These Oreo pop tarts have a cookies and cream filling that's surrounded by a flaky chocolate crust. They're also topped with a vanilla glaze and crushed Oreo pieces!
In a large bowl, whisk together the flour, cocoa powder, powdered sugar, and salt. Add the cubed butter and cut into the flour mixture using a pastry blender until it resembles crumbs.
Add 2 tablespoons of kefir milk and mix until combined. Add an additional 2 tablespoons at a time until the dough starts to form large clumps and is both slightly sticky and dry. I used 7 tablespoons (be careful not to add more than you need).
Pour onto a work surface that has been lightly dusted with cocoa powder and press the dough together until a ball forms. Divide the dough in half, flatten into a disk shape, and wrap it in plastic wrap. Chill in the refrigerator for 1 hour.
Oreo Filling
In the bowl of an electric stand mixer using the paddle attachment, beat together the cream cheese, powdered sugar, vanilla extract, and milk on high speed until combined and creamy. You may need to scrape the sides of the bowl a few times. Then fold in the crushed Oreos.
Assemble
Remove one of the dough disks from the refrigerator and place it on a surface that has been lightly dusted with cocoa powder again. Use a rolling pin to roll out the dough into a rectangle shape.
Use a pizza cutter and a ruler to cut the dough into 2½"x3½" inch rectangles. Repeat with the other pie dough. You'll need a total of 16 rectangles.
On a baking sheet lined with a silicone baking mat, place one rectangle on and lightly brush it with the egg wash. Add about ½ tablespoon of the Oreo filling directly to the center of the dough and place another rectangle on top. Use a fork to crimp down all sides of the dough until fully sealed.
Repeat the step above until all 8 of your pop tarts have been formed. Place the baking sheet into the freezer while the oven preheats.
Preheat the oven to 400 degrees. Once heated, use a toothpick or a knife to gently poke holes on top of the dough and lightly brush with the egg wash. Place the whole pan into the oven and bake for 15-20 minutes, or until the edges appear set.
Cool on the baking sheet for 10 minutes before transferring them over to a wire rack to finish cooling.
Vanilla Icing
In a small bowl, mix together the powdered sugar, kefir milk, and vanilla extract until combined. If the glaze is too thick, add ½ teaspoon of the milk. If too thin, add ½ teaspoon of powdered sugar.
Spoon the icing over the cooled pop tarts and top with the Oreo crumbs and pieces. Keep any leftovers in an airtight container in the refrigerator for up to 4 days.
Notes
Pie Dough: Once you make the dough, cover it in plastic wrap and chill in the refrigerator for 1 hour before rolling it out. You can also make the dough the night before and let it sit at room temperature for 10 minutes before using.Pop Tart Size: Use a pizza cutter and a ruler to cut the dough into a 2½"x3½" inch rectangle. You'll need a total of 16 rectangles. If you have a rectangle cookie cutter, that would work too. This recipe will make 8 pop tarts.Icing: Wait until the pastries are completely cooled before drizzling on the icing.