How to Make Grandma’s Classic Filled Roll Cookies

In a large mixing bowl, combine the flour, sugar, and salt. Add the cold, cubed butter and cut it into the flour mixture using a pastry blender or your fingertips until it resembles coarse crumbs. If using a food processor, pulse until the butter is pea-sized. In a separate small bowl, whisk together the sour cream, egg yolk, and vanilla extract. Add the wet ingredients to the dry ingredients and mix until just combined, forming a shaggy dough. Do not overmix. Form the dough into a disc, wrap it tightly in plastic wrap, and refrigerate for at least 2 hours, or preferably overnight. Chilling is crucial for a flaky texture.

Preheat your oven to 375°F (190°C). Line baking sheets with parchment paper. On a lightly floured surface, divide the chilled dough into two equal portions. Work with one portion at a time, keeping the other refrigerated. Roll out the dough into a thin rectangle, approximately 1/8 inch thick. The dimensions will depend on your desired cookie size. Evenly spread your chosen filling over the entire surface of the rolled-out dough, leaving a small border along one long edge if you prefer.

Starting from a long edge, tightly roll the dough into a log. Once rolled, gently pinch the seam to seal it. Using a sharp knife or pastry wheel, cut the log into 1-inch thick slices. Carefully transfer the individual cookies to the prepared baking sheets, leaving a little space between each. Repeat with the remaining dough and filling.

Bake the roll cookies in the preheated oven for 15-20 minutes, or until the edges are lightly golden brown. Baking times may vary depending on your oven and cookie thickness. Once baked, remove the cookies from the oven and let them cool on the baking sheets for a few minutes before transferring them to a wire rack to cool completely. Once cool, dust generously with powdered sugar before serving.