Preview II: Ad Hoc Pineapple Upside-Down Cake Recipe

My first attempt at pineapple upside-down cake.

I’ll let you in on a secret: I’ve never made this iconic Americana dessert before.

Sure, I’ve made my share of pineapple compote for glistening slabs of baked ham. I’ve chopped mounds of pineapple for salsa for grilled fish tacos. And of course, I’ve enjoyed plenty of fresh pineapple au naturele.

But pineapple upside-down cake kind of frightened me, I must admit. Maybe it’s because so many recipes call for baking it in a cast-iron skillet that you then have to flip over to invert onto a serving plate. Yeah, flipping over a scorching hot skillet containing molten caramelized syrup (and we all know how cast-iron retains its heat) just seemed like a recipe for not just cake, but third-degree burns to boot.

Then along came the promotional brochure in the mail for the upcoming “Ad Hoc At Home” cookbook (Artisan) by Thomas Keller with his rendition of this homespun cake.

The book won’t be out until November. But after trying the fantastic recipe for Ad Hoc’s “Chocolate Chip Cookies” last week, I decided to put my fears aside to attempt Ad Hoc’s “Pineapple Upside-Down Cake.”

A silicone cake pan makes it a breeze.

No cast-iron skillet needed here.

Instead, Keller uses a 9-inch silicone cake pan.

He doesn’t melt and caramelize the sugar and butter in the pan beforehand, either, like many other upside-down cake recipes. Instead, he creates a “schmear” of softened butter, light brown sugar, honey, dark rum, and vanilla that gets spread all over the bottom of the pan.

Then, a light sprinkle of salt goes over the top. Next, quartered rings of fresh pineapple are overlapped in the pan before the cake batter is added.

After baking, the cake rests in the pan for a short while. Then, you invert it onto your serving platter — with no fuss, no bother, and no dialing 911.

Because the silicone is so flexible, the cake releases easily with no sticking whatsoever.

Take a bite. Juicy, tender, sticky pineapple gives way to melty brown-sugar syrup then to an incredibly buttery, tender crumb. The touch of salt is a welcome addition, ensuring this cake isn’t candy-sweet like those in grandma’s time.

Pretty in pineapple.

It’s a fairly easy cake to make, but one that looks quite dramatic when unveiled. Best yet, because fresh pineapples are available year-round, you can serve this cake any time of year.

You can bet that I’ll be making this again.

Pineapple upside-down cake rookie?

Not any more.

Pineapple Upside-Down Cake

( serves 8 )

Thomas Keller writes: Here is another slightly zany entry from the American tradition, pineapple upside-down cake. I have some affection for canned pineapple for nostalgic reasons, but we use fresh pineapple here for a more elegant dessert. Again, think of this as a general template that you can use for different fruit — apple, blueberries, and the like all work wonderfully. We make what we call a “pan schmear” of butter and brown sugar, top it with the fruit, and pour the cake batter over the top. The recipe makes more schmear than you need, but it is difficult to make less. It will keep for a couple of weeks in the refrigerator, ready when you want to make another cake, or it can be frozen.

For pan schmear:

8 tablespoons (1 stick) unsalted butter, at room temperature

1 1/2 tablespoons honey

1/2 teaspoon dark rum

1 cup packed light brown sugar

1/4 teaspoon vanilla paste or pure vanilla extract

Kosher salt

1 Gold (extra -sweet) pineapple

For cake:

1 1/3 cups cake flour

2 teaspoons baking powder

8 tablespoons (1 stick) unsalted butter, at room temperature

1/2 cup plus 2 tablespoons granulated sugar

1/2 teaspoon vanilla paste or pure vanilla extract

2 large eggs

1 tablespoon plus 1 teaspoon milk

Preheat oven to 350 degrees.

In the bowl of  a stand mixer with the paddle, combine the butter, honey, rum, sugar, and vanilla, and beat until smooth and well blended. Spread 1/3 cup of the schmear over the bottom of a 9-inch silicone cake pan. Sprinkle lightly with salt. (The remaining schmear can be refrigerated for up to 2 weeks or frozen for up to 1 month; bring to room temperature before using.)

Cut top and bottom from pineapple, and cut away peel. Cut pineapple lengthwise into quarters, and cut off core from each section. Cut each piece crosswise into 1/8-inch-thick slices. Beginning at the perimeter of the pan, make an overlapping ring of pineapple slices with the curved side facing out. Make a second ring inside the first one, overlapping the slices in the opposite direction, working toward the center of the pan. Reserve any pineapple for another use.

Sift flour and baking powder together; set aside.

Put butter and sugar in the bowl of a stand mixer fitted with the paddle and mix on low speed to combine, then beat on medium speed for about 3 minutes, until light and creamy, stopping to scrape down the sides as necessary. Mix in vanilla. Add eggs one at a time, beating until the first one is incorporated before adding second and scraping down the sides as necessary. Beat in milk. Add flour mixture in 3 batches, beating just until combined.

Pour batter into pan and spread over pineapple. Bake for 15 minutes. Rotate the pan for even browning and bake for another 20 to 25 minutes, until a cake tester or wooden skewer inserted in the center of the cake comes out clean. Cool cake in the pan on a cooling rack for 20 to 30 minutes.

Run a knife around the edges of the cake, invert onto a serving platter, and serve warm. (Leftover cake can be stored at room temperature for up to 2 days.)

From “Ad Hoc At Home”

Ad Hoc’s Chocolate Chip Cookies Recipe

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  • MMM, that looks wonderful. Now I need to get a silicone cake pan.

  • I admit that I have never eaten Pineapple Upside Down Cake. This looks delicious though! I will have to try this recipe. Love the fact that it isn’t too complicated either.

  • That’s a dessert I particularly love! It reminds me of my English grandmother… Your Upside-Down Cake looks very tempting!

    I eat mine warm with a drizzle of unsweetened condensed milk.



  • Once again, I know what I’ll be making this weekend!

  • Oh yum. That looks so good! Think it would work with a regular cake pan, or did you have to really give it a good twist to get it to drop out?

  • How delicious! I love making upside down cakes (yes, with the molten caramel and skillet), but this looks like an interesting method and it came out beautifully!

  • Of all the meals I’ve had at Ad Hoc (25+), I’ve never had the pineapple upside down cake. This looks delicious and I hope you have more recipes to preview for us. πŸ™‚

  • Easy? The key ingredient (pan schmear) calls for mixing with paddle of a STAND MIXER. Hoo hah — being fresh out, I’m rushing to Target for one. Maybe, two if they have ’em in Avocado and White.

  • I looove pineapple upside down cake! My mom would always make it from the box, and would dump the butter and brown sugar in the cake pan and put it on the stove. That melted butter/sugar baked into the cake is the best part. this recipe looks especially delicious!

  • Arnold: You are my hero for getting to eat at Ad Hoc 25-plus times! And yes, I have two more Ad Hoc preview recipes to share in the next week or so. After that, we all just have to wait until the actual cookbook comes out in the fall.

    Suzy: I think you could use a regular cake pan, though it might be a little bit more work to get it out of the pan. But I have definitely seen some other pineapple upside-down cake recipes that are baked in regular cake pans, so it’s definitely do-able.

  • I have all of the other Thomas Keller cookbooks. I can’t wait to get my hands on this one!

  • so simple and looks so yum!

  • I made this once, but with cornmeal! yours look absolutely perfect, even though it’s you first time! Do you have any leftovers? hee hee!

  • Oh, how I love pineapple upside-down cake. My mom used to make it for my brother, sister and I all the time while growing up. Your cake came out so lovely. Mmm…now I’m craving a slice!

  • Very nice recipe and nice colorful Photo. Il like to taste some slice, yummy. πŸ™‚

  • I actually made a pineapple upside down cake yesterday – coincidence! So delicious. It did get me wondering if anyone’s ever made a pineapple right-side-up cake…

  • I’ve never made a pineapple upside down cake but I used to make one with apples and always baked it in a round cake pan. I haven’t really heard of doing it in a skillet.

  • I was sure I needed the book when I saw the cookies, and now I can’t wait for it to get on the shelves! This looks great, and the fresh pineapple sounds delicious.

  • This has always been one of those favorites made by grandmas and aunties. Always good with ice cream. Who knows if they put rum in it, but we personally think the rum is necessary!

  • Wow, another dessert thats going to get me in trouble but what a way to go, the recipe sounds fantastic!

  • Gosh, I think I’m on the same wavelength as you, Carolyn. I just made my first upside down cake for a 4th of July BBQ a few days ago. Now, reading your post, I couldn’t agree with you more. Not too hard to make, but such an impressive result. Yours looks delicious! High five!

  • I’ve never made pineapple upside-down cake either; this looks like a great recipe to start. I’ve hesitated to buy silicone pans, worried how they might affect browning and texture of baked goods but they seem so easy to use. Hmmm . . . can I use this recipe as an excuse to buy the pan? “But Thomas Keller uses it . . . !”

  • I didn’t have a silicone cake pan and was trying to get away with using a spingform pan. It leaked and lost some liquid, I had to put a baking sheet under it to stop the mess but the cake turned out great still, not very sweet, very fruity and buttery. Now that I know I will be making this again and again I went and got the proper tool and it worked awesome.

  • Charlie’s Mom: Glad you got a silicone pan. It definitely makes baking this cake a breeze. I, too, like how this dessert isn’t sugary sweet. Made it again for a dinner party last week, and it was an all-around hit.

  • I made it using a metal pan, and had no issues, though a silicone pan is on my wish-list.

    After a success with the recipe as written, being adventurous, I tried it with cantaloupe instead of pineapple. Must say, it worked out great. moist and mellon-y. I’m thinking blackberries may be next….

  • Tried this recipe out today. I doubled the cake batter recipe and made two (metal) 9-inch cake rounds. I wish I would have looked more carefully at the picture and gone with more pineapple than I did (and arranged it in a prettier fashion), but overall it turned out very well. I put the leftover smear in a saucepan and let it simmer for about 3 mins until it was caramelizing. I went ahead and topped the two cakes with this since I really didn’t want to save the little that was left for another day. The cake tastes light and fluffy with a browned, thin crust. Delicious!

  • My pineapple upside down cake is not coming out of the skillet. What might help keep it from turning into pineapple pudding (might have to dish it up into a bowl!)?

  • Barbara: It’s really best to use a silicone cake pan for this dessert, as it makes unmolding a breeze. However, what kind of skillet are you using? Is it a seasoned, cast iron pan? If so, it should slide out easily then. Otherwise, yes, you might have to use a knife and spatula to slip around the edge of the pan to loosen the cake. If you only get the cake part out, you can try to scoop out the pineapple top and artfully arrange it back on top. Hope that helps!

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  • Now THAT is an impressive classic upside down cake.

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  • Pingback: Pineapple Upside-Down Cake – Sali Sweet

  • — You have reprinted my entire original post and photos without my permission. Please remove it from your site. Do your own content. Stop plagiarizing.

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