• Position a rack in the center of the oven and preheat to 325°F. Line two baking sheets with parchment paper.
• In a small bowl, whisk together the flour, baking powder, baking soda, salt, and spices; set aside. In a large bowl, whisk the eggs and sugar until the mixture looks smooth and slightly paler, about 1 minute. Whisk in the oil, pumpkin, and vanilla until evenly combined. Add the dry ingredients and stir just until incorporated.
• Use a scant 1/4-cup measuring cup or 1/4 cup cookie scoop to portion the dough onto the prepared baking sheets, leaving about 3 inches between each mound.
• Bake one sheet at a time until the tops are set and a toothpick inserted in the center comes out clean, 14 to 16 minutes. Let the cookies rest on the sheet for 5 minutes, then transfer to a wire rack to cool completely.

Frosting

• In a very small bowl or ramekin, combine the instant espresso and half of the milk. Mix to dissolve the espresso and set aside.
• In a large bowl, add the confectioners’ sugar, half of the milk (1.5 tablespoons), corn syrup, vanilla extract, salt, and boiling water. Whisk until smooth. Separate the frosting into two bowls. To one bowl, add the chai spice and mix until smooth. To the other bowl, add the bloomed espresso powder. Since every brand of confectioners’ sugar behaves differently, add 1 to 2 tablespoons more water if the frosting seems thick. It should run off a spoon slowly. Taste both frostings, both espresso and chai are strong so the recipe calls for the smallest amount for stronger flavor increase by 1/4 teaspoon at a time. If increasing the espresso, make sure to dissolve the additional in 1 teaspoon of water first.
• Flip the cooled cookies so the flat side is facing up. Using an offset spatula, spread the espresso frosting over half of each cookie. Continue frosting all cookies with the espresso frosting in the same way. Clean or wipe off the offset spatula and spread the chai frosting over the other half of the cookie. Continue until all cookies have an espresso side and a chai side. Let the frosting set before enjoying.