1. Prepare Oven and Pan; Make Cake Batter:

• Preheat your oven to 350°F (175°C).
• Line a 10×15-inch jelly roll pan (a rimmed baking sheet) completely with parchment paper, allowing a slight overhang on the shorter sides if possible, to make lifting the cake easier later. Lightly grease the parchment paper or spray it with non-stick cooking spray.
• In a large mixing bowl, prepare the chocolate cake mix according to the specific instructions on its package. This usually involves combining the dry cake mix with the number of eggs, amount of oil, and amount of water listed on your box, plus the 1 teaspoon of vanilla extract for the cake. Mix with an electric mixer on low speed to combine, then on medium speed for the time specified on the box (usually about 2 minutes), until the batter is smooth. Do not overmix.

2. Bake the Thin Chocolate Cake Layer:

• Pour the prepared chocolate cake batter into the parchment-lined jelly roll pan.
• Using an offset spatula or the back of a spoon, gently spread the batter into an even layer, ensuring it reaches all the corners of the pan. The layer will be quite thin.
• Bake in the preheated oven for 12-15 minutes. The cake is done when it springs back lightly when gently touched in the center, and a toothpick inserted into the center comes out clean. Because it’s a thin layer, it bakes very quickly – be sure to watch it carefully to avoid overbaking, which can make it dry and prone to cracking.

3. Roll the Warm Cake in a Towel and Let Cool:

• While the cake is baking, prepare your rolling surface. Lay a clean, lint-free kitchen towel flat on your countertop or work surface. Dust the towel generously and evenly with the ¼ cup of powdered sugar. Make sure the sugared area is larger than the cake.
• As soon as the cake comes out of the oven, immediately and carefully invert the hot jelly roll pan onto the prepared sugar-dusted towel.
• Gently and slowly peel off the parchment paper from the bottom (now top) of the cake.
• While the cake is still very warm and pliable (this is crucial!), starting from one of the short sides of the cake, carefully and snugly roll the cake up with the towel inside the roll. The towel prevents the cake from sticking to itself as it cools and helps it “learn” the rolled shape.
• Place the rolled-up cake (still wrapped in the towel) seam-side down on a wire cooling rack. Let it cool completely in this rolled position. This will take at least 1 hour, or possibly longer, until it’s no longer warm to the touch.

4. Make the Oreo Cream Cheese Filling:

• While the cake roll is cooling, you can prepare the delicious filling. Ensure your cream cheese and butter are properly softened to room temperature for the smoothest result.
• In a medium or large mixing bowl, using an electric mixer, beat the softened cream cheese and softened butter together on medium-high speed until the mixture is completely smooth, creamy, and well combined. Scrape down the sides of the bowl as needed.
• Reduce the mixer speed to low. Gradually add the sifted powdered sugar and the 1 teaspoon of vanilla extract (for the filling). Mix until all the powdered sugar is fully incorporated and the filling is smooth and fluffy.
• Using a rubber spatula, gently fold in the ½ cup of crushed Oreo cookies, distributing them evenly throughout the cream cheese mixture. Try to leave some texture from the cookie pieces.

5. Assemble the Oreo Roll Cake:

• Once the rolled cake is completely cool to the touch, gently and carefully unroll it flat onto the towel (which will now have absorbed some powdered sugar).
• Spread the prepared Oreo cream cheese filling evenly over the entire surface of the unrolled cake, leaving about a ½-inch border along the edges. This helps prevent too much filling from squeezing out when you re-roll it.
• Carefully re-roll the cake, without the towel this time, starting from the same short side you started rolling from initially. Roll it up snugly but gently, trying to keep the filling intact and ensuring the cake roll is tight.

6. Chill the Roll Cake:

• Carefully transfer the assembled Oreo Roll Cake, seam-side down, to a long serving platter or a baking sheet lined with fresh parchment paper or plastic wrap.
• Wrap the rolled cake securely in plastic wrap.
• Refrigerate for at least 1 hour (or up to 4 hours, or even overnight if making ahead) to allow the filling to firm up and the cake to set completely. This chilling step is important for making slicing much neater.

7. Decorate:

• Just before you plan to serve, prepare the white chocolate drizzle and other garnishes.
• Place the ¼ cup of white chocolate chips or chopped white chocolate baking bar into a small microwave-safe bowl. Microwave in short 15-20 second bursts, stirring well after each interval, until the white chocolate is melted and smooth. Be careful not to overheat white chocolate, as it can seize.
• Unwrap the chilled Oreo Roll Cake. Drizzle the melted white chocolate decoratively over the top of the roll using a spoon or by transferring the melted chocolate to a small piping bag or Ziploc bag with a tiny corner snipped off.
• Decorate the cake roll with the whole Oreo cookies (you can press them gently onto the roll or arrange them alongside slices) and sprinkle with the extra crushed Oreo cookies for a final garnish.

8. Slice and Serve:

• Using a sharp serrated knife, slice the decorated cake roll into 1-inch or 1.5-inch thick portions. For the cleanest slices, you can wipe the knife blade clean with a warm, damp paper towel between each cut.
• Serve immediately and watch everyone enjoy this decadent Oreo Cream Roll Cake!