Preheat your oven to 350°F. Line two 12-cup standard muffin tins with paper liners. This step is crucial as it prepares your baking environment for the delicious cupcakes to come.
In the bowl of a stand mixer fitted with the paddle attachment, or in a large bowl using an electric mixer, combine 1 cup unsalted butter and 1 ½ cups sugar. Cream on medium speed for about 5 minutes until the mixture is light and fluffy. The color should turn pale and the texture smooth.
In a medium bowl, sift together 2 ¾ cups cake flour and 1 tablespoon baking powder. This step is important as it helps prevent clumps in your batter and ensures even distribution of the leavening agent.
Add the eggs one at a time to the butter mixture, making sure to mix well between each addition. Scrape down the sides of the bowl with a rubber spatula and mix for an additional 30 seconds. This helps incorporate all the ingredients properly.
Next, add in half of the flour mixture, followed by all of the 1 cup whole milk and 2 ½ teaspoons pure vanilla extract. Finally, add the rest of the flour mixture. Scrape the sides again and mix for another 30 seconds until the batter is smooth.
Now, fold in ⅓ cup finely ground graham cracker crumbs with a rubber spatula. This adds a delightful texture to your cupcakes.
Using a large cookie scoop or a ¼-cup measure, divide the batter evenly between the prepared muffin pans. The batter should fill each liner about two-thirds full.
Bake in your preheated oven for 18 to 22 minutes. They are done when a toothpick inserted in the center comes out clean. Watch for a light golden color on top!
Once baked, place the pans on cooling racks and let the cupcakes cool completely. This step is essential before frosting!
In a stand mixer, cream together 8 ounces cream cheese and 4 tablespoons unsalted butter until well combined and fluffy, about 5 minutes. The mixture should be smooth and creamy.
With the mixer on low, gradually add in 1 pound confectioners’ sugar until thoroughly incorporated. Then, add in 2 teaspoons pure vanilla extract and mix to combine. Turn the mixer to medium speed and let it run for about 5 more minutes until the frosting is light and fluffy.
Now comes the fun part! Pipe or spread the frosting onto the cooled cupcakes. I love to use a star tip for a beautiful swirl!
Finally, sprinkle the frosted cupcakes with ½ cup coarsely chopped graham cracker crumbs and top them with 1 can cherry pie filling. This adds a beautiful finish and a burst of juicy flavor.