Make Dough: In a large mixing bowl, whisk together flour, sugar, salt, and cinnamon; add shortening and rub into flour with fingers until fully incorporated. Make a well in the center of the flour. Separate 1 egg into two small bowls, reserving the egg white for later use. Beat the other egg with the egg yolk and add to flour. Use a fork to slowly combine flour into egg mixture. When mixture resembles a thick paste and some of the flour has still not been incorporated, add wine and vinegar. Continue stirring until most of the flour has been incorporated. Invert onto a clean surface and knead for 5 minutes, until dough is supple. Wrap in plastic wrap and refrigerate 1 hour.

Make Filling: Unfold and layer cheesecloth inside a fine wire mesh strainer. Place ricotta in cheesecloth, wrapping entirely, and press the cheese until no more excess liquid drips when pressed. Transfer cheese to a large mixing bowl, sprinkle sugar and salt over cheese, and gently stir until just combined. (Note: It is very easy to overmix the cheese, turning the filling into a liquid, so only stir until the sugar is evenly distributed.) Sprinkle chopped chocolate on surface and gently fold once to combine. Refrigerate for at least 1 hour.

Assemble: Heat oil in a Dutch oven to 350°F. Cut dough into thirds, cover two of the thirds in plastic wrap, and roll the remaining dough to 1/16-inch thickness. Use the round cutter to cut 5 circles. Use a rolling pin to roll each circle into a 3- x 5-inch oval. Prick each oval all over with a fork. Collect dough scraps, and set aside to be rerolled later. Wrap oval around a cannoli tube so that the long sides overlap; use your finger to rub a small amount of reserved egg white in between where the dough surfaces touch and press to seal, being careful not to let any egg white touch the metal cannoli tube. Repeat with remaining ovals. Fry, constantly turning the tubes with a slotted spoon, until shells are bubbled and golden brown, about 4 minutes. Remove to a paper towel-lined plate to drain. When cool enough to handle, slip cannoli shells off of metal tubes and set aside.

Roll out another third of the dough and repeat process of cutting out circles, rolling into ovals, pricking with a fork, reserving scraps, wrapping cannoli tubes, and frying cannoli shells. Do this with remaining third of dough. Finally, collect all of the dough scraps into a ball and roll to cut out the final 3 circles of dough. Prepare like other cannoli shells.

Take chopped pistachios and place in a shallow bowl. Take ricotta filling out of refrigerator, transfer to piping bag, and fill each cannoli shell by inserting the piping bag into the tube and filling from the center to the edge of the cannoli shell on each side. Dip the end of each cannoli in the chopped pistachios. Dust with powdered sugar and serve.