Heat the oven. Set to 400°F (200°C). Line a baking sheet with parchment for easy cleanup.

Prep the squash. Halve the spaghetti squash lengthwise and scoop out the seeds. Rub the cut sides with olive oil and season generously with salt and pepper. Place cut-side down on the baking sheet.

Roast until tender. Bake for 35–45 minutes, depending on size. The squash is done when the strands pull away easily with a fork and the edges have a light golden color.

Brown the beef. While the squash roasts, heat a large skillet over medium-high heat. Add a drizzle of oil, then the ground beef. Cook, breaking it up, until browned and no longer pink, about 5–7 minutes. Drain excess fat if needed.

Add aromatics. Stir in the diced onion and cook 3–4 minutes until softened. Add the garlic and cook 30 seconds, just until fragrant.

Build the sauce. Stir in ketchup, mustard, Worcestershire, smoked paprika, 1/2 teaspoon salt, and a few grinds of pepper. Simmer 2–3 minutes to thicken slightly. Taste and adjust seasoning. Fold in the chopped pickles for that classic burger tang.

Shred the squash. Flip the roasted squash halves cut-side up. Use a fork to scrape and fluff the strands, keeping them in the shell to form bowls.

Fill and cheese. Divide the beef mixture between the squash halves. Toss gently with the squash strands so everything mingles. Top with shredded cheddar, pressing lightly so it sticks.

Melt and finish. Return to the oven for 5–8 minutes, until the cheese is fully melted and bubbling at the edges. For extra color, broil 1–2 minutes, watching closely.

Top and serve. Add optional toppings like shredded lettuce, diced tomato, sesame seeds, or more pickles. Serve hot, straight from the “boats.”