Turn cookies on their heads with these pineapple treats

Pineapple upside-down cookies taste just like mini cakes. They are perfect to eat without a fork and would look beautiful on a snack table or for a bake sale.

If anyone tries to tell you that I don’t suffer for my art, please correct them.

After all, I spent a lovely afternoon recently, shoulders deep in my oven with some Easy Off and a scrubber, all thanks to this week’s recipe.

Did my oven probably need a good scrub down anyway? Yeah. Probably.

But it was especially dire when I tried to modify a recipe that called for using a six-well mini cake pan to my normal-sized cupcake tin but didn’t actually change how much batter I put in each well.

Let’s just say that my cups runneth over.

But the cookies were fabulous. They were actually more like mini cakes than cookies in a lot of ways, but I was definitely not complaining.

The recipe I tried comes from the blog “Cookie Dough and Oven Mitt” by Miranda Couse. You can find the original post at https://www.cookiedoughandovenmitt.com/pineapple-upside-down-sugar-cookies. I added extra vanilla in my version and updated the recipe to include using a cupcake tin, for those of us who don’t have fancy mini cake tins.

Pineapple Upside-down Cookies


1 cup butter, room temperature

1 1/2 cups sugar

2 eggs

3 teaspoons vanilla extract

1/2 cup sour cream

3 cups flour

1 teaspoon baking powder

1 teaspoon cornstarch

1/2 teaspoon salt

2, 20-ounce cans sliced pineapples in pineapple juice

6 ounces maraschino cherries

1/2 cup butter, melted

1 cup packed brown sugar


Preheat the oven to 350 degrees. Have a couple six-well mini round cake pans or a couple 12-well cupcake tins at the ready. (There’s no need to grease them.)

In a large mixing bowl, beat the butter and sugar until it is light and fluffy.

Beat in the eggs, vanilla and sour cream, and then beat in the flour, baking powder, cornstarch and salt. Set the mixture aside.

In another bowl, combine the melted butter with the brown sugar, and stir until it is well combined.

If you are using a cake pan, add one tablespoon of the brown sugar mixture to each well. You will likely end up making about 12 to 13 cookies. If you are using a cupcake tin, add about three-fourths of a tablespoon of the brown sugar mixture to the wells until you run out. You may end up making somewhere between 15 and 20 cookies. Spread the brown sugar mixture around to cover the bottom of each well.

Add a pineapple slice to each well. (If you are using a cupcake tin, you’ll want to take a small chunk out of each slice so that it fits flat in the bottom of the well. You can either eat the extra chunks and tell no one or use them to create a ring in one of the wells, too.)

Place a cherry at the center of each pineapple slice.

For the cake pan, use a one-inch cookie scoop to add about three tablespoons of the cookie dough to each well. For the cupcake tin, add around two tablespoons. You only want the mixture to come up about three-fourths of the way in the well.

Bake for 25 minutes or until the edges of the cookies are golden brown.

Let the cookies cool for 10 minutes, and then invert the pan onto waxed paper (be ready for a little bit of a mess, and you may have to rescue some stuck-on pineapples from the pan and place them back on top of the cookies).

Let the cookies cool completely before serving. Store any leftovers in an airtight container.

These really did just taste like mini pineapple upside-down cakes, but they were easy to eat with just your hands, which was awesome.

If you’re nervous at all about your own cookies overflowing a bit, I’d recommend putting the cupcake tin on a rimmed baking sheet, just in case.

Or, you can always take it as a challenge from the universe that your oven needs a good, springtime scrub down. I’m not sure the universe actually cares about such things, but now that the grime is finally out of my stove and out from under my fingernails, that’s what I keep telling myself.

Spice Up Your Life is a weekly recipe column by Lindsey Young, who describes herself as an enthusiastic amateur cook and can be reached through her website at spiceupkitchen.net.

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