In a medium bowl, beat the softened cream cheese with a hand mixer until smooth and fluffy. Add the 1/4 cup granulated sugar, powdered sugar, vanilla, and a pinch of salt. Beat again until creamy with no lumps.
8 ounces cream cheese, 1/4 cup granulated sugar, 2 tablespoons powdered sugar, 1/2 teaspoon vanilla extract, 1 pinch salt
Scoop small teaspoons of the cream cheese mixture onto a parchment-lined plate or tray, aiming for about 18–20 small mounds. Freeze for 20–30 minutes, until firm enough to handle.
In a large bowl, whisk together the flour, cocoa powder, baking soda, and salt. Set aside.
2 1/2 cups all-purpose flour, 3 tablespoons unsweetened cocoa powder, 1 teaspoon baking soda, 1/2 teaspoon fine sea salt
In another large mixing bowl or the bowl of a stand mixer fitted with the paddle attachment, beat the softened butter, oil, 1 cup granulated sugar, and brown sugar until light and fluffy, about 2–3 minutes. Scrape down the bowl once for even mixing.
1/2 cup unsalted butter, 1/2 cup neutral oil, 1 cup granulated sugar, 1/2 cup light brown sugar
Beat in the eggs one at a time, mixing well after each addition. Add the vanilla, then the red food coloring and vinegar. Start with the lower amount of coloring and add more if you want a deeper red. The mixture will resemble thick cake batter.
2 large eggs, 2 teaspoons pure vanilla extract, 1-1 1/2 tablespoons red liquid food coloring, 2 teaspoons distilled white vinegar
On low speed, gradually add the flour mixture to the wet ingredients, mixing just until no dry streaks remain. If using chocolate chips, gently fold them in. The dough will be soft and slightly sticky.
2 1/2 cups all-purpose flour, 3 tablespoons unsweetened cocoa powder, 1 teaspoon baking soda, 1/2 teaspoon fine sea salt, 1/2 cup white chocolate chips or mini chocolate chips
Cover the bowl and refrigerate the dough for at least 45–60 minutes, until noticeably firmer. This makes stuffing easier and helps the cookies bake up thick and soft.
Preheat the oven to 350°F (175°C). Line two baking sheets with parchment paper or silicone baking mats. If you plan to roll the cookies in sugar, pour the extra 1/4 cup granulated sugar into a small bowl.
1/4 cup granulated sugar
Scoop about 2 tablespoons of cookie dough and flatten it slightly in your hand. Place one frozen cream cheese mound in the center. Gently wrap the dough around the filling, sealing all seams so no cream cheese is exposed, and roll into a smooth ball. If desired, roll the ball lightly in granulated sugar. Place on the baking sheet, spacing cookies about 2 inches apart. Repeat, working in batches so the filling stays cold.
Bake each tray for 11–13 minutes, until the cookies are set around the edges but still soft and slightly puffy in the center. They should look just slightly underbaked in the middle. Let the cookies cool on the baking sheet for 10 minutes, then transfer to a wire rack to cool completely. The centers will stay soft and creamy.
If any cookies bake a little lopsided, immediately after removing from the oven you can gently nudge the edges into a neater circle with a round cookie cutter or the back of a spoon for a bakery-style look.