Preheat oven to 425°F.
Pour the remaining sweetened condensed milk into a 9’’ pie plate and cover with foil (be sure to reserve 1/4 cup for later use).
Place the pie plate in a shallow baking or roasting pan. Add approx.1-inch of hot water to the pan and place in the preheat oven.
Bake for 45-50 minutes or lightly caramel-colored, slightly darker than beige. Remove from the oven and set aside to cool to room temperature.
Reduce oven temperature to 350°F.
While the caramel is cooling, remove the crescent rolls from their packaging. Unroll and separate each crescent triangle onto a clean surface.
Place a peach slice at the widest part of the crescent triangle and roll, concealing the peach (a little peach showing on the edges it ok). Repeat for the remaining peach slices and dough.
Once the caramel has cooled, pour into a 13×9-inch casserole dish, spreading evenly along the bottom.
Place the peach dumplings on top of the caramel sauce, giving each dumpling a little space so they can evenly brown.
Brush the tops of the dumplings using the reserved 1/4 cup of sweetened condensed milk and sprinkle with 1 teaspoon of ground cinnamon.
Place in the oven and bake for 40-50 minutes or until the dumplings have turned a nice golden brown and the caramel sauce has deepened in color. Remove from the oven and set aside to rest for 5 minutes.
While the dumplings are resting, place the heavy cream and remaining cinnamon in the bowl of an electric mixer fitted with a whisk attachment. Whisk until stiff peaks form and transfer to a piping bag or serving bowl.
To serve, spoon dumplings on to serving plates (making sure to collect all that fabulous caramel at the bottom of the pan) and pipe or dollop with a little bit of the cinnamon whipped cream.