Pineapple Cookies & Pineapple Squares (2 Vintage Recipes)
Two easy vintage pineapple recipes using canned crushed pineapple: soft, chewy Pineapple Cookies and classic Pineapple Squares with a buttery oatmeal crumble topping.
Use the jump links below to go straight to the recipe you want.
Recipes on this page
Pineapple Cookies
Ingredients
- 1 cup brown sugar
- 1 cup white sugar
- 1 cup shortening
- 2 eggs
- 1 can (8 oz or 20 oz) crushed pineapple (with juice)
- 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 the crushed pineapple (do not drain).
- Cream shortening with brown sugar and white sugar. Beat in eggs.
- Add pineapple mixture and mix until well blended.
- In a separate bowl, whisk together flour, salt, baking soda, and baking powder.
- Gradually stir dry ingredients into the batter until just combined.
- Drop by rounded spoonfuls onto the cookie sheet.
- Bake 12–15 minutes, until edges are lightly golden. Cool on the sheet for 2 minutes, then transfer to a rack.
Total bake time: 12–15 minutes
Equipment: cookie sheet
Yield: about 3 dozen cookies
Pineapple Squares
Ingredients
- 1 can crushed pineapple (with juice)
- 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 (quick or old-fashioned)
- 1 cup Crisco (or shortening)
- Confectioners’ sugar (for dusting)
Instructions
- Preheat oven to 350°F. Grease a 7½ × 7½-inch square pan (or 8×8-inch).
- In a saucepan, combine crushed pineapple, sugar, cornstarch, and lemon juice. Cook over medium heat, stirring constantly, until thickened and clear. Set aside to cool slightly.
- In a large bowl, mix flour, salt, brown sugar, oatmeal, and Crisco until the mixture is crumbly.
- Press half of the crumb mixture firmly into the bottom of the prepared pan.
- Spread the pineapple filling evenly over the base.
- Sprinkle the remaining crumb mixture on top and press down lightly.
- Bake 30–35 minutes, until golden brown.
- Cool completely in the pan, dust with confectioners’ sugar, and cut into squares.
Variation: Substitute cherry pie filling for the pineapple filling. Serve warm with vanilla ice cream.
Total bake time: 30–35 minutes
Equipment: 7½ × 7½-inch (or 8×8-inch) pan
Yield: 16 squares
Pineapple Cookies & Squares FAQ
Do I need to drain crushed pineapple?
No. Use the crushed pineapple with its juice. The liquid adds moisture and flavor to both recipes.
How do I know when pineapple cookies are done?
They’re done when the edges are lightly golden and the centers no longer look wet or glossy.
Can I substitute fresh pineapple?
Canned crushed pineapple works best for consistent texture and moisture. Fresh pineapple may require draining and chopping finely, which can change the result.
How should I store pineapple desserts?
Store airtight at room temperature for up to 4 days, or freeze baked cookies and squares for up to 3 months.