In a large bowl, whisk together the flour, sugar, salt, and active dry yeast.
Pour the warm milk into the dry ingredients, then add the egg, melted butter, and vanilla extract.
Mix all ingredients until just combined, then knead the dough for 8-10 minutes until it becomes smooth and elastic.
Cover the dough and let it rise in a warm place for about 1 hour, or until doubled in size.
Meanwhile, pan-fry the diced pork roll in a skillet until lightly browned. Combine with grated cheese and ground black pepper.
On a lightly floured surface, roll out the dough to about 1 cm (approximately 1/2 inch) thickness. Use a glass or doughnut cutter to cut out circles.
Place a small amount of the pork roll and cheese mixture in the center of each dough circle. Fold the dough in half to form a half-moon shape, and seal the edges well to prevent the filling from escaping during frying.
Place the filled doughnuts on a baking sheet lined with parchment paper, and cover with a clean kitchen towel. Let them rise for an additional 30 minutes.
In a large pot, heat the oil to approximately 340°F (170°C). Test the oil by dropping in a small piece of dough; it should immediately float to the surface and gently sizzle.
Fry the filled doughnuts for 2-3 minutes per side, until golden brown. Use a slotted spoon to remove them from the oil, and place them on paper towels to drain excess oil.
While still slightly warm, drizzle the tops of the doughnuts with maple syrup and sprinkle with a little powdered sugar for a sweet and savory flavor.
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