Preheat the oven to 350 degrees F. With your hands, shape the roll of cookie dough so it forms a point all along the top and remains rounded at bottom. If the dough is too soft to cut, wrap in plastic wrap, and place in the freezer for 15 minutes.
With a thin, sharp knife, cut the dough into 24 slices (about 3/8-inch thick). Place 2 inches apart on an ungreased cookie sheet. Place a cut pretzel piece at the top of each cookie at a slight angle. Bake until cookies are set, 9 to 11 minutes. Cool 1 minute; remove from the cookie sheet to a cooling rack. Cool completely.
In a small microwavable bowl, microwave the chocolate chips and oil uncovered on High for 1 to 2 minutes, stirring every 30 seconds, until smooth. Using a frosting spatula or knife, spread the chocolate on the top portion of each cookie to look like acorn shell. Place on waxed paper. Immediately sprinkle the crushed pretzels over the chocolate. Let the chocolate set before serving.
