Trim ends from acorn squash and carefully halve from pole to pole. Use a spoon to scoop out strings and seeds. Cut halves into ½" slices.
Stem and finely chop rosemary.
Pat chicken breasts dry, and season both sides with ½ tsp. salt and ¼ tsp. pepper.
Roast the Squash
Place acorn squash on baking sheet and toss with 1 Tbsp. olive oil, Parmesan, rosemary, and a pinch of salt. Massage oil into squash. Spread into a single layer.
Roast in hot oven until tender, 18-23 minutes.
While squash roasts, cook chicken.
Cook the Chicken
Place a medium non-stick pan over medium heat and add 1 tsp. olive oil.
Add chicken breasts to hot pan, and cook until browned and chicken reaches a minimum internal temperature of 165 degrees, 5-7 minutes per side.
Remove chicken to a plate and tent with foil.
Make the Sauce
Return pan used to sear chicken to medium heat. Add sherry wine to hot pan and cook until liquid is reduced by half, 30-60 seconds.
Stir in demi-glace and cranberry sauce until combined. Swirl in butter.
Remove from burner. Add chicken to pan and flip to coat.
Finish the Dish
Plate dish as pictured on front of card, spooning any remaining sauce over chicken Bon appétit!