I had very little faith in this cookie idea -- I mean, a pineapple upside-down cake in cookie form.
I was thinking -- too much moisture, raw dough, wet cookie.
I looked around on the Internet.
I found recipes calling themselves pineapple upside-down cookies, but they were mostly fruit cookies with icing or cookies topped with pineapple/caramel after-the-fact.
No -- I wanted (actually we wanted -- this was one of my husband's ideas again) caramelized pineapple, brown sugar, the whole yummy bit.
So this is what I came up with...
They're freaking fabulous, I tell you.
Addictive. All the flavors of the cake in a tiny two-bite cookie.
And that cookie -- it's just crisp enough to hold the topping -- NOT hard or crunchy.
The cookie base and topping hold together so well, too.
The cookie is sweet and crisp around the edges with that retro, slightly gooey caramelized pineapple topping.
And it's simple enough to make.
I just popped the pineapple, brown sugar and butter in mini-muffin cups, then topped them with cookie dough...
I turned the tiny cookies out of the pan just like pineapple upside-down cake...
Except these are all cookie, baby.
And there's no stopping at just one piece.
Pineapple Upside-Down Cookies
- 3/4 cup sliced pineapple, well-drained (I cut up about 4-5 rings really well)
- 1/4 cup (1/2 stick) unsalted butter, melted
- 1/2 cup light brown sugar
for the cookie dough:
- 1 1/3 cup flour
- 1 teaspoon cream of tartar
- 1/2 teaspoon baking soda
- 1/8 teaspoon kosher salt
- 2 tablespoons granulated sugar, plus 1/4 cup more for rolling
- 1/2 cup light brown sugar
- 1/2 cup (1 stick) unsalted butter, at room temp.
- 1 large egg, at room temp.
- 3/4 teaspoon pure vanilla extract
- 1/8 teaspoon almond extract
- fine sea salt, for sprinkling
Preheat oven to 350 degrees. Grease or spray a 24-cup mini-muffin pan with canola spray very well.
For the pineapple topping: Pour 1/2 teaspoon of the melted butter in each mini-muffin cup. Place 1 teaspoon of light brown sugar in each cup. Place 1 heaping teaspoon of well-cut up pineapple on top of the brown sugar. Press the pineapple into the brown sugar. Set aside.
For the cookie dough: Pour the 1/4 cup granulated sugar in a bowl and set aside.
In small bowl, whisk together the flour, cream of tartar, baking soda and kosher salt.
In large bowl, beat the butter, 2 tablespoons granulated sugar and brown sugar on medium-high speed until creamy, about 2 to 3 minutes. Add egg and beat until well-combined, about 1 minute. Add extracts and beat to combine. Stir in flour mixture until combined.
Take a heaping 1/2 tablespoon of cookie dough, roll into a ball and then roll dough ball in the granulated sugar.
Place 1 cookie dough ball on top of the pineapple in each mini-muffin cup. (See note on how to use that bit of leftover dough.)
Bake for about 20 to 24 minutes, until tops of cookies are a rich golden brown and any visible juices around the edges are bubbling. Do not underbake!
Cool cookies in pan on wire rack for about 5 minutes.
Carefully run a butter knife or plastic knife around edges of the cookies. Invert pan on wire rack, so that the caramelized pineapple bottoms become the tops of the cookies.
Scoop out any pineapple-brown sugar mixture that remained in the pan and place on cookies.
Sprinkle just a tiny bit of fine sea salt on the pineapple tops of each cookie.
Allow to cool (if you can stand to wait), then enjoy!
Note: You'll have enough leftover dough for a few snickerdoodles. Just be sure to bake this batch of snickerdoodles for less time than the original recipe, only about 10 - 12 minutes, until tops are cracked.