1 large butternut squash (2 lb), peeled, seeded and cut into 1-inch chunks
1/2 tsp sea salt, divided
1 tsp fresh ground black pepper, divided
4 5-oz boneless, skinless chicken breasts
1/2 tsp dried thyme
1/2 cup plus 2 tbsp 2% milk, divided
3/4 tsp chile powder (NOTE: Opt for ancho chile powder, if available.)
1/4 tsp ground cinnamon
1/2 tbsp organic unsalted butter
1 tbsp brown rice flour (NOTE: If available, opt for the superfine variety.)
1 1/2 oz crumbled reduced-fat blue cheese
1/4 cup dried unsweetened or naturally sweetened cranberries
2 tbsp chopped fresh parsley leaves
Arrange racks in upper and lower thirds of oven and preheat to 425˚F. Line 2 large, rimmed baking sheets with foil and mist with cooking spray. Add squash to 1 sheet, mist with cooking spray and sprinkle with 1/4 tsp salt and 1/2 tsp pepper; toss and spread in a single layer. Add chicken to second sheet, lightly mist with cooking spray and season with thyme and remaining 1/4 tsp salt and 1/2 tsp pepper. Roast squash for 20 to 25 minutes, tossing once or twice, until lightly browned and very tender. Roast chicken for 15 to 20 minutes, turning halfway, until no longer pink in center and juices run clear.
Wrap chicken in foil to keep warm. Transfer squash to a food processor. Add 2 tbsp milk, chile powder and cinnamon; process until puréed. Set aside.
In a small saucepan on medium, melt butter. Add flour and stir until moistened; cook, stirring frequently, until lightly toasted, about 1 minute. Slowly pour in remaining 1/2 cup milk. Increase heat to medium-high and bring to a simmer, whisking constantly. Reduce heat to low and simmer, whisking to break up any lumps, until slightly thickened, 1 to 2 minutes. Remove from heat and immediately whisk in cheese. Cover until ready to serve. (NOTE: If you're not serving within 5 minutes, reheat on low. If mixture thickens too much, whisk in more milk to reach desired consistency.)
Divide squash among serving plates. Nestle chicken beside squash and top evenly with sauce. Sprinkle with cranberries and parsley.