Preheat oven to 400F. Place rack in middle position. Prepare sheet pan by lining with parchment paper.

Scrub, rinse, and dry sweet potato. Stick a fork all over the potato multiple times to allow steam to escape.

Rub oil on the surface of the potato. Place on the prepared pan and bake for about 50 minutes, flipping the potato halfway through. Use a toothpick or skewer to check for doneness; the toothpick should slide easily into the potato with no resistance. If not done, bake for a few more minutes.

Remove potatoe from the oven and let cool slightly on parchment paper, about 20 minutes (until still warm but able to handle). Carefully remove the skin from potatoes. You should have 2/3 cup of mashed potatoes. (You can gently press on them with a fork or whisk and measure them into a measuring cup.)

While warm, place the potato in the bowl of a stand mixer, fitted with the whisk attachment. Turn the mixer on medium low for about 20 seconds then stop. (Once you start to mix the baked potato, long little stringy pieces will attach to the whisk; you'll want to rinse the whisk to get rid of those. Removing them makes the filling super smooth, so you're not eating the stringy parts.) Repeat these two or three times, each time rinsing the strings from the whisk.

Add the butter to a skillet over medium heat. Add in sugar and stir together and cook until sugar is dissolved. Stir in pecans and cook for about 5 minutes. (Watch closely so they don’t burn.) Remove from heat and allow to cool, about 10 minutes.

Add cream cheese to the bowl of the stand mixer. Beat on medium speed then slowly add in sweetened condensed milk, cinnamon and vanilla extract and mix until completely smooth.

Turn off mixer and fold the whipped cream into the cream cheese mixture using a spatula.

Line an 8x8 pan with one piece of plastic wrap, with at least four inches of overhang. Then layer in another piece of plastic wrap going the other direction.

Pour in ½ of the ice cream mixture, then ½ of the caramel sauce, then ½ of the butter pecan mixture. Using a butter knife, create a swirl pattern.

Pour in the remaining ice cream, caramel, then pecans, and swirl again. Pull each side of the plastic wrap to cover the top of the ice cream, then cover fully with another piece of plastic wrap. Place in the freezer for 6-8 hours. When ready to serve, remove from the freezer and allow it to defrost for 10 minutes. Scoop and serve!