Sift the flour, cocoa, baking soda, cinnamon, and salt into a medium bowl; whisk to combine and set aside.
Melt the butter in a small saucepan over medium heat until fully liquefied and just starting to foam; take off the heat and cool 3–5 minutes. Scrape into a large mixing bowl.
Whisk the granulated sugar and molasses into the warm butter until glossy, then whisk in the espresso powder to dissolve. Add the eggs one at a time, whisking well after each until the mixture thickens slightly. Stir in the vanilla.
Switch to a flexible spatula and fold the dry mixture into the wet in two additions just until no dry streaks remain. The dough will be soft and sticky.
Scrape the dough onto a sheet of parchment and pat into a 1-inch-thick slab. Wrap and chill until firm enough to scoop, 45–60 minutes (or freeze 20 minutes for a quick set).
Heat the oven to 325°F (165°C). Line two baking sheets with parchment. Place the rolling sugars into separate shallow bowls.
Scoop 1 1/2-tablespoon portions (about 25 g), roll quickly into balls, coat lightly in granulated sugar, then roll generously in powdered sugar. Arrange 2 inches apart on the prepared sheets. For bolder crinkles, roll each ball a second time in powdered sugar just before baking.
Bake one sheet at a time for 12–14 minutes, rotating halfway, until edges are set and tops are deeply cracked but centers still look soft.
Cool on the sheet for 6 minutes, then transfer cookies to a rack to finish cooling. The centers will settle into a fudgy texture as they cool.