Heat oven to 450° F. Place the squash halves cut-side down in a baking dish, add 1/4 inch water, cover with foil, and bake until tender, 25 to 30 minutes.
Spray a large, nonstick skillet with nonfat cooking spray. Add in onion, garlic, and 2 tbsp broth and saute until onions begin to become transparent about 3-5 minutes.
Add in ground pork, salt, pepper, cumin, paprika, and chipotle seasoning. Cook until pork is cooked through and no longer pink, about 5-7 minutes.
Turn heat to low and add in diced tomatoes, tomato paste, and chiles. Cover and cook for about 15 minutes or until most of the liquid has minimized, stirring occasionally.
Fill the hollow of each acorn squash half with 1/4 of the ground pork mixture.
Top with 2 tbsp fat-free sour cream, and garnish with fresh chives or cilantro.