Best Chocolate Caramel Cupcakes Recipes

CHOCOLATE CUPCAKES WITH SALTED CARAMEL FROSTING AND CHOCOLATE FUDGE FILLING

Steps:

• For the chocolate cupcakes: Preheat the oven to 350 degrees F. Line a 24-cup muffin pan with cupcake liners.
• Cream the granulated sugar, butter and oil in a large bowl. Beat in the eggs, one at a time, until fluffy. Add the vanilla and blend well. Sift the flour, baking soda and sea salt and gradually add to the sugar mixture, alternating with the milk.
• Whisk the cocoa and water until smooth in a small bowl. Add to the mixture and continue beating until well blended.
• Fill each muffin cup three-quarters full with batter. Bake the cupcakes until baked through the center, about 15 minutes. Remove the cupcakes from the pan and cool on wire racks.
• For the chocolate fudge filling: Melt the butter in a microwave-safe bowl. Whisk the cocoa and water until smooth in a separate bowl. Whisk the cocoa mixture into the butter until blended and smooth. Whisk in the powdered sugar until fluffy. Yield: 2 cups.
• For the buttercream base frosting: Whip the powdered sugar, milk, vanilla and sea salt with a whisk attachment on low until smooth and creamy. Add the butter one slice at a time until well blended. Add the shortening and blend well. Whip on high until the mixture doubles, 10 to 12 minutes. Yield: 8 cups.
• For the salted caramel: Combine 1/4 cup room temperature water and the granulated sugar in a small saucepan. Cook over medium-low heat until the sugar dissolves. Increase the heat to medium-high and bring to a boil. Boil without stirring, until the mixture is approximately 325 degrees F and a deep amber color, 5 to 6 minutes.
• Remove the caramel from the heat and whisk in the cream. The caramel will bubble violently. Once smooth, stir in the butter and fine sea salt. Transfer the caramel to a heat safe container and allow cooling for 15 minutes. Cover and refrigerate for up to 2 weeks. Yield: 1 1/2 cups.
• For the salted caramel frosting: Whip 2 1/2 cups buttercream base frosting, the powdered sugar and 1/2 cup salted caramel with a whisk attachment until fluffy. Yield: 3 cups.
• Once the cupcakes are cool, cut out the center of each cupcake and fill with the chocolate fudge filling. Top each cupcake with the salted caramel frosting.

SKY-HIGH SALTED CARAMEL CHOCOLATE CUPCAKES

Steps:

• Heat oven to 375°F. Place paper baking cup in each of 24 regular-size muffin cups. Make cupcakes as directed on box; cool completely on cooling rack, about 30 minutes.
• Meanwhile, in medium bowl, beat Salted Caramel Cheesecake Filling ingredients with electric mixer on medium speed just until smooth and well combined. Using melon baller, scoop out center of each cupcake about 1 inch deep. Fill each cupcake with 1 tablespoon filling.
• To make Salted Caramel Buttercream: In large bowl, beat butter with electric mixer on low speed until smooth. Gradually add powdered sugar, 1 cup at a time, beating until combined; beat in vanilla. In large microwavable bowl, microwave caramels and 1 tablespoon of the milk uncovered on High about 1 minute or until caramels are melted; stir until smooth. Stir caramel mixture and kosher salt into buttercream mixture until combined, adding remaining milk until smooth and spreadable.
• In small bowl, mix chopped pecans and crushed pretzels. Place buttercream in large decorating bag fitted with large open star tip. Frost 1 cupcake at a time with buttercream, then roll immediately in pecan mixture. Repeat with remaining cupcakes, frosting and rolling in pecan mixture.
• Drizzle cupcakes with caramel topping. Sprinkle with additional kosher salt. Refrigerate until ready to serve. Serve with ice cream, if desired.

GEORGE CARAMELIN: CHOCOLATE CINNAMON CUPCAKES WITH VANILLA BEAN BOURBON FROSTING, BOURBON CARAMEL SAUCE, AND CANDIED PECANS

Steps:

• For the cupcakes: Preheat the oven to 325 degrees F. Line standard cupcake pans with 18 cupcake liners.
• Sift the sugar, flour, cocoa, cinnamon, baking soda, and salt into a medium bowl. Set the bowl aside. In a small bowl, whisk together the coconut milk, coffee, oil, and vanilla. Add the wet ingredients to the dry ingredients and whisk until just incorporated. Add vinegar and incorporate. Do not over mix the batter.
• Fill the cupcake liners 3/4 full and bake until a toothpick inserted into each cupcake comes out clean, 19 minutes. Cool the cupcakes completely.
• For the sauce: In a small, heavy-bottomed saucepan, stir together the sugar and water. Cover and bring to a boil. Let boil until the mixture starts to turn brown, about 20 minutes. Remove from the heat and stir with a whisk. Add the bourbon and salt and continue stirring. Once the bubbling stops, add the margarine and whisk until melted and distributed. Let cool completely and pour into a clean squirt bottle.
• For the pecans: In a large bowl, toss the pecans with the melted margarine until all the pecans are coated. In a separate bowl, mix the cinnamon, sugar, and sea salt. Toss into the pecan mixture and coat evenly. Spread the pecans out on a baking sheet lined with parchment paper, making sure the pecans are not overlapping. Bake for 6 to 8 minutes. Let cool completely.
• For the frosting: In the bowl of a stand mixer, whip the shortening and margarine until completely combined. Scrape the bottom of the bowl to ensure that all ingredients are mixed thoroughly. On low speed, slowly add the sugar a little at a time. Once the sugar is incorporated, add the vanilla paste and bourbon and mix on low until the liquids are incorporated. Scrape the bottom of the bowl and mix on medium-high speed until all the ingredients are combined and the frosting is fluffy, about 2 minutes. Put the frosting into a pastry bag fitted with a large star tip.
• To assemble: With a plastic drinking straw or a small paring knife, make holes in the center of each cupcake. Squeeze the bourbon caramel sauce into the center of the cupcake until filled but not overflowing, about 1 tablespoon per cupcake. Pipe a dollop of vanilla bean bourbon frosting onto of each cupcake. Drizzle the top with more bourbon caramel sauce and sprinkle with candied pecans to garnish.

CHOCOLATE CARAMEL CUPCAKES

Steps:

• Prepare cake mix batter according to package directions for cupcakes. Fill 24 paper-lined muffin cups one-third full; set remaining batter aside. Bake at 350° for 7-8 minutes or until top of cupcake appears set., Gently press a caramel into each cupcake; sprinkle with chocolate chips and walnuts. Top with remaining batter. Bake 15-20 minutes longer or until a toothpick comes out clean. , Cool for 5 minutes before removing from pans to wire racks to cool completely. Frost with chocolate frosting and drizzle with ice cream topping. Sprinkle with additional nuts if desired.

VEGAN CHOCOLATE GANACHE CUPCAKES WITH SALTED CARAMEL AND DARK CHOCOLATE BUTTERCREAM

Steps:

• For the cupcakes: Preheat the oven to 325 degrees F. Line standard-size cupcake pans with 16 cupcake liners.
• In a medium bowl, whisk together the soy milk, agave nectar, canola oil, cane sugar, vanilla extract and apple cider vinegar, and set aside. In a large bowl, sift the flour, cocoa powders, baking powder, baking soda and salt and whisk them together. Add your wet mixture to the dry and whisk until the mixture is evenly moist and only a few lumps remain. Set aside.
• For the ganache: Whisk together the chocolate chunks, soy milk and agave nectar in a microwave-safe bowl. Place the bowl into a microwave and heat for 1-minute increments, whisking in-between, until the mixture is thick and smooth.
• Take your cupcake batter and start to stream in about 1 cup of the chocolate ganache and gently fold it into the batter. Do not fully mix it into the batter, it should be swirled in.
• Fill the liners three-quarters full and bake until a toothpick comes out clean, 12 to 15 minutes. Cool the cupcakes completely.
• For the salted caramel sauce: In a nonstick saucepan, add the coconut milk fat. Add in the brown sugar, vanilla and salt, and whisk well. Bring the mixture to a boil on medium-high heat, whisking occasionally. Once the mixture starts to boil, reduce the heat to a low bowl and cook for 35 to 45 minutes, whisking every couple of minutes, until the sauce has reduced by half. The resulting mixture will be thick and golden. Allow the caramel to cool slightly and use immediately.
• For the buttercream: Whip the shortening and margarine together in a mixer bowl with the paddle attachment until fluffy. Scrape down the bowl and put back onto the mixer on low-speed and slowly add the powdered sugar and cocoa powder. Once the mixture is fully incorporated, stream in 1 cup of the chocolate ganache. Once the ganache is added, you may turn the mixer to medium-high and whip until the buttercream is very fluffy.
• To assemble: Poke a hole in the center of each cupcake using the end of a wooden spoon or small offset spatula. Fill the hole completely with salted caramel sauce. Using a round frosting tip, generously frost the top of each cupcake with the dark chocolate buttercream. Drizzle the top of each cupcake with more salted caramel sauce.

CHOCOLATE SALTED CARAMEL CUPCAKES

Steps:

• For the cupcakes: Preheat the oven to 345 degrees F. Line a cupcake pan with liners.
• Combine the sugar, flour, cocoa powder, baking powder and baking soda in a bowl. In a small pot over low heat warm up 1 cup water, the butter and espresso. Do not boil! Just melt the butter. Set aside to cool.
• Combine the buttermilk, eggs and coffee mixture in a second bowl. Combine the wet ingredients with the dry ingredients and mix with a whisk until smooth.
• Scoop the batter into the cupcake liners and bake for 10 to 12 minutes. Check for doneness by inserting a toothpick into the cupcakes. If it comes out clean, they are done. Allow to cool.
• For the ganache: In a small pot over low heat, mix the chocolate and cream until combined and smooth. Take off the heat. Add the coffee liqueur if using and mix.
• To assemble: Using a apple corer or a small spoon, scoop a small well halfway through in the center of the cupcakes. Spoon 1 teaspoon of the ganache into the well, as well as brush some over the top of the cupcakes. Fill a pastry bag with piping tip of your choice with Salted Caramel Buttercream. Pipe the buttercream directly on top of the cupcakes. Garnish as you please.
• Slowly heat the cream in a small pot over low heat.
• While heating up the cream, in another pot over medium heat, add one third of the sugar and the salt and mix with a wooden spoon until liquid. Continue to add the remainder of the sugar in one-third increments. Once all the sugar is dissolved, continue to mix the caramel until it reaches a slightly darker brown color.
• Turn off the heat and add the hot cream very slowly in increments while stirring. Be very careful to not burn yourself! Caramel is ready once the cream and caramel are smooth. Transfer to a bowl for cooling. Allow 1 hour to cool at room temperature.
• Add the cooled caramel mixture to a mixing bowl and with a paddle attachment on medium speed, add the butter in increments. Once the buttercream is smooth it is ready to be used.

CHOCOLATE CUPCAKES WITH SALTED CARAMEL CENTER SURPRISE

Steps:

• Heat oven to 350°F. Place paper baking cup in each of 18 regular-size muffin cups. Make cake batter as directed on box. Fill muffin cups about 3/4 full. Place caramel onto center of batter in each cup; press caramel into batter just until covered.
• Bake 20 to 25 minutes or until tops spring back when touched lightly in center. Cool in pans 10 minutes; remove from pans to cooling rack. Cool completely, about 30 minutes.
• Place frosting in decorating bag fitted with round tip #20. Starting at outer edge of cupcakes, pipe frosting in spiral pattern, gradually elevating to a peak in center; garnish with pretzels.

COCONUT CUPCAKES WITH CHOCOLATE GANACHE FILLING, TOPPED WITH CARAMEL BUTTERCREAM FROSTING AND TOASTED COCONUT

Steps:

• Preheat the oven to 325 degrees F. Line a regular-size cupcake pan with 18 cupcake liners.
• Sift together flour, baking powder, salt, and sugar. In the bowl of an electric stand mixer with a paddle attachment, add the sifted dry ingredients and mix on low speed for 30 seconds. Slowly add oil to the mixture until fine crumbs are formed. Add the eggs, milk, and coconut extract and mix on low speed for 1 minute. Stop and scrape the bowl and paddle, and then mix on medium speed for 2 minutes.
• Fill the cupcake liners three-quarters full with batter and bake until baked through, about 20 minutes. Do not open the oven during this time. Cool the cupcakes completely after baking.
• To assemble, core each cupcake with an apple corer to create a pocket for the filling. Put the Chocolate Ganache Filling into a pastry bag and cut 1/2-inch off the tip. Fill each cupcake with the filling. Put the Caramel Buttercream Frosting into a pastry bag and cut 1/2-inch off the tip. Pipe the frosting on top of the cupcakes in a circular motion until completely covered. Once frosted, dip the cupcakes in a bowl of the toasted coconut and serve.
• Melt the ingredients in a saucepan over low heat. Stir the mixture constantly until melted and smooth. Be careful not to burn. Remove from the heat to cool completely.
• Stir 1 cup butter, heavy cream, brown sugar, white sugar, and vanilla together in a microwave-safe dish. Microwave at 1 to 2 minute intervals, stirring between intervals. The caramel will be thick and bubbly when done. The caramel must sit and cool completely in order to incorporate into the buttercream.
• In the bowl of an electric stand mixer with a whisk attachment, whip the remaining 1 pound butter until creamed. Add the powdered sugar and 1/4 cup cooled caramel and mix until the ingredients are evenly incorporated and the frosting is smooth and creamy.

CHOCOLATE BANANA CUPCAKES WITH PEANUT BUTTER CARAMEL BUTTERCREAM

Steps:

• Cupcakes: To make the cupcakes: Preheat oven to 350 F. Line a muffin tin with paper liners. In a medium bowl, whisk the mashed banana, heavy cream, sugar, oil and vanilla until well combined. The mixture won't be completely smooth, but mix vigorously to get out as many of the large lumps as possible. In a second medium bowl, whisk the flour, cocoa powder, baking soda, baking powder and salt together. (Sift your cocoa into this mixture if it appears clumpy). Add the dry ingredients to the bowl with the wet ingredients and gently whisk (or fold with a rubber spatula) until flour just disappears. Distribute the batter evenly among the liners, filling each about 1/2 - 2/3 full (an ice cream scoop works great for this). Bake for 18-20 minutes, or until the cupcakes spring back when lightly touched and a toothpick inserted in the center comes out clean. Remove the muffin pan to a wire rack. Let the cupcakes cool in the pan for 5 minutes then transfer them to the wire rack to cool completely. Buttercream: In a stand mixer fitted with the whisk attachment (I used the paddle because I'm a rebel. Or I don't read the recipe well enough), beat butter and peanut butter at medium-high speed until smooth, about a minute. Add the confectioners' sugar and salt to the bowl and beat at low speed just until the sugar is moistened, about 30 seconds. Scrape down the sides of the bowl and beat the mixture on med-high until fully combined. You'll notice it taking on a lighter color and a more uniform texture, this is perfect. Finally, mix in the vanilla and caramel sauce and beat on med-high to incorporate. Scrape down the sides of the bowl again then beat on medium speed until the frosting is light and fluffy. Pipe the frosting onto the cooled cupcakes and garnish with caramel drizzle, melted chocolate or anything your heart desires.

CHOCOLATE PRETZEL CUPCAKES WITH CARAMEL FROSTING

Steps:

• Preheat the oven to 350°F and prepare cupcakes according to package directions. Cool completely before proceeding.
• In a piping bag, add thick stripes of caramel to the sides of the bag before spooning in the chocolate frosting. This will give a caramel swirl when the frosting is piped onto the cupcake. Pipe frosting onto all cupcakes.
• Crush mini pretzels to sprinkle over the top of the frosting. Garnish each cupcake with one whole mini pretzel.

CHOCOLATE PORTER CUPCAKES, PORTER GANACHE, CARAMEL CORN CRUNCH, TOASTED MERINGUE

Steps:

• For the cupcakes: Preheat the oven to 350 degrees F. Line a mini cupcake pan with 12 cupcake liners.
• Sift the flour, baking soda and salt into a medium bowl. Set the bowl aside.
• In the bowl of an electric stand mixer with a paddle attachment, cream the sugar and oil together, about 5 minutes. Scrape down the sides of the bowl, and then add the vanilla and coffee extracts and 1 egg at a time, scraping down the sides of the bowl after each addition.
• Whisk your porter beer and cocoa together in a separate bowl and set aside.
• Turn the mixer to low and add your sour cream. Continue with the mixer on the lowest speed and add the flour mixture and cocoa mixture, alternating between the two, beginning and ending with the flour.
• Fill the prepared liners half full with the batter and bake for 30 minutes. Cool.
• For the ganache: In a microwave-safe bowl, heat the porter beer to 130 degrees F. Pour the beer over the white chocolate in a clean medium bowl. Whisk until incorporated. Transfer the ganache into a sauce bottle for use. Hold at room temperature until the cupcakes are cooled.
• For the caramel corn crunch: In a microwave-safe bowl, heat your peanut butter and milk chocolate for 30 second increments until melted. Stir with a spoon between heating. Crush the caramel corn in a food processor until fine. Pour the chocolate mixture over the caramel corn. Stir with a spoon until incorporated. Chill in the refrigerator until set. Scoop with a number 70 ice cream scoop on to a plate lined with waxed paper. Reserve at room temperature until assembly.
• For the meringue: Combine the sugar and egg whites in a saucepan. Whisking constantly over low heat, bring the mixture to 110 degrees F. Pour the egg mixture into a standing mixer fitted with a whip attachment. Whip until it reaches room temperature; the mixture should be light, fluffy and shiny. Add the vanilla extract and salt. This recipe should be done just prior to assembly.
• To assemble: Push the caramel corn filling into the middle of each porter cupcake. Fill in the hole with the porter ganache. Chill until set.
• Fill a piping bag fitted with a star tip half full with the meringue. Pipe on top of the cupcake. Toast the meringue with a kitchen torch. Garnish with caramel corn.

CHOCOLATE CUPCAKES WITH VANILLA YOGURT CARAMEL FROSTING

Steps:

• Heat oven to 350°F. Place paper baking cup in each of 12 regular-size muffin cups.
• In small bowl, mix flour, baking powder, salt and cocoa; set aside. In medium microwavable bowl, microwave chocolate chips and oil uncovered on High 1 minute, stirring every 30 seconds, until melted and smooth. Stir in condensed milk and egg product. Add half of flour mixture at a time, stirring until incorporated. Divide batter evenly among muffin cups.
• Bake 20 to 25 minutes or until toothpick inserted in center comes out clean. Remove from pan to cooling rack; cool 10 minutes.
• Meanwhile, in small microwavable bowl, microwave caramel topping uncovered on High 30 seconds. Add yogurt, stirring well. Top each cupcake with 1 tablespoon mixture. Serve immediately.

CHOCOLATE SALTED CARAMEL CUPCAKES

Steps:

• Heat oven to 350°F.
• Prepare cake batter and bake as directed on package for 24 cupcakes, blending 1 pkg. dry pudding mix into batter before spooning into prepared muffin cups. Cool cupcakes in pans 10 min.; remove from pans to wire racks. Cool completely.
• Use small sharp knife to cut 1-1/4-inch-wide hole in top of each cupcake, being careful to not cut through to bottom of cake. Fill holes with caramel topping; cover with cupcake tops.
• Melt chocolate as directed on package; cool slightly. Beat remaining pudding mix, milk and powdered sugar in large bowl with whisk 2 min.; stir in COOL WHIP. Spread frosting onto cupcakes; drizzle with chocolate. Sprinkle with salt.

CHOCOLATE-MAYONNAISE CUPCAKES WITH CARAMEL-BUTTERSCOTCH BUTTERCREAM FROSTING RECIPE - (4.4/5)

Steps:

• Make the cake 1. Position a rack in the middle of the oven and preheat to 350°F (175°C). Line two standard 12-cup muffin tins with paper cupcake liners. 2. In a large bowl, sift together the flour, cocoa powder, baking soda, and salt. Set aside. 3. In another bowl, combine the sugar and eggs and beat with an electric mixer set at medium-high speed until light and fluffy, about 2 minutes. Beat in the mayonnaise and vanilla just until combined. Reduce the speed to medium and beat in half of the flour mixture just until combined. 4. Stop the mixer and scrape down the sides of the bowl. Add half of the boiling water and beat at very low speed, just until the batter is smooth, 5 to 10 seconds. Add the remaining flour mixture and beat just until combined, 5 to 10 seconds longer. Beat in the remaining water. The batter will be somewhat thin. 5. Divide the batter among the prepared cupcake cup liners, filling them about two-thirds full. Bake until a wooden skewer inserted into the center of a cupcake comes out clean, 18 to 22 minutes. Transfer the tin to wire racks and let cool completely. Make the caramel sauce 1. Combine the granulated sugar and water in a medium, heavy-bottomed saucepan over medium heat. Cook, gently swirling the pan occasionally, until the sugar dissolves and starts to change color. Increase the heat to high and boil until the syrup turns a deep amber color, 4 to 5 minutes. Watch carefully, as it can burn quickly. 2. Immediately remove the pan from the heat and stir in the cream with a wooden spoon. Return the pan to the stove, reduce the heat to medium-low, and cook, stirring constantly, until the caramel thickens, 3 to 5 minutes. Remove the sauce from the heat and let cool. Make the buttercream frosting 1. While the sauce is cooling, prepare the buttercream. Combine the eggs and brown sugar in the metal bowl of a standing mixer. (Alternatively, use a metal mixing bowl and a handheld electric mixer, but be prepared for a workout.) 2. Fill a large saute pan or frying pan with water and bring to a simmer over medium-high heat. 3. Place the mixing bowl in the simmering water and whisk the eggs and sugar constantly until the sugar is completely dissolved and the mixture is thick and fluffy and very hot, 3 to 4 minutes. Use an instant-read thermometer to check the temperature; it should be anywhere between 120°F and 140°F (49°C to 60°C). 4. Remove the bowl from the simmering water and, using the whisk attachment, beat the eggs at medium-high speed until they are tripled in volume and form soft peaks and the bottom of the bowl is completely cool to the touch, about 10 minutes. Beat in the vanilla and salt. 5. While the eggs are mixing, unwrap the individual sticks of butter and rewrap them loosely in plastic wrap. Pound the butter 5 or 6 times with a rolling pin, or until the butter is soft and malleable but still cool. 6. With the mixer speed still on medium-high, add the butter, approximately 2 tablespoons at a time, to the egg mixture, beating in each addition until it is incorporated. When all the butter has been incorporated, slowly dribble in the bourbon. Don't start to panic if the buttercream seems too liquid or looks curdled as you beat in the butter. It will magically emulsify into a smooth, creamy frosting by the time the last little bit of butter is mixed in. Have faith; it's worth it. 7. When the buttercream is smooth and glossy, turn off the mixer and, using a rubber spatula, fold in 1/2 cup of the cool caramel sauce. For a stronger flavor, fold in up to 1/2 cup more caramel sauce. 8. When the cupcakes are completely cool, frost them with the Caramel-Butterscotch Buttercream Frosting and serve.

CHOCOLATE SALTED CARAMEL CUPCAKES

Steps:

• 1. Make the Cupcakes: Preheat oven to 350 degrees F. Line standard-size muffin pans with paper liners.. 2. In a small bowl, whisk together the cocoa powder and hot water until smooth. In a separate medium bowl, whisk together the flour, baking soda, baking powder, and salt. 3. Combine the butter and sugar in a medium saucepan set over medium heat. Cook, stirring occasionally, until the mixture is smooth, and the butter is completely melted. Transfer the mixture to the bowl of an electric mixer and beat on medium-low speed until the mixture is cool, about 4 to 5 minutes. 4. Add the eggs one at a time, mixing well after each addition, and scraping down the sides of the bowl as needed. Add the vanilla and then the cocoa mixture, beating until smooth. 5. Reduce the mixer speed to low, and add the flour mixture in three additions, alternating with the sour cream, beginning and ending with the flour mixture. Mix each addition until just incorporated. 6. Divide the batter evenly between the prepared liners, filling each about two-thirds full. Bake until a toothpick inserted in the center comes out clean, 18 to 20 minutes, rotating the pans halfway through baking. Let cool in the pan for 10 minutes, then transfer to a wire rack to cool completely. 7. Make the Frosting: Beat together the butter and cream cheese on medium-high speed for 5 minutes (I like to use the whisk attachment for my KitchenAid stand mixer, but it's not necessary). Pour in the salted caramel and beat until combined. Reduce the speed to medium-low and slowly add the powdered sugar, a little at a time, until it has all been incorporated. Increase the speed to medium-high and beat for an additional two to three minutes, until light and fluffy. 8. To finish, pipe frosting onto the top of each cupcake (or use an offset spatula to spread the frosting), drizzle with some additional salted caramel sauce, and sprinkle with a pinch of fleur de sel. (Note: I used an Ateco #864 decorating tip to frost these)

CHOCOLATE CUPCAKES WITH CARAMEL FROSTING

Steps:

• Preheat oven to 350 degrees F (175 degrees C). Grease 15 muffin cups or line with paper baking cups.
• In a large bowl, stir together the white sugar, flour, cocoa, and baking soda. Make a well in the center, and pour in the water, grape jelly, mayonnaise, and 1 teaspoon of vanilla. Mix just until blended. Spoon the batter into the prepared cups, dividing evenly.
• Bake in the preheated oven until the tops spring back when lightly pressed, 20 to 25 minutes. Cool in the pan set over a wire rack. When cool, arrange the cupcakes on a serving platter.
• Make the frosting while the cupcakes cool. Combine the butter, half-and-half and brown sugar in a medium saucepan. Bring to a boil, stirring frequently. Remove from the heat and stir in the confectioners' sugar and vanilla. Set the pan over a bowl of ice water and whisk or beat with an electric mixer until fluffy. Frost cupcakes when they are completely cool.