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To prepare brine: Place brown sugar, 1/4 cup salt and 1 tablespoon cumin in a heatproof bowl. Pour in boiling water and stir to dissolve. Stir in ice cubes until melted.
To butterfly & brine pork: You’re going to double butterfly the pork loin so it can be flattened, stuffed and rolled. To do so, place pork loin on a cutting board. Holding the knife blade flat, so it’s parallel to the board, make a lengthwise cut into the side of the roast just above the center, stopping short of the opposite edge so that the flap remains attached. Rotate the tenderloin 180 degrees. Still holding the knife parallel to the cutting board, make a lengthwise cut into the side opposite the original cut, just below the center, taking care not to cut all the way through. Open up the two cuts so you have a large rectangle of meat. Cover with plastic wrap and pound to an even thickness of about 1/2 inch. Place the pork in a sealable gallon-size plastic bag and pour in the brine; turn to coat. Place in a dish and refrigerate for at least 2 hours and up to 4 hours.
To prepare stuffing: About 1 hour before you stuff the pork, heat 2 tablespoons oil in a large skillet over medium heat. Add poblanos, sweet potato, apple, 3 cloves garlic, 1/2 teaspoon cumin, 1/4 teaspoon salt and 1/8 teaspoon each pepper and chipotle and cook, stirring, until the potato is just tender, 12 to 15 minutes. (Add water by the tablespoon to prevent sticking, as needed.) Remove from the heat and let cool for about 15 minutes.
To rub & roast pork: Line a large baking pan with foil and coat with cooking spray. Remove the pork from the brine and thoroughly pat dry. Combine 2 tablespoons oil, 2 cloves garlic, cilantro, chipotle and 1/2 teaspoon pepper in a small bowl. Mix thoroughly, then rub the mixture all over the pork. Spoon the stuffing mixture over the pork, leaving a 1-inch border all around. Roll up from long side to long side and secure in several spots with kitchen string. Transfer to the prepared pan seam-side down and let stand at room temperature while the oven preheats, 15 to 20 minutes.
Preheat oven to 375°F.
Roast the stuffed pork until an instant-read thermometer inserted into the meat (not the stuffing) registers 145°F, 45 minutes to 1 hour. Let rest on a cutting board for 15 minutes. Remove the string and slice the pork into thick rounds.