In a medium mixing bowl, whisk together the milk, chocolate pudding mix, and the instant espresso. Use hand mixer to mix ingredients.
Preheat oven to 400 degrees F.
Unroll phyllo dough and remove sheets. Working with 1 sheet at a time, lay out and spray phyllo sheet with cooking spray. Sprinkle with 1/4 teaspoon cinnamon-sugar. Lay next sheet on top and repeat steps. With a pizza cutter or sharp knife, cut dough into 8 rectangles, approximately 4 by 5 inches. Fit rectangles into muffin cups and bake for 8 to 10 minutes, or until golden brown.
Remove phyllo cups from oven and let cool for 10 minutes. Remove cups from pan and cool completely.
Spoon or pipe mocha pudding into cups and top with a 1 tablespoon dollop of whipped topping. Sprinkle with cocoa powder.
Cook's Note: Keep phyllo dough covered when not using, as it dries out quickly.