In a food processor, pulse the flour, salt, confectioners' sugar, and cinnamon 2 or 3 times. Add the butter and pulse until it resembles coarse crumbs. With the machine running, pour the wine in all at once and process 4 to 5 seconds. Turn the mixture out onto a sheet of plastic wrap, gently pressing it all into one ball. Wrap tightly and refrigerate for 30 minutes.
Roll the rested dough out between 2 sheets of plastic to 1/4-inch thickness.
Preheat the oven to 400 degrees F.
Butter the bottom and sides of a 10-inch tart pan and line the pan with the dough. Chill it well and bake in the oven 12 minutes. Set aside to cool. Reduce heat to 375 degrees F.
In a saucepan over medium heat, bring the cream to a simmer. Remove from the flame, add the chocolate, and stir to melt. Let the mixture cool for 20 minutes.
Using a whisk, beat in the cocoa and eggs. Add the aniseeds and 1 tablespoon liqueur, whisking again. Pour the mixture into the tart shell and bake at 375 degrees F for 15 minutes, just until the chocolate forms a shiny skin and is slightly firm but unset at the center. Cool for 15 minutes, then remove the tart from the pan to cool completely.
Beat the confectioners' sugar with the milk and remaining 2 teaspoons liqueur to a thin and pourable consistency. Add a few drops of milk, if needed, to keep the glaze from getting too thick. Drizzle the cooled tart with the glaze in a zig-zag pattern and allow the glaze to harden. Serve with anise liqueur.