This Chocolate Cherry Upside Down Cake is a delightful twist on the traditional pineapple version, combining rich chocolate cake with the sweet-tart flavor of cherries. When inverted, the gorgeous cherry topping reveals itself, creating a show-stopping dessert that’s both elegant and comforting. Perfect for special occasions or weekend treats, this cake balances decadent chocolate with fruity brightness in every bite.

Why You’ll Love This Recipe

• Impressive presentation with minimal effort – the upside-down technique creates a beautiful top layer automatically
• Perfect balance of rich chocolate and sweet-tart cherries
• Uses convenient ingredients like boxed cake mix and canned cherry filling
• Can be served warm or at room temperature, making it flexible for any occasion
• Simple enough for beginners but impressive enough for special celebrations

Ingredients

• Cherry Pie Filling: The star of the show that creates a gorgeous, jewel-toned top layer. The sweet-tart cherries balance perfectly with the chocolate cake.
• Butter: Unsalted butter works best so you can control the salt content. The melted butter combines with brown sugar to create a caramel-like topping.
• Brown Sugar: Creates a delicious caramelized flavor when combined with butter. Light or dark brown sugar will work, though dark will give a more robust molasses flavor.
• Chocolate Cake Mix: A convenient shortcut that provides consistent results. Any brand works well, but devil’s food or dark chocolate varieties offer the richest flavor.
• Eggs: Provide structure and richness to the cake. Make sure they’re at room temperature for the best incorporation.
• Vegetable Oil: Keeps the cake moist and tender. You can substitute canola oil or melted coconut oil if preferred.
• Water: Helps thin the batter to the right consistency. You can substitute coffee for a deeper chocolate flavor.
• Vanilla Extract: Enhances the overall flavor profile. Pure vanilla extract gives the best flavor, but imitation works in a pinch.

Variations

Black Forest Inspired

Transform this into a Black Forest-inspired dessert by adding a teaspoon of kirsch (cherry liqueur) to the cherry topping. After inverting, top with whipped cream and chocolate shavings for the complete Black Forest experience.

White Chocolate Cherry

Swap the chocolate cake mix for a white or vanilla cake mix, and add 1 cup of white chocolate chips to the batter. The contrast between the white cake and red cherries creates a stunning visual effect.

Mixed Berry Chocolate

Replace half the cherry pie filling with mixed berry pie filling or fresh berries (strawberries, raspberries, blackberries) for a more complex fruit flavor that still pairs beautifully with the chocolate cake.

How to Make the Recipe

Step 1: Prepare the Cherry Layer

Preheat your oven to 350°F (175°C) and grease a 9×13-inch baking pan thoroughly to prevent sticking. Pour the melted butter into the bottom of the pan, making sure it coats evenly. Sprinkle the brown sugar uniformly over the butter to create a caramelized base. Gently spread the cherry pie filling over the brown sugar layer, being careful to distribute the cherries evenly.

Step 2: Mix the Cake Batter

In a large mixing bowl, combine the chocolate cake mix, eggs, vegetable oil, water, and vanilla extract. Beat with an electric mixer on medium speed for about 2 minutes until the batter becomes smooth and well-combined. Make sure to scrape down the sides of the bowl to incorporate all dry ingredients.

Step 3: Assemble and Bake

Carefully pour the cake batter over the cherry layer, using a spatula to spread it evenly without disturbing the cherry layer underneath. Bake in the preheated oven for 35-40 minutes, or until a toothpick inserted into the center comes out clean with just a few moist crumbs. The cake should spring back when lightly touched.

Step 4: Invert and Serve

Allow the cake to cool in the pan for exactly 10 minutes – not too long or it may stick, but not too short or it may fall apart. Place a large serving platter or cutting board over the top of the baking pan. Holding the platter and pan together firmly, quickly flip them over so the cake releases onto the platter with the cherry side on top. Gently remove the pan and let the cake cool further before slicing.

Tips for Making the Recipe

• Let the melted butter cool slightly before adding the brown sugar to prevent it from melting too quickly
• For the best cherry distribution, gently spread the pie filling with the back of a spoon rather than stirring it
• Don’t overmix the cake batter – mix just until ingredients are combined to keep the cake tender
• Place a baking sheet under your cake pan in the oven to catch any potential overflow
• Let the cake cool for exactly 10 minutes before inverting – too short and it might fall apart, too long and it might stick
• If any cherries stick to the pan after inverting, simply scrape them off and place them back on the cake

How to Serve

This Chocolate Cherry Upside Down Cake is best served slightly warm or at room temperature. For an extra-special presentation, dust the top with powdered sugar just before serving or add a dollop of whipped cream on each slice. For a more decadent dessert, serve with a scoop of vanilla ice cream or a drizzle of warm chocolate sauce. This cake pairs wonderfully with coffee, tea, or a glass of dessert wine for adult gatherings.

Make Ahead

This cake can easily be made 1-2 days in advance. After cooling completely, cover loosely with foil (avoid plastic wrap as it might stick to the cherry topping) and store at room temperature for up to 2 days. For longer storage, refrigerate for up to 5 days, though the cake texture may become slightly more dense.

If you want to prepare components ahead of time, you can mix the dry ingredients for the cake and store them in an airtight container until ready to use. The cherry layer should be prepared just before assembling and baking for the best results. Individual slices can be frozen for up to 3 months – wrap each piece in plastic wrap and then foil before freezing.

FAQs

Can I use fresh cherries instead of canned pie filling?

Yes, you can use about 4 cups of fresh pitted cherries mixed with 1/3 cup sugar and 2 tablespoons cornstarch (cook until thickened). However, canned filling provides consistent results and saves significant time.

Why did my cake stick to the pan when inverting?

This usually happens if the cake cooled too long in the pan. Make sure to invert after exactly 10 minutes of cooling. Also, be sure to grease the pan thoroughly before starting.

Can I make this cake gluten-free?

Absolutely! Simply substitute a gluten-free chocolate cake mix. The other ingredients are naturally gluten-free, but always check labels to be sure.

How do I know when the cake is done baking?

Insert a toothpick into the center of the cake (not into a cherry). It should come out clean or with a few moist crumbs, but not wet batter. The cake should also spring back when lightly touched in the center.

Conclusion

This Chocolate Cherry Upside Down Cake combines convenience with impressive results, making it perfect for both novice bakers and experienced cooks. The dramatic presentation of glossy cherries atop rich chocolate cake never fails to impress, while the balanced flavors ensure it’s as delicious as it is beautiful. Whether you’re hosting a dinner party, celebrating a special occasion, or simply treating yourself to something special, this cake delivers maximum impact with minimal effort. Try it once, and it may just become your new go-to dessert for any occasion!

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