Place milk and yeast in the bowl of a stand mixer and lightly whisk. Allow to stand until frothy and yeasty smelling, about 3 minutes.
Place flour, sugar, spices and salt in a large bowl and whisk to combine. Slowly mix flour mixture, using the hook attachment, into yeast mixture.
Add yolks and mix until a rough dough forms, about 1-3 minutes. Add the butter, increase the speed, and mix until the dough is smooth, shiny, and elastic, about 5 minutes. It should be tacky, sticking to the bottom of the bowl but not to the sides or dough hook.
Coat a large bowl with oil. Form the dough into a ball and place in the bowl, roll dough in bowl to lightly coat it in oil. Cover with a damp tea towel and let rise in a warm place (or cold oven) until doubled in size, about 1-1 1/2 hours.
Lightly flour a large plate or sheet pan. Set aside. Punch down the dough, transfer to a lightly floured work surface and roll until about 1/4 inch thick. Using a 2-inch round cutter, cut out dough rounds and place on the floured pan 1/2 inch apart. Roll the scraps gently into a ball and roll out again, cut into rounds.
Cover loosely with a damp towel. Let rise in a warm place/cold oven until doubled in thickness, about 30-45 minutes.
Meanwhile, prepare the ganache. Place the chocolate in a small bowl. Heat the heavy cream over medium low heat until it just starts to boil. Pour the heated cream over chocolate and let stand for 5 minutes. Gently stir chocolate and cream together. Stir in the molasses. Cover with plastic wrap making sure it is touching the surface of the ganache. Let stand until ready to use.
Get ready to fry. Pour about a quart and a half of canola oil in a large, heavy-bottomed pot and heat until the temperature reaches 350℉. Meanwhile, line a second baking sheet with paper towels and place a wire rack over the paper towels. Set aside.
Use a large, flat spatula to lift the doughnuts into the oil, taking care not to over crowd the pan. Cook for 1-2 minutes on each side.
Drain on wire rack over paper towel-lined baking sheet. Repeat for remaining dough.
Make the glaze. Mix together powdered sugar, spices and milk in a bowl. Stir well. If too thick add more milk, if too thin add more powdered sugar.
Fill the donuts using a piping bag or plastic squeeze bottle. Cut a hole into the side of the donut with a small knife and pipe in ganache, not too much, a little goes a long way.
Dip each doughnut into the glaze and set aside.
Decorate with a Hanukkah shaped gingerbread cookie and enjoy!