Add flour, dark brown sugar, cocoa powder, cinnamon, and salt to food processor and pulse until blended. Add melted butter and egg yolks and pulse until blended. Slowly pour in Sherry Cooking Wine while pulsing food processor; continue to pulse until dough begins to come together. Shape dough into ball, and flatten into disk. Chill 30 minutes in refrigerator.
Roll dough on a lightly floured surface into 14-inch circle, about ¼-inch thick. Carefully move dough to tart pan and press dough evenly into every corner of tart shell. Cut off excess dough with paring knife. Place tart shell into refrigerator for 15 minutes to chill are rest.
Move oven rack to middle position and preheat oven to 350 degrees F while tart shell chills. Place tart pan on cookie sheet. Line tart with foil and place 1 pound of dried beans or pie weights on top of foil. Bake 30 minutes, then remove foil and weights, and return tart to oven to bake 8 more minutes. Place tart on oven rack to cool completely, about 2 hours.
MAKE CANNOLI FILLING:
In bowl of stand mixer fitted with whisk attachment, whip cream until stiff peaks form. Place cream into small bowl and set aside.
In the same mixing bowl, add ricotta cheese, powdered sugar, orange zest or extract, vanilla, and cinnamon. Mix on medium speed until well combined, about 1 minute. Fold in whipped cream and chocolate chips.
ASSEMBLE CANNOLI TART:
Pour filling into cooled tart shell, and use offset spatula to smooth into even layer. Chill tart 2 hours.
MAKE CHOCOLATE TOPPING AND FINISH:
In small sauce pan, heat cream over medium heat until just starting to bubble, about 2-3 minutes. Pour cream over chopped bittersweet chocolate and let it sit for 5 minutes, and then stir until chocolate is melted.
Pour chocolate over cannoli tart and carefully smooth into even layer. Sprinkle with mini chocolate chips. Place tart in fridge so ganache can set, about 60 minutes. Slice and serve!