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Grease a large bowl with cooking spray and set aside. In a small, microwave-safe bowl or glass measuring cup, add milk. Microwave until lukewarm, 40 seconds. Add a teaspoon of sugar and stir to dissolve, then sprinkle over yeast and let sit until frothy, about 8 minutes. In a medium bowl, whisk together flour and salt. In a large bowl, whisk together remaining sugar, butter, eggs, and vanilla with a wooden spoon. Pour in yeast mixture, mix to combine, then add in dry ingredients, stirring with a wooden spoon until a shaggy dough forms. Transfer to a lightly floured surface and knead until elastic and only slightly tacky, adding more flour a teaspoon at a time if needed, about 5 minutes. Form into a tight ball then place dough in oiled bowl and cover with a clean dish towel. Let dough rise in a warm spot in your kitchen until doubled in size, about 1 hour. Line a large baking sheet with parchment. Punch down dough, then turn onto a lightly floured work surface and roll out into a ½” thick rectangle. Using a doughnut cutter or 3” and 1” biscuit cutters, punch out your doughnuts. Re-knead scraps together and punch out as well. Place doughnuts and holes onto baking sheets, cover with dish towel, and let rise again, about 40 minutes more. Make glaze: In a large bowl, whisk together milk, powdered sugar, and vanilla until smooth. Set aside. Line a large baking sheet with paper towels. In a large dutch oven over medium heat, heat 2'' oil to 350°. Cook doughnuts, in batches, until deeply golden on both sides, about 1 minute per side. Holes will cook even faster! Transfer doughnuts to paper towel-lined baking sheet to drain and cool slightly. Dip into glaze, then place onto a cooling rack (or eat immediately!).