Preheat oven to 375°F (190°C). This takes about 10 minutes. While oven heats, prepare a 9x13-inch baking dish.
Rinse 4 large bell peppers under cold water. Cut each pepper in half lengthwise from stem to bottom. Use a small knife to carefully remove the white seed membrane and all seeds from inside. Discard seeds and membranes.
Lightly brush the outside and inside of each pepper half with olive oil using a pastry brush or your fingers. This prevents sticking and helps them cook evenly. Arrange pepper halves cut-side up in the baking dish. Set aside.
Heat 1 tablespoon olive oil in a large skillet (12-inch) over medium-high heat for about 1-2 minutes until shimmering but not smoking.
Add 1 pound ground beef to the hot skillet, breaking it apart with a wooden spoon as it cooks. Stir occasionally for 5-7 minutes until beef is completely browned with no pink remaining. This is the key checkpoint—the meat should be crumbly and cooked through. Use a slotted spoon to transfer cooked beef to a clean bowl, leaving about 1 tablespoon of fat in the skillet.
Checkpoint: You are ready to move on when all the beef is brown and the pink is completely gone.
Add the remaining 1 tablespoon olive oil to the skillet. Add 1 diced medium onion and stir frequently for 3-4 minutes until the onion becomes soft and translucent (you should see through it). The onion will smell sweet and caramelized.
Add 3 minced garlic cloves and stir constantly for exactly 1 minute. You should smell a strong, pungent garlic aroma. This means the garlic is cooked and won't taste raw.
Checkpoint: You are ready to move on when the garlic is fragrant and the raw edge has cooked off.
Add 1 cup cauliflower rice to the skillet. Stir well to combine with the oil and aromatics. Cook for 2-3 minutes, stirring occasionally, until the cauliflower rice is slightly warmed through and begins to soften.
Return the cooked ground beef to the skillet. Stir to combine with the cauliflower rice mixture.
Add 1/2 cup softened cream cheese and 1/4 cup heavy cream to the skillet. Stir constantly for 2-3 minutes until the cream cheese melts completely and the mixture becomes smooth and creamy. The sauce should look like a thick, cohesive filling with no lumps.
Stir in 2 tablespoons tomato paste. Mix well for about 30 seconds so the tomato paste is fully incorporated and the filling turns a deeper color.
Add 1 teaspoon dried Italian seasoning, 1/2 teaspoon cumin, 1/2 teaspoon paprika, and 1/4 teaspoon cayenne pepper. Stir constantly for about 1 minute until all spices are evenly distributed. The filling should smell aromatic and complex.
Season with salt and black pepper to taste. Start with 1/2 teaspoon salt and 1/4 teaspoon pepper, stir, then taste a small spoonful. Add more if needed—the filling should taste savory and well-seasoned but not overly salty.
Remove the skillet from heat. Add 3/4 cup shredded cheddar cheese and stir until completely melted and combined. The filling should be creamy, smooth, and a light orange-yellow color from the cheese.
Checkpoint: You are ready to move on when the filling is smooth, creamy, and fully seasoned.
Carefully spoon the beef and cheese filling into each pepper half in the baking dish, dividing it evenly among all 8 pepper halves. Mound the filling gently but generously—it should reach close to the top of each pepper without overflowing.
Top each filled pepper half with the remaining 1/4 cup shredded cheddar cheese, dividing it equally. Sprinkle 2 tablespoons grated Parmesan cheese over the tops of all peppers.
Place the baking dish in the preheated 375°F oven on the middle rack. Bake for 20-25 minutes. Start checking at 20 minutes. The peppers are done when: (1) the pepper flesh is fork-tender when pierced with a knife, (2) the cheese on top is melted and beginning to turn golden brown at the edges, and (3) you see light browning on the corners of the cheese.
Checkpoint: You are ready to remove from the oven when the peppers are soft, the cheese is bubbling, and you see golden-brown spots on top.
Carefully remove the baking dish from the oven using oven mitts. Set on a heat-safe surface or trivet.
Let the peppers rest for 3-5 minutes before serving. This allows the cheese to set slightly and the filling to stabilize, making them easier to eat and less likely to fall apart.
Sprinkle fresh chopped parsley over the tops of the peppers just before serving. This adds color and a fresh herbal note. Serve immediately while hot, with pan drippings spooned over each pepper if desired.