Preheat the oven to 350°F/175°C. Position rack to middle.
Line a large baking sheet with parchment paper.
In a large mixing bowl, sift together flour, cocoa powder, baking powder, espresso powder and salt. Set aside.
In the bowl of a stand mixer fitted with the whisk attachment, whisk the eggs on medium-high speed until nice and frothy (about 3-4 minutes).
Slowly add sugar. Continue to whisk until well combined and slightly thickened (about 2 minutes).
Mix in the olive oil and vanilla extract until fully incorporated.
Remove bowl from stand.
Add the sifted dry ingredients and mix with a wooden spoon or rubber spatula until well combined. The dough will be stiff.
Shaping the cookies:Using a churro maker with a star attachment: Pipe the dough into 4-inch strips and shape into S curves on the prepared baking sheet.Without a churros maker: Scoop dough with a medium-sized cookie scoop (approximately 2 tablespoons or 25 grams), roll into a rope, and shape into an S.
Bake for 12–15 minutes, or until the cookies are just set around the edges. Do not overbake.
Transfer cookies to a wire rack to cool completely before icing.
Chocolate Glaze
In a small bowl, whisk the cocoa powder with the hot water until smooth and glossy. Let it sit for about 30 seconds to fully bloom the cocoa.
Add the powdered sugar and vanilla, whisking until combined.
Dip one side of each completely cooled cookie into the icing, let the excess drip off, and immediately sprinkle with a few chocolate jimmies on the dipped side only.
Place on a wire rack and let the icing set.
Video
Notes
Find helpful step-by-step PHOTOS in the post and a SHORT VIDEO in the RECIPE CARD to guide you through the recipe.
Use room-temperature eggs: They mix more smoothly with the olive oil, creating a better, more even dough.
Sift the dry ingredients: Cocoa powder clumps easily; sifting ensures even distribution and a lighter texture.
Watch the baking time closely: Remove the cookies when they're just set around the edges-they'll finish baking on the pan as they cool.
Cool completely before icing: Warm cookies cause the glaze to run off instead of setting properly.
Cookies can be stored in an airtight container for 3-5 days or frozen for up to 3 months.
Please keep in mind that the nutritional information provided below is just a rough estimate and variations can occur depending on the specific ingredients used.