Heat 2 cups milk in the microwave or on the stovetop until it reaches 100 F. Add ½ cup sugar, 1 teaspoon salt, vegetable oil, and ½ cup butter.
Cool to lukewarm and add the yeast, vanilla extract, and 2 teaspoons cinnamon. Stir gently.
Alternating between them, mix in half the flour, then two of the eggs and then the remaining flour to the wet mixture. Mix thoroughly, pull into a ball and lightly knead.
Continue kneading the dough until a smooth ball forms, about 5 minutes.
Cover and let rise for 1 hour.
Mix together the softened cream cheese, 2 tablespoons milk, 2 tablespoons sugar, and 1 teaspoon cinnamon to form a thick cream.
Whisk together the remaining egg and a teaspoon of water to form an egg wash.
Divide the dough into 12 balls. Cover and let rise 1 hour.
Preheat the oven to 425 F.
Flatten each ball.
Use your finger to make a dent in the center of each ball for the filling.
Add about 1 tablespoon of cream cheese filling to each roll
Top each roll with 3-4 cherries from the cherry pie filling.
Brush each roll with the egg wash.
Bake in the preheated oven for 15-20 minutes or until golden brown.
Allow to cool slightly and serve with a sprinkle of powdered sugar if desired.