Red Velvet Hamantaschen with Cream Cheese Filling

Place 1 1/3 cups granulated sugar, 4 large eggs, 2/3 cup canola oil, 1 1/2 teaspoons vanilla extract, and 1/4 teaspoon kosher salt in the bowl of a stand mixer (or large bowl if using an electric hand mixer). Beat on high speed with the paddle attachment until combined, about 30 seconds.

Add 2 teaspoons red gel food coloring and beat on high speed until combined; beat in up to 1/2 teaspoon more food coloring as needed until the dough is dark red. Add 4 cups all-purpose flour and 4 teaspoons unsweetened dark cocoa powder. Beat on medium-low speed until the dough comes together, scraping down the beater and bowl about halfway through, about 2 minutes total.

Cover the bowl and refrigerate for at least 1 hour or up to 1 day to firm up. Meanwhile, make the filling.

Place 12 ounces cream cheese, 1/3 cup granulated sugar, 1 large egg yolk, 1 teaspoon all-purpose flour, and 1/2 teaspoon vanilla extract in a clean, dry stand mixer bowl (or medium bowl if using an electric hand mixer). Beat with the paddle attachment, starting on low speed and gradually moving up to high speed, until creamy, about 20 seconds. Cover and refrigerate until you are ready to shape the hamantaschen, up to 1 day in advance.

Arrange 2 racks to divide the oven into thirds and heat the oven to 350ºF. Line 2 to 3 rimmed baking sheets (however many you have) with parchment paper or silicone baking mats.

Divide the dough in 3 pieces (about 13 ounces each). Sprinkle a sheet of parchment paper with all-purpose flour. Place a piece of dough in the center and sprinkle with more all-purpose flour, then top with a second sheet of parchment paper. Use a rolling pin to roll out the dough until about 1/4-inch thick. Every few rolls, peel back the top parchment and sprinkle a little more flour on the dough. Once or twice during the rolling, turn the entire packet over, lift up the bottom parchment, sprinkle a little flour on the dough, recover, and then flip over to continue rolling. This makes it easier to roll as well as prevents sticking.

Uncover the dough. Cut out as many rounds as you can with a 3-inch round cutter, making sure to twist to cut perfect rounds. Remove the excess dough from around the rounds.

Fill the hamantaschen one at a time: Place 1 level teaspoon of the filling (resist the urge to add more!) in the center of a round. Lift the round up to make sure it is not sticking, then return it to the parchment. Fold the sides in toward the middle in 3 parts to form a triangle, leaving an opening in the center no larger than 3/4-inch. Pinch the three sides together very tightly.

Place on a baking sheet. Repeat filling and shaping the remaining dough rounds, spacing them about 1-inch apart on the baking sheets, 18 to 20 per sheet. Repeat rolling out and filling the remaining 2 portions of dough.

Gather the remaining dough scraps together and form a ball, then sprinkle with a little flour. Reroll between the parchment, cut, fill, and shape until you run out of filling or dough.

Before you bake the cookies, pinch all of the corners of the cookies for a second time.

Bake 2 sheets at a time: Bake for 7 minutes. Rotate the baking sheets between racks and from front to back. Bake until the cookies are set and no longer stick to the pan (they will not look browned due to the red color), 5 to 6 minutes more. Do not bake until the cookies are fully firm, as they will be too dry.

Slide the parchment or mat with the cookies on them onto wire racks and let cool completely.

Place 1 cup powdered sugar, 2 teaspoons hot water, and 1/4 teaspoon vanilla extract in a medium bowl and whisk until smooth. Whisk in more hot water 1/4 to 1/2 teaspoon at a time until you have a very thick glaze that drips in a steady stream when the whisk is lifted out of the glaze. If the glaze is too thin, whisk in a little more powdered sugar.

Drizzle lines of the glaze with a whisk onto one corner of the cookies. Let sit until the glaze is set, about 10 minutes.