Adjust the oven racks to the upper- and lower-middle positions and preheat the oven to 350 degrees Fahrenheit. Line two baking sheets with Gefen Parchment Paper and set aside.

Mix the sugar and cinnamon together.

Divide the dough into quarters. Lightly flour a work surface and dust the top of a piece of dough with flour. Roll into a 10-inch circle, flipping halfway through rolling. (You want it to stick a little bit for easier rolling, as the brief kneading of the dough causes it to spring back when you roll it out.) Brush the top with oil and spread a quarter cup of the cinnamon-sugar mixture over it leaving a half-inch border. Sprinkle two ounces (or a quarter) of the chocolate over the sugar.

Cut the dough into eight even triangles (like a pizza) and roll each piece up, starting from the outer edge, using a bench scraper to loosen the dough if needed. Place rugelach seam-side down on the prepared baking sheet. Repeat with remaining pieces of dough.

Bake rugelach for 12 minutes, rotating and switching pans halfway through baking, until they are pale golden brown.