Make sure to make room in your refrigerator for one baking tray and in freezer before making the dough and piping the cookies. These cookies need to chill before baking and if you chill the dough prior to piping, it will become too stiff to pipe and won't easily squeeze out of the piping bag.Line 1 or 2 cookie trays (as needed) with parchment paper and set aside. Now in the bowl of a stand mixer, beat butter and confectioners' sugar together till they get very light and fluffy, for about 3-4 minutes on med-high speed.
1 Cup Butter, 1 and ¼ Cups Confectioners' sugar
Next add in the egg and vanilla too. Beat for about a minute on high speed. Scrape the sides and bottom of the bowl as required.
1 large Egg, 2 teaspoons Pure vanilla extract
Keeping mixer on low, slowly add in sifted flour, salt and cocoa powder. Turn the mixer to med-high and beat till the dough comes together. Now mix espresso powder in warm milk till it gets mixed well and pour that in the mixing bowl.
2 cups All purpose flour, ⅓ cup Unsweetened cocoa powder, ⅛ teaspoon Salt, 1 teaspoon Espresso Powder, 2 Tablespoons Milk
You want the dough to be creamy but not too soft or runny. So don't be tempted to add a lot of milk to it. Now in a piping bag, fitted with a large piping tip spoon just a few tablespoons of dough to test if the dough is pipeable.
If you are able to pipe cookies, add more dough to the pipping bad and continue to pip cookies. But if the dough is hard to squeeze out of the bag, add about ½ a tablespoon of additional milk to the dough.
Remember the dough might appear stiff, so first few cookies can be hard to squeeze. But as the dough warms up slightly with the warmth of your hands, the task will get easier. Therefore, don't add too much milk in the dough at a time.
Refrigerate piped cookies for 20-25 minutes and then you can lift them up using a spatula and transfer them on a larger plate to chill them in the freezer to make them extra firm.Chill them in the freezer, then transfer back to parchment lined cookie tray. Keep some space between each cookie to allow them to spread.. As the cookies chill, preheat oven to 350°F (177°C). Bake the cookies for about 12-14 minutes or till they appear set on the edges. If you pipe smaller cookies, they will get baked in around 12 minutes.
Once baked, allow to cool on cookie trays for about 4-5 minutes and then transfer on a wire rack to cool completely. Press candied cherry halves on each cookie as they are cooling.
16 whole Candied Cherries