Evenly stagger two racks in the oven and preheat to 400°F.
Pierce the honeynut squash a few times with a knife, then add it to a baking sheet and roast for 30-40 minutes at 400°F, or until soft. If you are using canned purée, skip this step.
When the squash is done, remove it from the oven and decrease the oven temperature to 350°F convection (375°F standard).
While the squash is roasting, prepare the other fillings. Add the cranberries, ¼ cup water and ¼ cup granulated sugar to a small pot or sauté pan. Bring the mixture to a simmer and simmer for 9-10 minutes, until the cranberries have burst and the sauce is thickened. Set this aside.
In a food processor, add ½ cup of pistachios and 90 grams of chocolate. Pulse until a pistachio 'crumble' forms. It should be the texture of wet sand. Set this aside.
To a large bowl, add the butter, ⅓ cup of brown sugar, 1 cup granulated sugar, and ⅔ cup of your cooked honeynut squash or pumpkin purée. Use an electric mixer to mix this until it is fluffy and smooth, about 3-4 minutes.
Add the 2 cups of flour, 1 teaspoon of salt, ½ teaspoon of baking soda, ½ teaspoon baking powder, ½ teaspoon cinnamon and ½ teaspoon of ground ginger to the bowl. Mix with the electric mixer until everything is well combined and a smooth dough has formed.
Add in the pistachio chocolate and use a spatula to mix it into the dough.
Pour in the cranberry sauce, use a spatula to do a few big 'folds' so the cranberry sauce is a ribbon throughout the dough. Be sure not to overmix!
Use a 3-tablespoon cookie scoop to scoop the dough into 24 balls. You can either chill the dough overnight for an extra-chewy cookie, or you can bake the cookies immediately for 12-13 minutes at 350°F convection.
When they are out of the oven, give the pan a light smack on the counter to help the cookies deflate. Let them cool, then enjoy!
