Preheat an oven with a rack in the middle to 400˚.
There are a few ways you can core the squash depending on how large they are.
EASY: Slice in half and then take a little off each end to make a flat bottom. Use a small spoon to dig out the seeds. Slice into ¼-½" slices.
PRETTY BUT A LITTLE MORE TIME: Slice in half and then slice into ¼-½" slices. Use an an apple corer to work your way around the interior removing the seeds and making a pretty scalloped interior ring that matches the outside.
EASIEST: Slice the squash in half from root to stem. Use a spoon to scoop out the seeds. Slice along the short side making half moons of squash.
Either way, discard the seeds or feed the birds if you like!
Drizzle a baking sheet with 1 tablespoon of olive oil.
Lay the squash on the baking sheet in a single layer making sure to leave room between the slices.
Turn the squash slices over. Drizzle with second tablespoon of olive oil.
Start seasoning the squash by sprinkling all the seasoning on the squash starting with the ancho chili powder. End with a generous sprinkling of salt.
Bake in preheated oven for 25 minutes until crispy and golden. Flip halfway through baking as needed.
Remove to a baking rack to cool and keep crisp.
Add to a serving platter and sprinkle with cranberries. Drizzle with balsamic syrup (optional).
Serving and Storage
Store any leftovers in a sealed container or bag.
Refrigerate for up to 3 days.
Make ahead. Roasted delicata squash is great to make ahead of time for the holidays. Roast it for a few hours before you plan to serve it. Transfer it to a rack on the baking sheet so it doesn't get too soft. You can even pop it back in the oven for a few minutes at 350˚ right before serving on the rack to crisp it up.Reheat Instructions. Place on a rack in a baking sheet and heat at 350˚ until warmed.Freezing. Freeze it in an individual layer on a baking sheet and then transfer to a freezer-safe storage bag.