In a large bowl, whisk together flour, sugar, and salt. Create a well in the center and add olive oil, beaten egg, and wine. Mix until a shaggy dough forms.
Turn dough onto a floured surface and knead for 8-10 minutes until smooth and elastic. The dough should be firm but not dry. Wrap in plastic and rest for 30 minutes at room temperature.
In a large bowl, gently fold together the drained ricotta, powdered sugar, vanilla extract, lemon zest, and cinnamon if using. Don't overmix - maintain some texture.
Fold in chocolate chips gently. Cover and refrigerate for at least 2 hours or overnight. Transfer to a piping bag with a large round tip before serving.
Divide dough into 12 pieces. Roll each piece very thin on a floured surface, about 4 inches in diameter. Wrap each circle around a cannoli tube, sealing the overlap with a dab of water.
Heat oil to 375°F in a heavy pot or deep fryer. Fry cannoli shells 2-3 at a time for 2-3 minutes until golden brown and bubbling. Remove carefully and cool completely before removing from tubes.
Just before serving, pipe filling into shells from both ends. Dust with powdered sugar and serve immediately.
Notes
Storage tip: Keep shells and filling separate until ready to serve. Shells stay crispy for 3 days in airtight container. Never store filled cannoli as shells will become soggy.