Pre-heat oven to 425 degrees. Warm a sauté pan to medium heat.
Add bacon to sauté pan and begin cooking.
Place squash on parchment lined baking sheet, and into oven (while bacon is cooking). Cook until edges are lightly browned (30-45 minutes) then set aside. *No need to toss in oil, because of how dish comes together. Leave dry, do not season.
Once bacon is fully cooked, remove and let cool. Chop into bite-sized pieces.
Add onion to pan, in remaining bacon grease. Add pinch of salt to help bring out moisture. Cook until fully caramelized, stirring occasionally, on medium to medium-low heat (20+ minutes).
Add apple to pan and cook until just softened (1-2 minutes).
Add cooked squash to pan, stirring to coat evenly with oils and flavors of the dish.
Stir in kale, cooking until bright and tender. Add in crumbled bacon.
Remove from heat and serve.
Store, refrigerated, in airtight glass container for up to 5 days. Re-heat on stovetop.