PINEAPPLE UPSIDE DOWN COOKIE: A BROWN SUGAR RUM + HONEY GLOW PINAPPLE JAM + SUGARED RED CHERRY COOKIE

Everything you love about a pineapple upside down cake except in a chewy cookie!

Chew chew….a train of thought coming through:

Cake Turned Into Cookie

When looking for my cookie inspiration I love turning to other desserts like ice creams, pastries or cakes! There are a lot of tried and true flavor combinations in these other desserts and its so fun to interpret them in cookie form! Pineapple has been on my mind for some time and I kept gravitating to the ever popular pineapple upside down cake! I love all the flavors in this nostalgic little snack cake: pineapple, rum and cherries. I’ve only had pineapple upside down cake a few times but I’ve always imagined that perfect version would have notes of brown sugar and rum! So even though I’ve never made a pineapple upside down cake, I decided why not embark and make a pineapple upside down cookie!

Let’s talk about the cookie:

• The Brown Sugar Rum Cookie

  • I love adding a little bit of alcohol to my cookies. Just like vanilla, alcohol enhances the dimension of flavors! I usually stick with a good whiskey but since this is a pineapple upside down cake I thought swapping in some rum would be great! While totally optional and very easy to omit, I still highly recommend adding some! The amount is trivial but adds just the right about of je ne sais quoi.

• Brown Sugar Pineapple Jam

  • The star of the show! This cookie couldn’t be called a pineapple upside down cookie without this jam! Sweet honey glow pineapple gets cooked down with dark brown sugar and a touch of vanilla to create the most caramelized golden jam that gets snuggled in that brown butter cookie. This recipe makes a small batch just enough for the cookies but you can easily double it if you want extra for tomorrow’s breakfast bowl or toast!

• Sugared Cherries

  • What is a pineapple upside down cake, eer I mean cookie, without that iconic cherry! Instead of the typical maraschino cherries I wanted to do a more nuanced cherry flavor, one that was more natural rather than sugary sweet. Sweet red cherries, frozen or fresh work, get macerated with sugar to release their excess water and concentrate their flavor. These cherries get studded in the cookie batter for that perfect sweet bite!

PINEAPPLE UPSIDE DOWN COOKIE: A BROWN SUGAR RUM + HONEY GLOW PINAPPLE JAM + SUGARED RED CHERRY COOKIE

Serving: Makes ~17 cookies

Ingredients:

Sugared Cherries

• 1/4 cup pitted fresh or frozen sweet red cherries (30 grams)

• 1 tablespoon white sugar (13 grams)

Small Batch Brown Sugar Honey Glow Pineapple Jam

• ½ cup finely diced pineapple (60 grams)

• 2 tablespoons dark brown sugar (25 grams)

• 1/8 teaspoon salt

• 1 teaspoon vanilla extract

Brown Sugar Rum Cookies

• 2 ¾ cup all purpose flour (330 grams)

• 3/4 teaspoon baking soda

• 1 teaspoon fine sea salt

• 1 cup of unsalted butter, at room temperature (226 grams, ~2 sticks)

• 1 1/4 cup of dark brown sugar (250 grams)

• ½ cup white sugar (100 grams)

• ½ teaspoon molasses

• 1 tablespoon vanilla extract

• 1 teaspoon rum

• 1 egg

• 1 egg yolk

• Raw sugar, to sprinkle

Method:

Making the Sugared Cherries

1. Give the cherries a rough chop.

   • 1/4 cup pitted fresh or frozen sweet red cherries (30 grams)

2. Sprinkle the cherries with white sugar and set aside for about 20 minutes.

   • 1 tablespoon white sugar (13 grams)

     • Alternatively, you can also do this the night before. Place the cherries and sugar in an airtight container in the fridge overnight.

3. Once the cherries have been macerated in the sugar, press the cherry mixture through a strainer, separating the extra liquid from the cherry mixture. Set the drained cherry mixture to the side.

   • Note: Don’t throw out that cherry syrup! Add it to your iced matcha or add it with some iced sparkling water for a refreshing drink!

Making the Small Batch Brown Sugar Honey Glow Pineapple Jam

1. Add the pineapple, dark brown sugar, salt and vanilla extract into a medium sized pot and heat over medium heat.

   • ½ cup finely diced pineapple (60 grams)

   • 2 tablespoons dark brown sugar (25 grams)

   • 1/8 teaspoon salt

   • 1 teaspoon vanilla extract

2. Cook the mixture for about 8-10 minutes until the mixture is thick and you can drag a spatula or spoon through the jam and leave a line.

3. Smash the pineapple jam a few times with a spoon or pulse the mixture with a immersion blender to help smooth the jam.

4. Let the pineapple jam cool. Once cool, store in an airtight container and set aside.

Making the Brown Sugar Rum Cookies

1. Preheat your oven to 350 degrees. Line two half sheet baking pans with parchment and set aside.

2. Combine the all purpose flour, baking soda, salt and whisk until incorporated. Set aside.

   • 2 ¾ cup of all purpose flour (330 grams)

   • 3/4 teaspoon baking soda

   • 3/4 teaspoon fine sea salt

3. In a stand mixer or with an electric mixer, beat butter on medium speed for a few minutes just until fluffy and pale.

   • 1 cup of unsalted butter, at room temperature (226 grams, ~2 sticks)

4. Add the dark brown sugar and light brown sugar to the butter and beat for another 2 to 3 minutes until light in color and creamy.

   • 1 1/4 cup of dark brown sugar (2350 grams)

   • ½ cup white sugar (100 grams)

     • Note: Scrape the sides of your bowl in between to ensure that everything is combined.

5. Add molasses, vanilla extract, rum if using, the egg and the egg yolk into the creamed butter/sugar mixture and beat for 2 to 3 minutes or until the mixture is well combined.

   • ½ teaspoon molasses

   • 1 tablespoon vanilla extract

   • 1 teaspoon rum

   • 1 egg

   • 1 egg yolk

     • Note: Make sure to scrape the sides and bottom of the bowl to get any dry bits that haven’t been incorporated.

6. In batches, add the flour mixture to the wet mixture and blend on low speed until barely combined.

   • Note: Make sure to scrape the sides and bottom of the bowl to get any dry bits that haven’t been incorporated.

7. Add in the chopped pineapple jam into the cookie dough batter and mix until it is evenly distributed.

   • Small Batch Brown Sugar Honey Glow Pineapple Jam

8. Add in the chopped cherries into the cookie dough batter and mix until they are evenly distributed.

   • Sugared Cherries from above

9. Use a large 3 tablespoons sized cookie scoop to scoop out all of the dough. You should have about 16-17 cookie dough balls.

   • For super uniform cookies, you can weigh the cookie dough to make sure each one is about 60 grams each.

10. Line a baking pan with parchment paper. Place 5 cookie dough balls on the tray, leaving 2 inches of space between each ball.

11. Place 5 dough balls onto each baking sheet pan and let them bake for about 8-10 minutes or just until the sides of the cookies are set and the center gently puffs.

12. Pull the cookies out and scoot the cookies into position using a round ring to make the cookies thicker and circular. (These cookies will spread quite a bit so its best to scoot them into shape to make them thicker and round)

13. Once the cookies have baked, let them cool on the tray for about 5-10 minutes until cool to handle. Move the cookies onto a wire rack to fully cool.

14. Top the cookies with raw sugar for a bit of crunch! Enjoy warm or at room temperature.

Storing + Making & Freezing Ahead of Time

Storing Once Baked

1. Once baked, the cookies will stay fresh in an airtight container outside for up to 2 days.

Making & Freezing Ahead of Time

1. If you’d like to make the cookie dough ahead of time you can do that too!

   • If you plan on baking the cookie dough within a day or two of making the dough you can place the scooped cookie dough in a tray/plate and wrap it tightly with plastic wrap in your fridge until ready to bake. When ready to bake, let the cookie dough come to room temperature for about 30 minutes to an hour until no longer cold. Bake as directed.

   • If you’d like to freeze your cookie dough to bake later on (up to a month later) place the scooped cookie dough on a parchment lined plate/tray and give the dough a little room in between each other. Let the cookie dough freeze on the tray/plate for at least 2 hours, then you can pull the cookie dough off the tray and place the frozen cookie dough into an airtight freezer safe storage bag/ container. When you are ready to bake, take out as many cookies as you’d like and let them com toe room temperature outside, about 1-2 hours. Once thawed, bake as directed.