Adjust rack to middle position and preheat oven to 400 degrees. Bring a large pot of salted water to a boil. Wash and dry produce.

Cut each tomato into 6 wedges. Place whole garlic clove in a small piece of aluminum foil and drizzle with olive oil, salt, and pepper; cinch into a packet.

Drizzle a foil-lined baking sheet with oil, then place tomato wedges on it skin side down. Coat with a drizzle of olive oil, 1 tsp Tuscan Heat Spice (2 tsp for 4 servings) (you’ll use more Tuscan Heat Spice later), salt, and pepper. Place garlic pouch next to tomatoes. Roast on middle rack until tomatoes are just wilted, 20-25 minutes.

Heat a medium dry pan over medium-high heat. Add bacon*; cook, turning occasionally and adjusting heat if browning too quickly, until crispy, 6-10 minutes. Turn off heat; transfer to a paper-towel-lined plate. Wipe out pan. Once cool enough to handle, roughly chop.

Once water is boiling, add linguine to pot. Cook, stirring occasionally, until al dente, 9-11 minutes. Reserve ¾ cup pasta cooking water (1½ cups for 4 servings), then drain. Keep empty pot handy for Step 5.

While linguine cooks, pat chicken* dry with paper towels. Season both sides with 1 tsp Tuscan Heat Spice (2 tsp for 4 servings), salt, and pepper.

Heat a large drizzle of olive oil in pan used for bacon over medium-high heat. Cook chicken until browned and cooked through, 5-7 minutes per side. Turn off heat; cover to keep warm. TIP: If you don’t have a lid, you can tent loosely with aluminum foil.

Once garlic is done roasting, carefully remove from pouch. Melt 1 TBSP butter in pot used for pasta over medium heat. Add 1 tsp Tuscan Heat Spice and roasted garlic; mash with the back of a spoon. 

Stir in ⅔ cup reserved pasta cooking water, cream cheese, half the Parmesan (save the rest for garnish), and 2 TBSP butter (1 cup pasta cooking water and 3 TBSP butter for 4 servings), until smooth. Turn off heat; season with salt and pepper.

Add linguine to pot with sauce; toss until pasta is evenly coated. (TIP: If necessary, stir in more pasta cooking water a splash at a time until everything is coated in a creamy sauce.) Season with salt and pepper.

Slice chicken and serve on top of linguine alongside roasted tomatoes. Garnish with bacon and remaining Parmesan. Serve.