Crush the chocolate cookies in a large bowl until they resemble coarse crumbs, using a rolling pin or food processor.

In another bowl, whip the heavy cream until it forms soft peaks. Gradually add the powdered sugar and vanilla extract while continuing to whip until fluffy.

Gently fold the crushed cookies into the whipped cream mixture to create the filling.

Lay out a large piece of parchment paper and spoon the cookie and cream mixture onto one end. Roll it up into a tight cylinder.

Chill the roll in the refrigerator for about 1 hour to set.

Slice the chilled roll into 1-inch pieces, drizzle with chocolate syrup, and sprinkle with crushed cookies before serving.