Start by melting the Mexican chocolate gently—I prefer using a microwave in 20-second intervals, stirring between each pulse, to prevent scorching and preserve the cinnamon and spice notes. While the chocolate melts, whisk together the flour, cocoa powder, cinnamon, baking powder, and salt in a large bowl. This pre-mixing ensures the leavening and spices are evenly distributed throughout the dough for consistent flavor in every bite.

In a separate bowl, whisk together the canola oil and sugar until the mixture becomes glossy and slightly emulsified—this creates a better texture in the final cookie. Add the room-temperature eggs one at a time, whisking well after each addition to incorporate air and create a cohesive base. Stir in the vanilla extract last. The room-temperature eggs are key here because they blend more smoothly into the oil and sugar, creating a lighter dough.

Pour the warm melted chocolate into the wet ingredient mixture from Step 2 and stir until fully incorporated—the warmth of the chocolate will help it blend seamlessly. Now gently fold in the dry ingredient mixture from Step 1 using a spatula or wooden spoon, stirring until just combined. Be careful not to overmix, as this can develop gluten and make the cookies tough rather than tender with a slight crack.

Cover the dough and refrigerate for at least 1 hour (or up to 24 hours). This resting time allows the flour to fully hydrate, the flavors to meld, and the dough to firm up enough for easier handling. Chilling also prevents the cookies from spreading too much during baking, which helps create that signature crinkled texture.

While the dough chills, preheat your oven to 350°F. Once the oven is ready and the dough has finished chilling, sift the powdered sugar into a shallow bowl. Using a tablespoon or small cookie scoop, form 1½-inch dough balls and immediately roll each one in the powdered sugar until fully coated on all sides. This coating is what creates the beautiful crinkled appearance as the cookies bake and the sugar cracks from the expanding dough.

Arrange the powdered sugar-coated dough balls on a parchment-lined baking sheet, spacing them about 2 inches apart. Bake for 8 to 10 minutes—the cookies are done when the edges are set but the center still looks slightly underbaked. I like to pull mine out right when the edges look firm but the very center jiggles slightly when you gently shake the pan; they'll continue cooking on the hot sheet for a minute or two and will set up perfectly as they cool, giving you that tender, fudgy interior with crispy edges.

Let the cookies cool on the baking sheet for 5 minutes, then transfer them to a wire rack to cool completely. This brief resting time on the sheet prevents breakage while still allowing heat to escape.