Pineapple Upside Down Sugar Cookies

I believe dessert should make you feel seen. Like, if a cookie could hug you, it would be this one — slightly dramatic, suspiciously nostalgic, and wearing a tiny pineapple hat. Also: hot takes incoming because someone has to declare that classical pineapple desserts deserve a sugar-cookie glow-up. If you grew up in summers that smelled like sunscreen and regret, you’ll get this. If not, fake it till you bite into one. Try that banana bread chocolate chip cookies twist if you want a related detour (I know you do).

How I spectacularly ruined a tray of Pineapple Upside Down Sugar Cookies

I once made these into glorified fruit marmalades. Not metaphorically — actually. The kitchen smelled like canned pineapple and self-loathing. They were soggy in the middle, loud at the edges (a weird crispy snap), and looked like tiny yellow frisbees. There was a very specific sound when I pulled them from the oven — like a disappointed sigh that also needed coffee. I blamed the oven, then the pineapple, then the concept of joy itself. People at the time were like, “It’s fine.” They lied. I cried. Also, the texture was confusing: chewy where it should be tender, and the sugar sprinkling did nothing but judge me.

I could tell you it was the butter temperature, or the cans, or that one time I forgot to zest my ego, but honestly it was a thousand micro-decisions. (Why do recipes always omit the emotional labor?) Somewhere between “this is salvageable” and “we throw away civilization with this batch,” I learned the difference between a mistake and an identity crisis.

Why this version actually behaves now (mostly)

Because I stopped treating pineapple like a diva and started treating the dough like it was telling me the truth. Small changes: butter at the right softness, pineapple patted almost surgically dry, and rolling the dough smaller so nothing tries to run a coup in the oven. Emotionally I accepted that the cookies might never win a pageant, but they could be lovingly mediocre instead of aggressively tragic.

Also — and this is embarrassingly practical — I started using a tablespoon measure obsession. It’s why these Pineapple Upside Down Sugar Cookies finally cooperate. I still have doubts. Sometimes I think a tiny caramel drizzle would elevate them to nonsense levels of yum, and then I get practical and remember I’m feeding people cookies not launching a dessert startup.

Ingredients

• 1 cup unsalted butter, softened
• 1 cup granulated sugar
• 1 egg
• 1 tsp vanilla extract
• 2½ cups all-purpose flour
• ½ tsp baking soda
• ¼ tsp salt
• 10–12 canned pineapple rings, well-drained and patted dry
• Additional sugar for sprinkling

cheap swaps, texture obsessions, and where you’ll actually find pineapple: budget-wise canned pineapple is the hero here (fresh is cute but slippery). If you like crunch, throw in a little coarse sugar on top — I judge you silently but I get it.

Cooking Unit Converter

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How to get them into the oven without crying

• Preheat oven to 350°F (175°C). Line baking sheets with parchment paper.
• In a large bowl, cream butter and sugar until light and fluffy.
• Beat in the egg and vanilla until well combined.
• In a separate bowl, whisk together flour, baking soda, and salt. Gradually add to the butter mixture to form a soft dough.
• Roll dough into 1½ tbsp balls, flatten slightly, and place on baking sheet.
• Top each dough disk with a pineapple ring, pressing gently.
• Sprinkle sugar on top of pineapple for extra sparkle.
• Bake 12–14 minutes until edges are golden. Cool 5 mins, then transfer to a rack.

Also: don’t overthink the pressing — too hard and you crush the cookie, too soft and the pineapple becomes a jumpy island. If you’re the kind of person who times things to the second, congrats and also calm down. A tip I whisper to myself: tap the pineapple with the back of a spoon so it sorta melds but keeps its pride. Did I mention chilling the dough? Sometimes I do, sometimes I don’t. It depends on my emotional bandwidth.

Are you baking or are we having feelings? (Tell me everything.)

Do you also have a drawer full of baking tools you never use? Who am I asking — of course you do. Do you set out to impress and then make the dough too affectionate and everything flops? Does your oven have opinions? Tell me which appliance is the passive aggressive one in your house. If your kid took one and declared it “sun cookie,” I will cry into mine with you. Also, if you need a gingerbread-esque reassurance for holiday chaos, that link to my classic gingerbread man cookies is a mood: classic gingerbread man cookies. Share your disasters; I will probably offer a therapy cookie.

Common questions you didn’t know you’d ask

I keep thinking about how a cookie can be both an apology and a celebration, and that feels very on-brand right now. Also, I just remembered I left the spoon in the sink, and if I don’t go deal with that it will haunt me, so—

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