Chocolate Cherry Upside Down Cake

This chocolate cherry upside-down cake transforms a box of cake mix into a bakery-worthy dessert with minimal effort. The cake bakes with cherries on the bottom, then gets flipped to reveal a gorgeous, glossy fruit topping that makes everyone think you spent hours in the kitchen. I discovered this recipe during cherry season last summer and it's become my secret weapon for last-minute dinner parties.

I initially made this for my daughter's birthday when I ran out of time to make the elaborate cake I'd promised. The family was so impressed they now request this "fancy" cake over any bakery option.

Ingredients

• Canned cherry pie filling gives you consistent results year round without the work of pitting fresh cherries
• Melted butter creates that caramelized magic when it combines with the brown sugar
• Brown sugar adds a rich molasses note that pairs perfectly with chocolate and cherries
• Chocolate cake mix saves tremendous time while still providing a moist base
• Large eggs provide structure and richness to elevate the boxed mix
• Vegetable oil keeps the cake incredibly moist for days
• Water thins the batter to the right consistency
• Vanilla extract enhances both the chocolate and cherry flavors

Step-by-Step Instructions

Prepare the Pan

Preheat your oven to 350°F and thoroughly grease your 9×13 baking pan making sure to get into all corners. Pour melted butter evenly across the bottom the hot butter helps dissolve the brown sugar creating the caramel effect. Sprinkle brown sugar in an even layer this will caramelize during baking to create that signature upside down cake glaze. Carefully spoon the cherry pie filling evenly over the butter and sugar layer ensuring good coverage across the entire pan.

Make the Batter

In a large mixing bowl combine the chocolate cake mix eggs oil water and vanilla. Begin mixing on low speed for 30 seconds to incorporate the dry ingredients without creating a dust cloud. Increase to medium speed and beat for 2 full minutes this develops the structure that will support your cherries after flipping.

Assemble and Bake

Gently pour the cake batter over the cherry layer being careful not to disturb the fruit too much. Use a spatula to carefully spread the batter into an even layer covering all cherries. Bake in the preheated oven for exactly 35 minutes then check with a toothpick inserted into the center if it comes out with moist crumbs not wet batter it's done.

The Flip

Allow the cake to cool for exactly 10 minutes in the pan any longer and the caramel might stick any less and the cake might fall apart. Place your serving platter upside down on top of the cake pan then in one confident motion flip the cake over. Wait 30 seconds before slowly lifting the pan to reveal your masterpiece.

The brown sugar caramel layer is what makes this cake truly special. The first time I made it, my mother-in-law actually accused me of buying it from a bakery. Now it's my signature dessert for family gatherings, and I've never told her how simple it really is to make.

Serving Suggestions

This cake reaches peak deliciousness when served slightly warm with a scoop of vanilla ice cream melting into the cherry topping. The contrast between the warm cake and cold ice cream creates a sensory experience that elevates the dessert to restaurant quality. For special occasions, add a light dusting of powdered sugar just before serving to create a snow-like effect against the deep red cherries.

Make It Your Own

While cherry and chocolate create a classic pairing, this versatile recipe works beautifully with other fruit fillings. Try blueberry pie filling with a yellow cake mix for a summery variation, or apple pie filling with a spice cake mix for autumn gatherings. You can also enhance the chocolate flavor by substituting strong brewed coffee for half of the water in the cake mix, which intensifies the chocolate notes without adding coffee flavor.

Storage Tips

If you manage to have leftovers, store them covered at room temperature for up to three days. The moisture from the fruit keeps the cake from drying out, making it just as delicious on day three as it was when fresh. For longer storage, cut individual slices and freeze them wrapped tightly in plastic wrap and foil. Thaw at room temperature for about an hour before serving, or microwave for 20-30 seconds for that just-baked warmth.

Bookmark

Recipe FAQs

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

Yes, you can substitute fresh cherries. Pit about 2 cups of cherries and cook them with 1/4 cup sugar and 1 tablespoon cornstarch until thickened. Cool before using in the cake.

→ How do I prevent the cake from sticking when I flip it?

Ensure your pan is well-greased, especially the sides. Let the cake cool for exactly 10 minutes—not too long or too short—before inverting. Run a knife around the edges before flipping onto a serving plate.

→ Can this cake be made in advance?

Yes, you can make it 1-2 days ahead. Store at room temperature for one day or refrigerate for up to three days. The flavors actually deepen over time.

→ What other fruit variations work with this cake?

This versatile cake works well with other fruits like pineapple, peaches, plums, or berries. Just ensure the fruit isn't too watery to prevent a soggy cake.

→ Do I need to use a chocolate cake mix or can I make it from scratch?

You can absolutely use a homemade chocolate cake batter instead. Any basic chocolate cake recipe that yields enough batter for a 9×13-inch pan will work perfectly.

→ How should I serve this cake?

Serve slightly warm or at room temperature. It pairs beautifully with vanilla ice cream, whipped cream, or a light dusting of powdered sugar.