In a mixing bowl, combine flour, sugar, cinnamon, and salt. Cut in butter until mixture resembles coarse crumbs.
Add the beaten egg and wine, mixing until dough forms. Knead until smooth, about 2 minutes. Wrap in plastic and let rest for 30 minutes.
Roll dough out to ⅛ inch thickness. Cut into 4-inch circles. Wrap circles around cannoli molds, sealing edges with a bit of beaten egg.
Heat oil in a frying pan to 350°F (175°C). Fry shells until golden brown, about 2 minutes. Remove and drain on paper towels. Let cool before removing molds.
For the filling, mix ricotta, powdered sugar, and vanilla extract until smooth. Fold in chocolate chips.
Fill cooled shells with ricotta mixture just before serving. Dust with powdered sugar if desired.