I really like how your cookie reminded me of a pie my family has at Thanksgiving, both by flavor and visually. I really liked the filing inside of the cookie. I wish there was a little more cranberry flavor to the cookie. I also wish there could be a little “whipped cream” on the top. What if you put the dough like you did, but instead of placing the dough around the cup before it goes in the oven, maybe put a ball of dough on top of the cup and let the hole form itself? I don’t know how it would exactly work, but it might make the crust neater so to speak.