Preheat oven to 375 degrees F (190 degrees C). Line 2 baking sheets with parchment paper.
Beat 1 1/2 cups sugar, butter, vanilla extract, and salt together in a bowl until fluffy. Beat in eggs; add cream of tartar and baking soda. Beat in cocoa powder, 1/2 teaspoon cinnamon, and cayenne powder. Beat in flour. Stir chocolate chips into the dough.
Mix remaining 1/4 cup sugar and 1/2 teaspoon cinnamon together in a bowl.
Roll heaping tablespoons of dough into balls. Roll balls in the sugar-cinnamon mixture and place on the prepared baking sheets.
Bake in the preheated oven until centers are set and edges crack slightly, about 10 minutes. Cool on baking sheets for 5 minutes.