Preheat the oven to 350°F. Line the cupcake pan with 12 paper liners.
In a medium bowl, whisk together the flour, sugar, granulated sugar, cocoa powder, baking soda, and salt.
In a large bowl, whisk together the eggs, buttermilk, oil, vanilla, and red food coloring.
Add about half of the dry ingredients into the wet mixture. Mix until somewhat incorporated then add in the rest of the dry ingredients. Mix until almost fully incorporated, then mix in the vinegar until just combined.
Divide the batter evenly among the 12 cupcake liners, filling them about ⅔ full.
Bake for 18-22 minutes, until a toothpick inserted in the center comes back clean or with a few moist crumbs. Leave cupcakes in the pan for 5 minutes then transfer them to a wire rack.
In a medium microwave safe bowl, heat up the raspberry jam for 20-30 seconds just until melted once stirred. Add a little red food coloring until desired color is achieved.
Once the cupcakes have cooled. With the wide end of a frosting tip, press down and spin on the top of each cupcake until you can’t push down any further. Just don’t go through the bottom of the cupcake. If you don’t get enough cake out, use a knife to scoop out more. Save the scooped out pieces. You can also try using a melon baller or a knife to remove the cake.
Once the jam has cooled a bit, add about 2 teaspoons of the jam to the well of each cupcake. Replace the scooped out pieces over the top.
Add softened cream cheese, butter, powdered sugar, vanilla extract, and salt to the bowl of a stand mixer fitted with a paddle attachment. Beat until creamy. If the frosting is too soft, you can put it in the fridge for 10-15 minutes to firm it back up, max 20 minutes.
Using either a #1A or #2A piping tip, frost each cupcake.
Using a toothpick or skewer, make two small holes in the frosting.. Add drips of the jam into the holes then down the sides a little to form the bite marks (I use a 1 ml syringe).