2 1/4 cups all-purpose flour
1/2 cup unsweetened cocoa powder
2 teaspoons cream of tartar
1 teaspoon baking soda
1/2 teaspoon kosher salt (or ¼ tsp table salt)
1 cup (2 sticks) unsalted butter, room temperature
1 3/4 cups sugar (divided)
2 large eggs
2 teaspoons cinnamon (divided)
1/2 teaspoon ground chipotle powder (divided)
Preheat oven to 400 degrees, with racks in upper and lower thirds. In a medium bowl, sift together flour, cocoa powder, 1/4 tsp. chipotle powder, 1 tsp. cinnamon, cream of tartar, baking soda, and salt. In a large bowl, using an electric mixer, beat butter and 1 1/2 cups sugar on medium speed until light and fluffy, about 2 minutes. Scrape down side of bowl. Add eggs and beat to combine. With mixer on low, gradually add flour mixture and beat until combined.
In a small bowl, combine remaining 1/4 cup sugar, 1 tsp. cinnamon, and 1/4 tsp. chile powder. Using heaping tablespoons, form balls of dough and roll in cinnamon-sugar mixture. Place, about 3 inches apart, on parchment or silicone-lined baking sheets. Bake until cookies are set in center and begin to crack, about 10 minutes. Let cookies cool on sheets on wire racks 5 minutes, then transfer cookies to racks to cool completely. (Store in an airtight container, up to 1 week.)