Heat a grill or smoker to 400 degrees F.
Halve the acorn squashes and use a spoon to remove the seeds and stringy pulp. Coat each squash half with olive oil and season generously with Salt Pepper + Three Chiles. Smoke the squashes until tender, about 25 minutes.
Heat a large skillet over medium heat. Add the sausage to the hot pan. Cook, breaking it up into small pieces as you do, until browned and cooked through, about 8 to 10 minutes. Move the stuffing mix to a large mixing bowl. Remove the sausage from the pan to a paper towel lined plate to cool. Melt half the butter in the hot pan and pour over the stuffing mix.
Melt another two tablespoons of butter and onion, celery, and apples. Season the mixture with more Salt Pepper + Three Chiles and cook until tender, about 5 minutes. Add the sausage to the hot pan and then remove from the heat to cool.
Add the broth and eggs to the stuffing mixture to hydrate. Finally combine the sausage mixture with the stuffing mixture and stir to combine.
Remove the squashes from the grill and reduce the heat a bit, aiming for about 325 degrees F. Fill each acorn squash half with ½ to ¾ cup of the stuffing mixture or as much will fit. Any leftover stuffing can be cooked in a small skillet along side the squashes. Return the squash to the grill to cook for another TK minutes or until the stuffing is cooked through and golden brown on top.
Drizzle with more olive and seasoning with parsley and salt just before serving.