Step 1

Scrape vanilla seeds into a small saucepan; discard pod. Add cream, brown sugar, cocoa powder, espresso powder, and salt and cook over medium-high heat, whisking occasionally, until sugar is dissolved, no lumps of cocoa powder remain, and mixture is simmering, about 4 minutes. Remove from heat and add chocolate, stirring to melt. Keep warm over very low heat until ready to serve.

Step 2

Fit pastry bag with star tip. Whisk cinnamon and 1 cup organic sugar in a medium bowl; set aside.

Step 3

Bring vanilla bean, milk, butter, salt, remaining 1 Tbsp. organic sugar, and ½ cup water to a simmer in a medium saucepan over medium-high heat. Using a wooden spoon, add flour in one go, and vigorously mix until dough comes together, about 30 seconds. Transfer to the bowl of a stand mixer or a large bowl; discard vanilla bean. Let cool slightly.

Step 4

Using a stand mixer fitted with the paddle attachment on medium-low speed, add eggs to dough, one at a time, making sure to incorporate each egg before adding the next (alternatively, stir vigorously with a wooden spoon). Dough will look broken at first; continue to beat, scraping bowl occasionally, until dough is smooth, glossy, and somewhat stretchy (pull off a small piece of dough and stretch it—it shouldn't break). Spoon dough into prepared pastry bag.

Step 5

Pour oil into a large pot to come halfway up the sides. Fit pot with thermometer and heat over medium-high until thermometer registers 350°. Holding bag at an angle so tip is a few inches above surface of oil, squeeze out dough, moving the bag as you squeeze so dough is piped in a 6" length into oil. Using a paring knife, cut off dough at the tip to release into oil. Repeat process to make 4 more dough lengths. Fry churros, turning once and adjusting heat as needed to maintain oil temperature, until golden brown on all sides, 2–3 minutes per side. Transfer to a paper towel-lined baking sheet. Repeat with remaining dough.

Step 6

Toss warm churros in reserved cinnamon-sugar mixture. Serve with warm chocolate sauce and hot chocolate, if desired.