Pineapple Upside Down Cake Recipe with Fresh Milled Flour
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This pineapple upside down cake recipe is the only one you’ll ever need from here on out! It is crazy good, super easy, and made with FRESH MILLED FLOUR!!!!!! I took this recipe from King Arthur Flour and converted it to suit me better.
Because I’m better than you.
If you don’t follow me on social media, that last sentence may have offended you. I also don’t care, but it’s a joke with everyone on there. We all gotta get upset when someone says fresh milled flour is better than dead flour and feel attacked. GOOD. You should feel attacked, because fresh milled flour IS better. And it absolutely makes this pineapple upside down cake recipe.
I’m done picking.
This pineapple upside down cake recipe uses fresh milled soft white wheat that is not sifted. I know the popular thing to do with cakes is to sift them, but I despise sifting anything. It is pure torture. So I am to figure out what I’m doing with the least amount of fancy steps. Sometimes we overcomplicate things to the point of not wanting to do it anymore and I’m not about that.
I also like to use my mock zucchini pineapple I can for this pineapple upside down cake recipe. You can use store bought, fresh, or zucchini… I don’t care! But if you’d like to learn how to can your own mock zucchini pineapple, check that out here. Zucchini grows in Ohio a whole lot easier than pineapples do :D
I also use my home canned maraschino cherries, which you can learn how to make and can here. I despise store bought maraschino cherries… they are GROSS. But I really enjoy homemade, sans the poison. They do turn a little dark to brown after baking, but we don’t get all bent out of shape about it. It tastes really good.
I most recently made this cake for my son’s birthday. It is his favorite kind of cake, and as his mother who always wanted a pineapple upside down cake, too, I happily oblige. I went all out for him and made two cakes and we enjoyed a double decker. Just plopped one out of the pan right on top of the other. Super fancy and so, so so decadent.
Tips for Making a Cake with Fresh Milled Flour
Rest the batter. A minimum of 20-30 minutes is helpful, but if you can, omit the leavener and soak everything for several hours, or even overnight covered with an airtight lid. This allows the fresh milled flour to rehydrate (it doesn’t rehydrate instantly like dead flour) and also softens the germ so the flour doesn’t get all crusty and make for a dense cake.
Use a fermented dairy for the milk portion. I like to use kefir and that added to the fresh milled flour really helps ferment and break down the grains to make them ultra digestible, but also much more fluffy after baking.
Once the cake is nearly cooled, cover it tightly with plastic wrap or put it in an air tight container. This helps not allow the cake to dry out, like it really badly wants to (thanks fresh milled flour), and traps that warm steam leaving your cake to give you a soft and moist cake. Trust me!
Now, let’s make the best pineapple upside down cake recipe!
Equipment You Might Want
- 9-inch round cake pan
- Cooling rack
- Stand Mixer
- Grain Mill
- Mixing bowl with a lid
Ingredients
Topping
- 4 Tbs butter
- 1/2 cup sugar
- 1 Tbs molasses
- 1/4 tsp cinnamon
- 1/4 tsp ginger
- 1 pint mock zucchini pineapple, drained
- 1 pint maraschino cherries, drained
Cake
- 3 Tbs butter, room temp
- 3/4 cup sugar
- 4 quail eggs, or 1 chicken egg
- 1/2 tsp salt
- 2 tsp vanilla extract
- 1 1/2 cup fresh milled soft white wheat, chilled
- 2 Tbs cornstarch
- 1/2 cup milk kefir
- 1 3/4 tsp baking powder
Step 1: Make the Sponge
To the bowl of your stand mixer, add the butter, sugar, and molasses. Beat until smooth, this takes a few minutes. Stop to scrape the bottom of the bowl once or twice.
Mix in the eggs, salt, and vanilla extract.
Mix the fresh milled soft white wheat and cornstarch together. Add about 1/3 of the flour, followed by 1/2 of the kefir, alternating once more and ending with a final addition of the flour mixture. Mix only until smooth. Scrape the bottom of the bowl and sides down and hand mix if needed.
Transfer batter to a bowl with a tight fitting lid and allow to sit and rest a minimum of 30 minutes, but preferably about 12 hours.
Step 2: Baking
Start by grease the 9-inch round cake pan with ghee.
Preheat oven to 375 degrees F.
Make the topping: In a sauce pan, melt the butter, sugar, molasses, cinnamon, and ginger. Pour into the prepared cake pan.
Evenly scatter the mock pineapple zucchini and maraschino cherries on the bottom of the pan. You can also use pineapple chunks or rings in place of the mock pineapple zucchini to be extra pretty like I did in the recipe photo.
After resting, stir in the baking powder, mixing to incorporate and being careful not to overmix. The batter will be very thick. Spoon the batter overtop of the caramel and pineapple. Press to spread out as well as you can but it’s okay if it doesn’t go completely to the edges.
Bake the cake for 30 minutes, or til a toothpick inserted into the center comes out clean. Ovens vary!
Step 3: Assemble
Once cake is done, remove from oven to a cooling rack. Run a knife around the edge of the pan carefully and allow the cake to cool for 3-5 minutes.
Turn the pan over onto a serving plate and gently tap the bottom of the cake pan. Wait about 30 seconds and lift the pan off. If it sticks lift the pieces out of the pan and place it back on the cake… it’ll taste just fine. Promise.
Let cool, and serve warm or at room temperature. Once cooled, wrap tightly or place in an air tight container to prevent the cake from drying out. Fresh milled flour baking likes to dry out much faster than dead flour!
Notes:
I don’t make nor buy brown sugar, so I just add unrefined cane sugar and molasses to recipes. If you have brown sugar, use that and omit the molasses.
Substitute kefir with buttermilk, half yogurt half milk, whey, or clabber. Fermented milk helps the fresh milled flour to soften and fluff after baking!
Sub pineapple rings and chunks for the mock zucchini pineapple. Do whatever you want… you can’t have too much pineapple :D
Equipment
- 9-inch round cake pan
- Cooling Racks
- stand mixer
- Mixing bowl with a lid
Ingredients
Topping
Cake
- 3 Tbs butter room temp
- 3/4 cup sugar
- 4 quail eggs or 1 chicken egg
- 1/2 tsp salt
- 2 tsp vanilla extract
- 1 1/2 cup fresh milled soft white wheat chilled
- 2 Tbs cornstarch
- 1/2 cup milk kefir
- 1 3/4 cup baking powder
Instructions
- To the bowl of your stand mixer, add the butter, sugar, and molasses. Beat until smooth, this takes a few minutes. Stop to scrape the bottom of the bowl once or twice.
- Mix in the eggs, salt, and vanilla extract.
- Mix the fresh milled soft white wheat and cornstarch together. Add about 1/3 of the flour, followed by 1/2 of the kefir, alternating once more and ending with a final addition of the flour mixture. Mix only until smooth. Scrape the bottom of the bowl and sides down and hand mix if needed.
- Transfer batter to a bowl with a tight fitting lid and allow to sit and rest a minimum of 30 minutes, but preferably about 12 hours.
- Start by grease the 9-inch round cake pan with ghee.
- Preheat oven to 375 degrees F.
- Make the topping: In a sauce pan, melt the butter, sugar, molasses, cinnamon, and ginger. Pour into the prepared cake pan.
- Evenly scatter the mock pineapple zucchini and maraschino cherries on the bottom of the pan. You can also use pineapple chunks or rings in place of the mock pineapple zucchini to be extra pretty like I did in the recipe photo.
- After resting, stir in the baking powder, mixing to incorporate and being careful not to overmix. The batter will be very thick. Spoon the batter overtop of the caramel and pineapple. Press to spread out as well as you can but it’s okay if it doesn’t go completely to the edges.
- Bake the cake for 30 minutes, or til a toothpick inserted into the center comes out clean. Ovens vary!
- Once cake is done, remove from oven to a cooling rack. Run a knife around the edge of the pan carefully and allow the cake to cool for 3-5 minutes.
- Turn the pan over onto a serving plate and gently tap the bottom of the cake pan. Wait about 30 seconds and lift the pan off. If it sticks lift the pieces out of the pan and place it back on the cake… it’ll taste just fine. Promise.
- Let cool, and serve warm or at room temperature. Once cooled, wrap tightly or place in an air tight container to prevent the cake from drying out. Fresh milled flour baking likes to dry out much faster than dead flour!
