To make the doughnuts, in a medium bowl, combine 1 tablespoon of the yeast with 3/4 cup of the warm milk and stir to dissolve the yeast. Add 3/4 cup of the flour and stir to create a smooth paste. Cover the bowl with plastic wrap and let the flour mixture rest in a warm place for 30 minutes. Once 30 minutes have passed, in the bowl of a stand mixer fitted with the paddle attachment, combine the remaining 1 tablespoon plus 1 teaspoon of yeast with the remaining 1/4 cup milk. Now add in the rested flour mixture along with the tsp of vanilla and the 3 large egg yolks. Mix on low until the ingredients are incorporated and the dough is smooth, about 30 seconds. Turn off the mixer and add 1 cup of flour, along with the 2 Tbsp. sugar and the 1/2 tsp. salt. Mix on medium until the dough starts to come together, about 30 seconds. Add the butter and mix on medium until it's incorporated, about another 30 seconds. Remove the paddle attachment from the mixer, and switch to the dough hook. Start adding the remaining flour, 1/4 cup at a time, and knead the dough on medium until it completely pulls away from the side of the bowl and is smooth and not too sticky, about 1 minute. The dough will be very soft and moist but not so sticky that you can't roll it out. Cover the bowl with plastic wrap and let the dough rest in a warm place for 1 hour. After one hour, gently press down on the dough to remove any gas bubbles. At this point you can either roll the dough out or chill the dough, covered, for up to 24 hours.

During this time, make the cream. Place the milk and vanilla bean in medium sauce pot set of over medium-low heat. Bring the milk to a low simmer and allow the vanilla to infuse the milk. In a mixing bowl whisk together the egg yolks and sugar, whisk in the flour until smooth. Once the milk is hot, add about 1/3 cup of the hot milk to the egg mixture and quickly whisk to combine. Add the egg mixture to the rest of the milk, whisking consistently to prevent the eggs from curdling. Continue to cook the mixture until very thick and creamy, about five minute. Remove from the heat and strain the cream through a fine mesh strainer, discard the vanilla bean. Cover the cream with plastic wrap and place in the fridge to cool.

Now take the heavy whipping cream and whisk it until stiff peaks form, about 5 minutes on high speed. Remove the cooled vanilla cream from the fridge and fold it into the whipped cream. Refrigerate until until ready to use.

When ready to roll out the dough, line 2 baking sheets with parchment. Lightly flour a work surface and roll out the dough to a 1/2-inch thickness. Cut the dough in 15-20 squares and then roll each square into a ball. Arrange the doughnuts on the prepared baking sheet, leaving at least 1 inch between doughnuts. Cover the doughnuts loosely with plastic wrap and let them proof in a warm place, about 20-30 minutes.

In a heavy-bottomed large pot or deep fryer, heat at least 2 inches of oil until a deep-fry thermometer registers 350 degrees F. Working in batches, use a slotted metal spoon or spatula to carefully place the doughnuts in the hot oil. Fry, flipping once, until light golden brown, 1 to 2 minutes per side. When done, transfer to a the wire rack. Make sure to return the oil to 350 degrees F. between batches. Let the doughnuts cool slightly (about 2-5 minutes) before filling. Then cover in sugar.

To make the hot chocolate sauce, warm the milk and heavy cream over medium-low heat until bubbles start to show and it begins to lightly and slowly boil. Add the chocolate and whisk until smooth and fully incorporated. Remove from the heat and stir in the Cabernet wine and butter. Transfer to a fondue pot heated over a low flame. Or use a cast iron sauce pot and keep the pot over the lowest flame possible. If the sauce begins to feel a little stiff, add a tablespoon of heavy cream and stir.

Now pierce the base of each doughnut with a piping tube and pipe a little cream filling into each doughnut. Serve warm with the warmed hot chocolate sauce for dipping. Grab a cold milk. Enjoy!