Step 1

Place the piloncillo in a small saucepan along with the cinnamon stick. Cover with 1 cup water and set over low-medium heat, and let it cook and strongly simmer, covered with a lid, for about 10 minutes. Remove the lid, the piloncillo should be mostly dissolved, and continue cooking at a strong simmer, now uncovered, for another 3 to 4 minutes. Strain the piloncillo syrup into a measuring cup and discard the cinnamon stick. (You should have about ½ cup. If you have less, add a bit of water. If you have more, use only ½ cup.) Set aside.

Step 2

In a bowl, mix the all-purpose flour, masa harina, and salt.

Step 3

In the bowl of a stand mixer set with the paddle attachment, beat the butter and vegetable shortening over medium speed for 3 to 4 minutes until very creamy. Reduce speed to low, add the piloncillo syrup (it may have solidified a little bit, but it should still be soft and malleable) and continue beating for a minute until it incorporates. Add the egg and beat for another minute until it is completely incorporated.

Step 4

Using a large spoon or measuring cup, add the flour mixture in batches. Lastly, add the milk and continue beating for a minute or two until you have a soft, malleable, and homogeneous dough. Gather it into a ball, wrap it in plastic wrap, and refrigerate anywhere from 30 minutes to 24 hours.

Step 5

When ready to bake, remove dough from refrigerator. Place two racks in the upper and lower thirds of the oven and preheat to 350℉. Cover two large cookie sheets with parchment paper.

Step 6

To make the coating, in an extended bowl, mix the sugar with the cinnamon.

Step 7

Generously flour your countertop, your hands, and a rolling pin. Split the dough into four pieces. One at a time, roll the dough out to about ⅓-inch thickness. You may flip it gently once or twice as you do. The dough will look as if it cracks as you roll, that is ok! You can pinch it or press it back together.

Step 8

Use a cookie cutter of any shape you like, to cut the dough into pieces of about 2-inches in diameter. One by one, dip the cookies, gently, as they may want to crumble, in the cinnamon sugar mixture.

Step 9

Place on the parchment-lined cookie sheets and bake for 20 minutes, until they turn a light golden brown on the edges. Remove from the oven, sprinkle more cinnamon sugar on top if you want, and let cool.