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1
Boil the potatoes until they are soft enough that a fork can easily pierce through them, about 15 minutes.
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2
Drain and mash the potatoes with a masher or hand mixer until smooth.
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3
Combine the cheddar and garlic, then mix into the potatoes until incorporated.
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4
Add all of the dough ingredients into a food processor and pulse until well-combined. If the dough is sticky, add a bit more flour and if it's too crumbly, add more milk. (You may have to do this in two batches, depending on the size of your food processor.)
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5
Remove the dough from the processor and transfer it to a floured surface. Divide the dough into 4 equal parts and wrap 3/4 of the dough in a damp kitchen towel and set aside.
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6
Roll one of the four parts of dough into a rectangle shape on the floured surface, until it's about 1/4- to 1/2-inch thick, and place over a pierogi mold. (Alternatively, if you use a pasta maker instead of rolling it out by hand, I recommend keeping it on the 7 setting and just running it through two times to achieve a smooth texture.)
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7
Fill each pierogi with a tablespoon of the filling, then place another layer of dough over the top.
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8
Push a rolling pin over the dough to seal the dumplings in the pierogi press, then either press down on the pierogi maker to form the dumplings, or use a fork to press the edges together.
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9
Transfer dumplings to a floured baking sheet and set aside.
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10
Repeat with the rest of the filling and dough.
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11
Bring a large pot of salted water to a boil, and boil the pierogi until they float to the top of the water, roughly 3 to 5 minutes. Remove the pierogi and set aside. They're ready to eat as soon as they reach room temperature.
