Pineapple-Almond Upside Down... Cookies!




About: ♫ Basking in sunshine ☼, creating new dishes... growing zucchini and swimming with fishes. Rattlesnake hunting the desert in Spring; these are are a few of my favorites things. When the wind flies, when the...

The moist, delicious yumminess of classic Pineapple Upside Down Cake has been captured ...  in a Cookie!

They're like a little taste of Springtime to brighten the Winter blues.

Happy New Year... Enjoy!

Step 1: Ingredients, Tools and Prep Work

This recipe makes approximately 2 dozen cookies.


2 1/2 cups Flour
2 teaspoons Baking Powder
1/4 teaspoon Salt

1/2 Cup Butter-softened
3/4 cup White Sugar
2 Eggs
1/3 cup Sour Cream
2 Tablespoons reserved Pineapple Juice
1 teaspoon Vanilla extract

Sliced Almonds
Maraschino Cherries
1 - 28 oz can of Pineapple rings- drained- juice reserved. 

1/4 C Brown Sugar- packed
1 teaspoon Light Corn Syrup

Electric Mixer
Nonstick Baking mat (Silpat) or parchment paper
Mixing Bowls

Prep work:

Remove the pineapple rings from the can. Place them on a paper towel and gently pat dry. (Save the canned juice.) Cut each ring into small wedges as pictured. Place in a bowl. Add brown sugar and Corn syrup. Toss to coat.

Drain maraschino cherries on a paper towel. Cut in half.  Place the cherries on the baking sheet, domed side-down. Space them about 4-5 inches apart.  Lay the almond slices in a circular, flower-fashion around the cherry. Follow suit with the pineapple wedges, using 5 per cookie.

These cookies do not spread very much but give yourself plenty of room on the first batch so you can better gauge the spacing.

Motorhome living requires me to bake in a Toaster Oven. I started with 4 cookies on a sheet and found I could fit 6 if I was careful.

Next Step---> Batter preparation--->

Step 2: Mix and Bake

Preheat Oven to 325 degrees

Whisk the flour, baking powder and salt together in a medium bowl.  Set aside.

In a larger, deeper bowl,  use a hand mixer (medium-high speed) to cream the butter first. Add the white sugar and whip until smooth.

One ingredient at a time, add eggs, sour cream and vanilla. Mix the batter  thoroughly as you add each ingredient and remember to scrape the sides of the bowl, too.

1/2 cup at a time, slowly add the dry ingredients to the batter, mixing on low speed. Scrape the bowl after each addition. Mix well. 

Spoon the batter into a pastry bag or ziplock baggie.  Snip off about 1/3" from the corner.

Begin at the cherry center and slowly pipe the batter outward  in a spiral. Leave about 1/4" of pineapple wedges uncovered to allow for spreading.

Bake for 20- 23 minutes or until golden brown. Note: If you undercook, they will not hold their shape very well.

Allow the cookies to cool for 10 minutes. Use a spatula to gently invert them upside down onto your cookie plate.

Serve at room temperature.

Step 3: Serving Suggestions:

On day 1, these cookies will hold their shape beautifully.

On day 2 they are softer and more difficult to hold in your fingers.

The delicious solution?

Plate your cookies, top with a generous dollop of whipped cream and eat them with a fork!

Cookies Challenge

Finalist in the
Cookies Challenge



    • Pie Contest

      Pie Contest
    • Fat Challenge

      Fat Challenge
    • Jewelry Challenge

      Jewelry Challenge

    19 Discussions

    Thank you for such a nice comment!

    btw,,, your website is FUN, refreshing and utterly DELIGHTFUL!

    I'm an exPat living in Baja California. The weather here is currently WARM! ;-)


    7 years ago on Introduction

    I have some pineapple every morning and would still have room for that great cookie.

    3 replies

    Reply 7 years ago on Introduction

    I adore pineapple, too.

    It's my favorite fruit... when combined with vodka! ;-D


    7 years ago on Introduction

    These cookies are so beautiful! I also like the idea of swirling the batter on. In the pictures the texture looks similar to angel food cake. Is it? Or Is it more like a shortbread cookie? Just curious I'm kind of a texture person. :)

    1 reply

    Reply 7 years ago on Introduction

    Not shortbready... and It's definitely "cakey" just not in an angel food way.

    I think the texture contributes to the pretty presentation, too.

    Thanks for noticing and for your nice comment!