Prepare the pork chops. Season pork chops with salt, pepper, and Italian seasoning on both sides. Set aside.
Melt 2 tablespoons of butter of medium-high heat in a large skillet. Carefully add the pork chops to the skillet and cook, undisturbed, on each side for approximately 5-6 minutes (time will vary depending on thickness). The outside should be golden-brown and the internal temperature should register nearly 145 degrees F with a digital meat thermometer. Transfer pork chops to a plate and set aside.
To the same skillet, add one more tablespoon of butter and the butternut squash. Stir well to coat the squash. Cook the butternut squash for approximately 5-8 minutes, stirring frequently. Add the onion and continue to cook until onion turns soft and translucent approximately 3-5 minutes.
Once the butternut squash just starts to soften (but isn't quite soft) and the onions are translucent, add the minced garlic, fresh rosemary, brown sugar, and cinnamon to the butternut squash. Mix well to combine. Cook for 1-2 minutes.
Add the spiced apple cider and sliced apples and stir well to mix. Return the pork chops to the skillet, tucking in between the squash and apples. Allow everything to cook together for approximately 3-4 minutes, or until pork registers a final 145 degrees F.
Top each pork chop with the remaining tablespoon of butter and remove from heat. Serve with mashed potatoes or cauliflower, if desired. Enjoy!