Chocolate Cherry Upside Down

This chocolate cherry upside-down cake transforms humble ingredients into a showstopping dessert that balances rich chocolate with bright, sweet cherries. The dramatic reveal when you flip the cake creates that perfect "wow" moment every time I serve it to guests.

I first made this cake for my sister's birthday when I was in a pinch for time. The look on her face when I flipped over the cake to reveal those glossy cherries nestled in caramel convinced me this recipe needed to become part of my regular rotation.

Ingredients

• Cherry pie filling: Provides convenience while delivering intense fruit flavor
• Melted butter: Creates that signature caramelized edge around each cherry
• Brown sugar: Develops into a rich caramel that balances the tartness of cherries
• Chocolate cake mix: Saves time without sacrificing quality
• Large eggs: Provide structure and richness to the cake base
• Vegetable oil: Ensures the cake stays moist for days
• Water: Thins the batter to the perfect consistency
• Vanilla extract: Enhances the chocolate flavor while complementing the cherries

Step-by-Step Instructions

Prepare the Topping:

Position your oven rack in the center and preheat to 350°F. Thoroughly grease your 9×13 baking pan ensuring you get into all corners. Pour melted butter across the entire bottom surface watching it spread evenly. Sprinkle brown sugar in an even layer over the butter using your fingers to break up any clumps. Spoon cherry pie filling carefully over this mixture ensuring even coverage.

Make the Cake Batter:

In a large bowl combine cake mix eggs oil water and vanilla. Start your mixer on low speed to prevent a dust cloud from the dry ingredients. Gradually increase to medium speed beating for exactly 2 minutes until the batter becomes smooth and silky with no visible dry pockets.

Assemble the Cake:

Hold your bowl about 6 inches above the cherry layer and slowly pour the batter starting from the center moving outward in a spiral pattern. Use a silicone spatula to gently spread the batter to the edges being careful not to disturb the cherry layer beneath.

Bake:

Place the pan on the center rack and bake for 35 minutes. Check by inserting a toothpick in several places near the center. The toothpick should come out with a few moist crumbs but no wet batter. If needed bake for additional 3 minute increments.

Cool and Invert:

Set a timer for exactly 10 minutes after removing the cake from the oven. Place your serving platter over the top of the cake pan. Holding the platter and pan firmly together flip them in one quick confident motion. Leave the pan in place for 30 seconds allowing gravity to help release the cake. Lift the pan straight up to reveal the beautiful cherry topping.

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My absolute favorite part of this cake is when the brown sugar and butter transform into that caramel sauce during baking. I still remember my daughter asking if we could just eat the "magic top" after her first bite as a toddler. Now she helps me make it and still licks the spoon after spreading the cherry filling.

Storage Secrets

This cake maintains optimal freshness when stored at room temperature in an airtight container for up to three days. The moisture from the cherries keeps the cake from drying out making it one of those rare desserts that actually improves with time. If storing longer than three days refrigerate but allow slices to come to room temperature before serving to maximize flavor.

Flavor Variations

While cherry is the classic choice for this upside-down cake you can easily substitute other canned pie fillings like blueberry peach or strawberry depending on seasonal preferences. For a more adult version try adding 2 tablespoons of kirsch or amaretto to the cherry mixture before spreading it in the pan. The alcohol cooks off leaving behind complex flavor notes that elevate the entire dessert.

Serving Suggestions

This cake reaches ultimate decadence when served slightly warm with a scoop of vanilla bean ice cream melting into the cherry topping. For breakfast or brunch servings pair with freshly whipped cream and a sprinkle of chocolate shavings. During the holidays I serve this with a cinnamon-spiced whipped cream and a touch of shaved dark chocolate for an elegant presentation.

Frequently Asked Questions

→ How do I store the cake?

Store the cake in an airtight container at room temperature for up to 3 days. To keep it fresher longer, refrigerate for up to a week.

→ Can I use fresh cherries instead of canned pie filling?

Yes, you can use fresh cherries. Cook them with sugar and cornstarch until thickened to substitute for the pie filling.

→ What can I serve with this cake?

Serve it with vanilla ice cream or whipped cream for an extra indulgent treat.

→ Can I use a different cake mix flavor?

Absolutely! While chocolate complements cherries well, you can experiment with yellow or vanilla cake mix for a different twist.

→ Do I need to grease the baking pan?

Yes, greasing the pan is essential to prevent sticking and to ensure the cake inverts cleanly.

→ What’s the best way to invert the cake?

Cool the cake for about 10 minutes, place a platter over the pan, and carefully flip it upside down to release the cake with its cherry topping intact.