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Chocolate Cherry Upside Down Cake is my go-to when I want a showstopper everybody’s happy to dig into. The bottom becomes a thick, chocolatey base that soaks up all that jammy cherry goodness as it bakes. Whenever someone’s having a birthday or we’re grilling out in the backyard, I whip this up and—honestly—it’s wiped out every single time.
I first tried making this when my oldest walked in begging for something with both cherries and chocolate. The taste knocked our socks off on that first bite, and now she won’t hear of any other treat at family parties.
Irresistible Ingredients
- Vanilla extract: softens the flavors and gives a sweet aroma whenever possible use the real thing
- Water: ties the batter together cold filtered water works best for a smooth pour
- Vegetable oil: holds onto moisture in every bite a neutral pick like canola is perfect
- Large eggs: keep everything together and give your cake structure
- Chocolate cake mix: makes things easy and ensures nice height spring for a good quality mix for a bold chocolate flavor
- Brown sugar: adds depth and lots of caramelly flavor in the cherry layer darker sugar gives even more richness
- Unsalted butter: creates a buttery top layer once melted use fresh sticks for the best flavor
- Cherry pie filling: bursts with sweet-tart fruit and forms that signature sticky surface whole cherries give the best pop
Simple Steps
- Cool and Flip
- Wait ten minutes after baking before you turn the pan over so the cherries stay put Run a knife around the edges to loosen everything Set a big plate over the pan and quickly flip—cherries will end up on top Serve warm for a soft cake or after it cools for clean slices
- Bake and Build Layers
- Gently pour the chocolate batter on top of the fruit and spread out so the cherries stay in place Pop the pan into the oven’s center rack Bake for thirty five to forty minutes Check at the early mark with a toothpick—it’s baked when just a few damp crumbs stick to it
- Chocolate Batter Mix
- In a large bowl drop in the eggs, then add water, oil, vanilla, and cake mix Mix by hand or with a beater just until you can’t see flour and everything looks shiny and smooth
- Cherry Layer Prep
- Pour the melted butter over your pan tilting so every section gets covered Sprinkle brown sugar over all that butter, then spread cherry filling across the top so no spot is missed
- Pan Ready
- Fire up your oven to 350 degrees Fahrenheit Use butter or spray to coat a 9 by 13 inch pan, making sure no corner’s missed so it all comes out easy
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Good to Keep in Mind
- You can make it ahead and gently warm leftovers the next day—it still stays moist
- No matter the season, you’re set since you’re using canned cherries
- No nuts anywhere and you can switch butter for a vegan option if you want it dairy free
The gooey cherry layer is the absolute best bit—bubbling as you pull the cake from the oven, filling the house with a cozy smell. Whenever family’s over, the crispy corners always go first for that extra hit of cherry.
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Keeping It Fresh
Just cover up leftover cake with foil or throw pieces into a container and they’ll be good on the counter for up to three days. Want it to last longer? Stick it in the fridge and it’ll stay nice for about five days. Warm it up a bit before serving for the best flavor.
Switching It Up
If you’re out of cherry filling, canned peaches or apple filling work instead. Coconut oil swaps in smoothly for butter if you’re not doing dairy—just peek at your cake mix for allergens. Chocolate chips stirred into the batter add extra decadence if you’re in the mood.
Ways to Serve
A scoop of vanilla ice cream or some whipped cream takes this over the top. Or just give it a sprinkle of powdered sugar or a swirl of chocolate sauce. Eat it fresh out of the oven if you love a gooey cherry layer or let it sit for tidier slices.
Backstory
Upside down cakes started showing up in American kitchens as soon as canned fruit was easy to grab. This chocolate cherry version is a fun update on old-school pineapple and it’s always a hit at potlucks and get-togethers with friends.
FAQs About the Recipe
- → Is it okay to swap in fresh cherries for the canned filling?
You sure can, just pit and simmer them with a bit of sugar and cornstarch first so they get nice and sticky, like classic pie filling.
- → How will I know the cake’s baked all the way?
Poke the middle with a toothpick—if you pull it out and only see a couple crumbs or nothing at all, you're good. The top should bounce back when you press it.
- → What’s a good way to flip this cake without it crumbling?
Wait about 10 minutes before flipping. Put a big plate over the cake pan and turn it over fast, holding on tight. If it sticks, give it a little tap until it drops out.
- → Can I prep this ahead of time?
Definitely. Leave it in a sealed container on your counter for up to three days. Warm slices in the microwave if you want it cozy again.
- → What do you recommend for topping?
A scoop of vanilla ice cream or a dollop of whipped cream really takes this over the top. Creamy and cool with that deep chocolate? Total win.