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Inside-Out Cuban Pork Tenderloin Roll

Inside-Out Cuban Pork Tenderloin Roll
  • Prep 30 min
  • Total 1 hr 5 min
  • Servings 4
Your favorite sandwich just got a major makeover in the form of this brilliant pork tenderloin roll. It comes loaded with all the classic Cuban ingredients and, of course, that includes pickles.
Updated April 23, 2019

Ingredients

Sweet Mustard Sauce and Glaze

  • 4 tablespoons butter
  • 1/4 cup packed brown sugar
  • 1/4 cup yellow mustard
  • 1 tablespoon chili powder

Pork Tenderloin

  • 4 (10-inch) pieces cooking twine
  • 1 1/4 lb pork tenderloin, trimmed
  • 3 thin slices Swiss cheese
  • 3 thin slices gluten-free Black Forest ham
  • 1/2 cup dill pickle slices
  • 2 cloves garlic, finely chopped
  • 1 tablespoon vegetable oil
  • 1/2 teaspoon salt
  • 1/2 teaspoon ground black pepper

Steps

  • 1
    Heat gas or charcoal grill. Soak twine in water 10 minutes to prevent burning. Meanwhile, in 2-quart saucepan, melt butter over low heat. Stir in brown sugar, mustard and chili powder. Cook 2 to 3 minutes, stirring frequently, until mixture comes to a boil. Pour 1/4 cup sauce into small bowl; reserve for serving. Leave remaining sauce in saucepan for basting pork.
  • 2
    Insert knife one-third of way up from bottom of tenderloin along 1 long side and cut horizontally, stopping 1/2 inch before edge. Open up flap.
  • 3
    Keeping knife parallel to cutting board, cut through thicker portion of tenderloin about 1/2 inch from bottom of tenderloin, keeping knife level with first cut and stopping about 1/2 inch before edge. Open up this flap.
  • 4
    Press sides of tenderloin down so it lies flat. Cover with plastic wrap; pound with flat side of meat mallet to 1/2 inch thick.
  • 5
    Place cheese down center of tenderloin; top with ham.
  • 6
    Arrange pickles on top of ham. Sprinkle garlic evenly over filling.
  • 7
    Tightly roll up tenderloin lengthwise.
  • 8
    Tie tenderloin tightly with twine.
  • 9
    Brush tenderloin with oil, then rub in salt and pepper. Place seam side up on grill over medium heat. Cover grill; cook 15 minutes.
  • 10
    Turn pork; brush with remaining glaze in saucepan and grill 10 to 15 minutes longer or until meat thermometer inserted in center of tenderloin reads 145°F. Transfer to cutting board; cover with foil, and let stand 5 minutes. Cut and discard twine. Cut tenderloin into slices with serrated knife. Serve with the 1/4 cup reserved sauce.

Expert Tips

  • Worried about keeping the tenderloin tightly rolled while tying? Use toothpicks to secure edge before tying with twine. Remove toothpicks before grilling.
  • Like it hot? Use spicy dill pickles instead of plain.
  • Cooking Gluten Free? Always read labels to make sure each recipe ingredient is gluten free. Products and ingredient sources can change.

Nutrition Information

Nutrition Facts

Serving Size: 1 Serving
Calories
510
Calories from Fat
270
Total Fat
30g
46%
Saturated Fat
14g
72%
Trans Fat
1/2g
Cholesterol
150mg
49%
Sodium
1180mg
49%
Potassium
690mg
20%
Total Carbohydrate
18g
6%
Dietary Fiber
1g
6%
Sugars
14g
Protein
43g
% Daily Value*:
Vitamin A
25%
25%
Vitamin C
0%
0%
Calcium
25%
25%
Iron
10%
10%
Exchanges:
0 Starch; 0 Fruit; 1 Other Carbohydrate; 0 Skim Milk; 0 Low-Fat Milk; 0 Milk; 0 Vegetable; 4 Very Lean Meat; 1 Lean Meat; 1 High-Fat Meat; 3 1/2 Fat;
Carbohydrate Choice
1
*Percent Daily Values are based on a 2,000 calorie diet.
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