Preheat your oven to 350Ā°F (175Ā°C). Line a 12-cup muffin tin with paper liners and set aside.
In a large mixing bowl, whisk together the flour, sugar, cocoa powder, baking soda, and salt until evenly combined with no streaks.
In a separate bowl, whisk together the oil, buttermilk, eggs, red food coloring, and vanilla extract until smooth and fully blended.
Pour the wet ingredients into the dry ingredients and stir gently with a spatula until just combinedāa few small lumps are fine. Gently fold in the vinegar with 3-4 strokes; don't overmix.
Divide the batter evenly among the lined cups, filling each about two-thirds full. Tap the pan firmly on the counter twice to release air bubbles.
Bake for 18-20 minutes, until a toothpick inserted in the center comes out with just a few moist crumbs. The tops should spring back when lightly pressed.
Remove from the oven and let cool in the pan for 5 minutes, then transfer cupcakes to a wire rack to cool completely before frostingāabout 45 minutes.
For the frosting, beat the softened cream cheese and butter together on medium-low speed for 2 minutes until creamy and smooth with no lumps.
Gradually add the sifted powdered sugar one cup at a time, beating on low speed after each addition. Add the vanilla extract and beat for 1 more minute until fluffy but not airy.
Frost the cooled cupcakes with a knife, offset spatula, or pipe decorative swirls using a large star tip. Refrigerate for 15 minutes to set before serving.
