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Make the cheesecake center: Combine all ingredients in bowl, scoop into 12 equal balls, freeze until solid.
Cook 3 peaches to reduce water content. Save your other 2 for slicing ontop! Dice them into about ¼-inch pieces. Spread them in a single layer on a parchment-lined sheet. Dust with some cane sugar. Roast at 375°F for about 20-30 minutes, stirring once halfway through. You want them soft, fragrant, and noticeably less juicy, with some caramelization around the edges. Let them cool completely. If there’s liquid on the pan, drain it and gently pat the peaches dry before adding them to the dough.
Cookie dough: Beat the softened butter with sugars. Mix in eggs, egg yolk, molasses, vanilla bean paste. Combine all dry ingredients (flour, oats, cornstarch, baking soda, salt, cinnamon) and fold into the wet mixture. Fold in cooked cooled peaches.
Assembly: Scoop your chilled cookie dough (about 2½–3 Tbsp per cookie). Flatten slightly. Add cheesecake filling in the center. Enclose by folding the dough around it. Roll gently into a ball. Chill the stuffed cookies overnight.
Baking: Preheat oven to 325 degrees. Flatten cookies slightly and place on parchment paper. Place 2 sliced peaches on each cookie and dust w cane sugar. Bake for 12-15 minutes until cookie is golden and cheesecake center is still gooey.