Preheat the oven to 400 F. Cut the honeynut squash in half, remove the seeds (but save the seeds and set them aside), drizzle lightly with olive oil, sprinkle lightly with salt, and roast cut-side down until tender. This takes about 30 - 35 minutes depending on the size of your squash.
Allow the squash to cool, then scoop out the flesh and mash with a fork.
In a large bowl, whisk together the olive oil, brown sugar, and white sugar until smooth. Add the honeynut squash puree, egg yolk, and vanilla extract. Mix until well combined.
In a separate bowl, whisk together the flour, baking soda, salt, cinnamon, and cayenne pepper.
Add the dry ingredients to the wet, and stir until just combined. Refrigerate for an hour, then scoop the cookies into small balls (about 2 tbsp per cookie). Place them back in the fridge for at least 4 hours, up to overnight.
With the leftover seeds, clean them and pat them dry. Preheat the oven to 325.
Add the seeds to a parchment-lined baking tray, along with a drizzle of olive oil to coat, a dash of cinnamon, and a pinch of salt and cayenne pepper.
Bake for 20 - 22 minutes, stirring occasionally until they are golden and crisp. Allow to cool.
When you’re ready to bake the cookies, turn the oven up to 350 F. Add the cookie dough balls to the baking sheet, leaving plenty of room in between each, and top with a few squash seeds.
Bake for 10 - 12 minutes until the edges are golden and the centers look slightly underbaked. Allow to cool on the tray for a few minutes, then finish cooling on a wire rack.
