This kind of recipe's normally made with just chocolate, and maybe a little peppermint. But that's been done before. It's boring. Delicious, but boring. My recipe's only the former, but definitely not the latter. —Fresh Beats, Fresh Eats
Grind the star anise with a mortal and pestle or a spice grinder. Make sure you REALLY grind the pods, you don't want any pieces sticking out of your cookies.
Put the ground anise in a bowl with the flour, cocoa, salt, espresso powder, and baking powder, and whisk it all together.
Mix the vegetable oil and sugar (just the regular sugar, not the powdered sugar, that's for later) for a couple of minutes in a stand mixer.
Add the eggs, vanilla, and grapefruit zest, and mix in with the sugar/oil until combined.
Next, add all your dry ingredients and mix together with the wet stuff, then refrigerate the dough overnight.
Preheat your oven to 350.
Put your powdered sugar into a bowl. Roll your dough into inch-wide balls, then roll them in the powdered sugar. Make sure you get a LOT of powdered sugar on the cookies, you don't want any black parts showing.
Put the cookies on a baking sheet with parchment paper, stick them in the oven for 10 minutes, let them cool for 5 minutes, then put them on a cooling rack.