Pineapple Upside Down Cake

If you follow me on Instagram, you may notice that I’m participating in Project Life 365.  I’m not just taking a photo every day (& instagramming it), but Project Life has created a specific word or phrase that the photo for that day should embody.  I’ve tried (and failed) several previous 365 projects, but so far, I have been successful with this one (fingers crossed).

Each photo I take for Project Life 365 is hashtagged with #projectlife365 and with a hashtag for that day’s word or phrase. Some days the theme is more challenging. Some days, I know instantly what image I would like to take.

Regardless, it’s fun to be a part of a community of photographers, both amateur and professional, all taking part in a common daily challenge.  I love scrolling through each day’s images & seeing how others have been inspired by that particular day’s theme.

Last week, one of the challenges was #upside_down.  Being the food-oriented person that I am, I immediately thought of an upside down cake.  And, it just so happened that I had an almost too ripe pineapple begging to be used. Voila! Project Life 365 inspired me to make this cake.

Several times in the past I have made pineapple upside down cake--my first ones probably with boxed cake mix.  But my later versions have all used the pineapple upside down cake recipe from Thomas Keller’s Ad Hoc at Home.

When I discover a recipe that really works, it’s sometimes hard to try a new one for fear that it may not turn out as well as the previous version. I love that his recipe calls specifically for Vanilla Bean Paste--one of my favorite ingredients--and fresh pineapple--sometimes the canned pineapple is a little too mushy for me.

While Keller’s recipe suggests using a silicone pan, I did go out on a limb this time & I used my beloved cast iron skillet as the baking pan instead of the silicone.  We now use the cast iron on nearly a daily basis, and it practically lives on one of the back eyes of the stovetop!  My pan is well seasoned at this point, but I still gave it a brushing with some melted butter, just to add some extra insurance.  It worked perfectly!

There’s always something both wonderful and terrifying about building a dessert upside down.  The fruit has to be rearranged backwards, because what is the top when you’re assembling it will become the bottom once it is baked.

And I always feel a bit of hesitation before unmolding the dessert, because there is that element of surprise or unknown.  But I do love the feeling of satisfaction when the dessert is unmolded & the beautiful, slightly caramelized pineapple designs are visible.  I think it’s the perfect way to portray #upside_down.

RECIPE
Adapted from Ad Hoc at Home

note: the pan schmear makes more than what is needed for a single cake, but it is difficult to scale it down. I have tried just using all of the smear, but sometimes, I have found too much schmear makes the cake a little soggy. Store any leftovers in the fridge for a future use.  Or heat them to a boil (to dissolve the sugar) and use it as an extra sauce to pour over the already baked cake before serving. Also, if you can’t find Vanilla Bean Paste, feel free to substitute Vanilla Extract.  But as I mentioned before, VB Paste is one of my favorite ingredients, so even if you have to order it online, I highly suggest getting some!   

Pan Schmear 
1 stick/4 oz Unsalted Butter, room temperature
1 1/2 Tbl Honey
1/2 tsp Rum (I substituted Bourbon because I did not have any rum)
1 c Brown Sugar, packed
1/4 tsp Vanilla Bean Paste

1.  In the bowl of a stand mixer fitted with the paddle attachment, cream together all the ingredients.  Mix until smooth & slightly fluffy.  
2. Spread 1/3 to 1/2 cup of the mixture into the bottom of a 9" silicone pan (or in my case, a lightly greased cast iron skillet).  Set aside.  

Cake & Assembly
1 pineapple
1 1/2 c Cake Flour (I used Jeanne's Gluten Free AP Flour Mix)
2 tsp Baking Powder
1 stick/4 oz Unsalted Butter, room temperature
1/2 c plus 2 Tbl Granulated Sugar
1/2 tsp Vanilla Bean Paste
2 eggs, room temperature
1 Tbl + 1 tsp Milk, room temperature

1. Preheat the oven to 350 F. 
2. Prepare the pineapple.  Start by placing the pineapple on it’s side and cutting off the top and the bottom. Stand the pineapple up on a cutting board, so that it is resting on the bottom cut surface. Use a very sharp chef knife to slice off the skin of the pineapple, following the contours of the pineapple trying to cut only as much as necessary off.  Work your way around the pineapple until all the skin has been removed.  Once all the skin has been removed, turn the pineapple back onto its side & slice it into pieces approximately 1/8-inch to 1/4 inch in thickness.  Use a small circle cutter to cut out the core.  Leave in rings or cut into quarters.  Artfully arrange the pineapple over the schmear in the bottom of the pan.  Remember that the bottom will become the top!  You may not need all the pineapple.  
3. In a small bowl, whisk together the flour & baking Powder.  Sift if the flour is lumpy.  Set aside.
4. In the bowl of an electric mixer fitted with the paddle attachment, cream the softened butter & granulated sugar.  Mix on medium speed until the mixture is very fluffy, has lightened in color, and has increased in volume (approximately 3 minutes). Add the Vanilla Bean Paste. Scrape down the sides of the bowl. 
5. Add the eggs, one at a time, mixing on low speed. Scrape down the bowl between additions.  
6. Mix in the milk. Add the flour in two batches, scraping down the sides of the bowl after each addition.  Mix just until combined.  
7. Spread the cake batter evenly over the arranged pineapple slices.  
8. Bake the cake for 15 minutes, then rotate the pan & bake for another 20 to 25 minutes, or until a cake tester (or toothpick) inserted into the center of the cake comes out clean. 
9. Allow the cake to cool at room temperature for 20 to 30 minutes, but not any longer or else the cake may be difficult to get out of the skillet. 
10. Run a knife, gently, around the side of the skillet to loosen the cake.  Place the intended serving plate or pedestal over the top of the skillet & flip.  Allow gravity to help loosen the cake.  If some of the pineapple remains in the pan, scoop it out & place it on it’s original location on the cake. No one ever has to know :)
11. Serve warm.  Cover any leftovers & store at room temperature for up to 2 days.