Heat the oven to 375°F (190°C), arrange the potatoes on a parchment-lined large baking pan, pierce their tops with a fork, and roast for 45–55 minutes before cooling enough to handle. A fork should enter the flesh easily, with no hard center.
Gently press each warm potato from above to flatten its base, remove a slice of skin from the top, and spoon out the interior while retaining a ½-inch wall. The hollowed potato should sit level and hold its bowl shape.
Mash or blend ½ cup of the removed flesh, using additional mashed flesh to press closed any accidental holes in the shells. The measured puree should have no firm lumps, and each patch should close the opening.
Use a large pitcher or measuring cup to stir the yolks, custard sugar, and measured puree into a uniform mixture. Look for an even color without streaks of yolk or pockets of potato.
Stir in the salt, cinnamon, vanilla, whipping cream, and milk without beating air into the mixture. The filling should pour smoothly rather than carry a thick cap of foam.
Distribute the filling among the potato bowls, reserving any excess for a ramekin baked by the water-bath method below. Check that the shells remain level and that no filling leaks onto the pan.
Reduce the oven to 340°F (170°C), bake for 20–25 minutes with adjustments for potato size, then cool completely and refrigerate for 2–4 hours or overnight until set. At the end of baking, the perimeter should hold still while the center trembles like soft gelatin rather than sloshing like liquid.