In a large mixing bowl, combine the gluten-free flour, ¼ cup confectioners sugar, cinnamon, and salt. Mix well to combine.
Add the softened butter to the dry ingredients and use your fingers or a pastry cutter to incorporate it into the flour mixture until it resembles coarse crumbs.
Gradually pour in the marsala wine, stirring continuously until a dough forms. If the dough is too dry, you can add a little more wine, one tablespoon at a time, until it comes together.
Transfer the dough onto a lightly floured surface and knead it for a few minutes until smooth and elastic. Wrap the dough in plastic wrap and let it rest at room temperature for about 30 minutes.
While the dough is resting, prepare the filling. In a separate bowl, combine the ricotta cheese and ½ cup confectioners sugar. Mix until smooth and well combined. Then fold in the chocolate chips until evenly distributed. Place the filling in the refrigerator until ready to use.
After the dough has rested, roll it out on a floured surface to about 1/8 inch thickness. Use a round cutter or a glass to cut out circles from the dough.
Heat vegetable oil in a deep fryer or large pot to 350°F (175°C).
Wrap each dough circle around a cannoli tube, overlapping the edges slightly, and press to seal. You can use a little water to help seal the edges if necessary.
Carefully place the wrapped cannoli tubes into the hot oil, a few at a time, and fry until golden brown and crispy, about 3-4 minutes. Use tongs to remove the cannoli shells from the oil and transfer them to a paper towel-lined plate to drain and cool.
Once the shells have cooled completely, gently slide them off the cannoli tubes.
Just before serving, fill each cannoli shell with the prepared ricotta cheese filling. You can use a piping bag or spoon to fill the shells.
Dust the filled cannoli with additional confectioners sugar if desired, and serve immediately.