for pineapple. Serve warm with ice cream.
Total bake time: 30–35 minutes
Equipment: 7 1/2 x 7 1/2-inch pan
Servings: 16 squares
Pineapple Cookies & Squares FAQ
Do I need to drain crushed pineapple?
No. Use crushed pineapple with its juice unless otherwise stated. The liquid adds moisture and flavor.
How do I know when pineapple cookies are done?
They’re done when edges are lightly golden and centers no longer look wet.
Can I substitute fresh pineapple?
Canned crushed pineapple works best because it’s finely textured and evenly moist. Fresh pineapple may change consistency.
How should I store pineapple desserts?
Store airtight at room temperature for several days, or freeze baked treats for longer storage.