Preheat the oven to 400 F. Cut the delicata squash in half, length-wise and scoop out the seeds. Cut the squash into 1/2 inch slices. Cut the red onion in half and then into thin slices.
Transfer the squash and onion to a baking sheet and toss with olive oil, salt, and pepper. Transfer to the oven and cook for 15-20 minutes, until the squash is browning and the onion is cooked through.
While the squash and onion cook, prep the dressing. Add the apple cider to a small pot over medium heat. Cook until the cider has reduced by half, about 5 minutes. Add the reduced apple cider to a small jar or bowl.
Add the olive oil, apple cider vinegar, dijon mustard, garlic powder, salt, and pepper. Stir until well combined.
Cut the persimmon in half, then into 1/2 inch slices.
Add the cooked delicata squash, red onion, persimmon, pomegranate seeds, and pecans to a bowl. Pour the dressing on and toss gently with your hands to combine (tongs are too strong and might tear the squash apart). Top with herbs, serve, and enjoy!