Preheat the oven to 400 degrees F and cut acorn squash lengthwise, remove seeds and sprinkle cinnamon all over the inside of the squash.
Spray baking sheet with non-stick cooking spray and place acorn squash down. Bake for about 40 minutes or until squash is soft and mushy.
Wait for squash to cool and spoon out into bowl. Sprinkle with desired amount of salt and pepper.
Heat olive oil in frying pan on medium heat.
Take two whole wheat tortillas. On one tortilla, spread 2-3 tablespoons of squash all over. Add 2-3 tablespoons of black beans on top of squash, sprinkle with red pepper flakes and cilantro then place tortilla in oiled frying pan.
On the other tortilla, spread desired amount of cheese all over. Place on top of the tortilla in the frying pan.
Fry about 2 minutes on each side or until crispy and golden brown, repeat for more quesadillas.
Cut into triangles and serve with sour cream and hot sauce. Serves 2, 2 triangles each.