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1
Combine the milk, cream, sugar, vanilla bean and seeds in a medium saucepan, bring to a simmer and cook until the sugar is completely dissolved, about 1 minute.
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2
Remove the pan from the heat, add the chocolate and let sit for 30 seconds.
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3
Whisk the mixture until smooth.
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4
Keep warm.
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5
Put the oil into a large saucepan and heat over medium heat until a deep fry thermometer registers 365 degrees F. Place several layers of paper towels on a baking sheet and set aside.
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6
Combine the water, butter, 1/4 cup sugar, and salt in a medium saucepan over high heat.
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7
Bring to a boil and cook until the butter is completely melted and the sugar is dissolved.
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8
Add the flour, 1/4 teaspoon cinnamon and 1/4 teaspoon anise seeds and quickly beat with a wooden spoon until a ball is formed and the mixture becomes dry, about 2 minutes.
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9
Transfer the mixture to the bowl of a stand mixer fitted with the paddle attachment and beat for one minute to allow some of the steam to escape the mixture and to cool slightly before adding the eggs.
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10
Add the eggs, one a time, beating every time until each is incorporated.
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11
Add the vanilla extract and beat for 20 seconds longer.
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12
Scrape the mixture into a pastry bag fitted with a large star tip.
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13
Combine the remaining 1 cup sugar, 1/2 teaspoon cinnamon and 1/2 teaspoon anise in a baking dish.
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14
Working in batches, pipe 6-inch strips of the dough into the hot oil and fry until golden brown, turning once.
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15
Remove with a slotted spoon or spider to the prepared paper towel-lined baking sheet.
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16
Let the churros drain for 30 seconds and immediately toss in the sugar mixture.
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17
Serve the churros warm with the chocolate dipping sauce on the side.
