Cuban Sandwich Recipe

Prepare and season pork

Preheat oven to 300°F (150°C). Pat the pork shoulder dry with paper towels. In a small bowl combine 1 cup orange juice, 1/4 cup lime juice, 6 tbsp minced garlic, 2 tbsp olive oil, 1 tsp ground cumin, 1 tsp dried oregano, 1 tsp smoked paprika, 1.5 tsp kosher salt, and 1/2 tsp black pepper. Rub this mixture all over the pork, nestle a bay leaf against the meat and place pork in a roasting pan or Dutch oven.

Add liquid and roast

Pour 1 cup chicken or pork broth into the pan (not over the seasoned top to preserve the rub). Cover tightly with a lid or foil and roast in the preheated oven for 3 to 3 1/2 hours, until pork is very tender and shreds easily with forks. Check once after 2 hours: if the pan looks dry, add up to 1/4 cup more broth or water.

Shred and rest

Remove pork from oven, transfer to a cutting board or bowl and let rest 10 minutes. Using two forks, shred the pork into bite-sized strands. Taste and adjust seasoning with salt and pepper. If desired, reserve 1/4 cup of the pan juices and stir into shredded pork to keep it moist.

While the pork rests, place 1/2 cup packed cilantro leaves, 1/4 cup orange juice, 2 tbsp olive oil, 1 tbsp lime juice, 1 tsp honey, 1/4 tsp red pepper flakes, and 1/4 tsp salt into a blender or food processor. Puree until smooth and slightly emulsified. Taste and adjust salt, acidity or honey as desired. Transfer to a small bowl or squeeze bottle and refrigerate until ready to use.

Prepare rolls

Split the Cuban rolls lengthwise, leaving a small hinge if you prefer. Butter the outside cut faces lightly with the softened butter (about 1/2 tbsp per side).

Layer ingredients

On the bottom half of each roll layer 2 slices of Swiss cheese, then a generous portion of pulled pork (about 1/3 cup per sandwich) distributed evenly, followed by 2 slices of thin-sliced ham and 2 slices more Swiss cheese. Top with a few thin lengthwise slices of dill pickle (about 2–3 per sandwich). Drizzle about 1 tablespoon of the cilantro-orange sauce over the pickles. Close the sandwich with the top half of the roll.

Grill the sandwiches

Heat a large skillet or griddle over medium heat. Place sandwiches seam-side down in the skillet and press gently with a heavy pan or sandwich press (or use a stovetop press). Cook 3–4 minutes per side until bread is golden and cheese is melted (total about 6–8 minutes). If using a pan without a press, weight the sandwich with a heavy skillet and cover loosely with a lid to help melt the cheese. Reduce heat slightly if bread browns too quickly.

Finish and serve

Remove sandwiches from the skillet, let rest 1 minute, then slice each sandwich in half. Drizzle any remaining cilantro-orange sauce over sandwiches or serve on the side. Serve immediately.

Taste one sandwich and add additional salt and black pepper if desired. Leftover pork can be refrigerated for up to 4 days; reheat gently with a splash of broth to keep moist.