Roasted Squash Ditalini with Crispy Guanciale

Snapshot

• Implements: sheet pan, large pot, skillet, mixing spoon, sharp knife, wooden spoon
• Oven setting: 425°F / 220°C for roasting squash
• Batch size: 6 main course servings or 8–10 as a side
• Pasta cooked separately for reliable texture

Ingredients

• 16 oz box ditalini (or small shells / elbows)
• ~1 lb butternut squash, peeled and cut into ½-inch cubes (fresh or frozen, see note)
• 2 Tbsp olive oil
• ½ tsp Diamond Crystal kosher salt (to start)
• 2–3 sprigs fresh thyme (or ½ tsp dried thyme)
• 8–12 fresh sage leaves or ½ tsp dried ground sage (if using dried, skip frying step below)
• ~7 oz guanciale, cut into small cubes (see rendering note)
• 2 cloves garlic, minced or grated
• 1 Tbsp tomato paste (for depth and color in the sauce)
• ¾ cup heavy cream
• ¾ cup whole-milk ricotta
• ½–¾ cup finely grated Parmesan or Pecorino Romano (divide in half: half for sauce, half for serving)
• Black pepper, to taste
• Optional: lemon zest or a small squeeze of lemon juice (for brightness at finish)
• Optional: 1–1½ cups frozen peas

Method

1. Roast the squash

   Preheat oven to 425°F. Toss the butternut squash cubes with olive oil, thyme, and the ½ tsp salt. Spread on a sheet pan in a single layer. Roast 20–28 minutes, stirring once halfway, until the edges begin to caramelize and the centers are soft.

   If using frozen cubed butternut squash: Roast straight from frozen. Increase oven temp to 450°F and cook 18–25 minutes, tossing once. Frozen squash releases more water, so it browns more slowly. Roast until any liquid evaporates and the edges pick up color. Texture will be slightly softer, which actually blends beautifully into the sauce.

2. Cook the pasta

   Bring a large pot of salted water to a boil. Add the full 16 oz of ditalini and boil until al dente. Reserve 1½ cups of pasta water (you’ll likely use about ½–1 cup), then drain the pasta.

3. Render the guanciale

   Place the cubed guanciale in a cold skillet and turn heat to low. Let it slowly render for 10–15 minutes until the fat melts out and the guanciale pieces are crisp. Pour off some of the rendered fat (reserve about 2–3 tablespoons in the pan for the sauce). Use a slotted spoon to transfer the crispy guanciale to a paper-towel lined plate and set aside for serving. Slow rendering gives the best texture and flavor (don’t rush it).

4. Fry the sage (if using fresh)

   Add the fresh sage leaves to the hot guanciale fat. Fry for 30–60 seconds until crisp, then remove and set aside. If using dried sage instead, skip this frying step and add the dried sage later with the sauce.

5. Build the sauce base

   Stir garlic and tomato paste into the guanciale fat. Cook 1–2 minutes until the garlic is fragrant and the tomato paste deepens in color.

6. Add squash and build texture

   Add the roasted squash to the pan. Lightly mash a portion of the cubes so the sauce becomes partly creamy, partly chunky.

7. Add cream, ricotta, cheese

   Pour in the heavy cream, then stir in ricotta and half of the grated Parmesan (or Romano). If using dried sage, add it here so it has a chance to bloom in the warm sauce. Stir until smooth and combined.

8. Adjust sauce consistency

   Add reserved pasta water a little at a time, stirring, until the sauce becomes saucy and glossy (enough to coat pasta but not pool). Usually ½–1 cup pasta water will do.

9. Combine pasta and sauce

   Add the cooked ditalini to the sauce and toss thoroughly. If using frozen peas, stir them in now and let them warm through for 2–3 minutes, just until bright green and tender. Taste now. Because guanciale, cheese, and pasta water already bring salt, you may only need a small pinch. Add black pepper generously. If the sauce tastes too rich or heavy, brighten with lemon zest or a splash of lemon juice.

10. Finish and serve

    Divide pasta among bowls. Top each portion with crispy guanciale, crisped sage leaves (if fresh), and a sprinkle of remaining Parmesan. Serve immediately.

Notes, swaps, and guardrails

Fresh vs frozen squash

If using frozen cubed butternut squash: there’s no need to thaw. Spread the frozen cubes on a sheet pan and roast at 450°F for about 18–25 minutes, tossing once halfway through. Frozen squash holds more water and browns more slowly, so the higher heat helps with caramelization. Watch for extra liquid on the pan. Roast until it evaporates and the edges begin to color. The texture will be a bit softer than fresh, which actually helps the sauce become creamy.

Guanciale rendering matters

Starting guanciale in a cold pan and rendering slowly over low heat brings out rich pork-cheek flavor and yields crisp, glassy bites. High heat risks overcooking or burning.

Herb options

If you don’t have fresh herbs, dried thyme and sage work, but dried sage can taste bitter if overheated. That’s why dried sage goes in with the sauce, while fresh sage gets a quick crisp fry for flavor and texture.

Salt carefully

Because guanciale, cheese, and pasta water all contribute salt, you want to start light. Taste after combining pasta and sauce and before seasoning again.

Brighten it up

A little lemon zest or a splash of lemon juice at the end cuts through the richness and brings freshness (especially nice if you lean heavy on cream and cheese).

Reheating leftovers

Leftover creamy pasta is a bit like a sleepy cat: it will cooperate again, but only if you coax it gently. The goal is to wake the sauce back up without breaking it or drying the squash.

Here’s the path that’ll make it taste almost like day one.

The best method (skillet + splashy rescue)

Render some fresh guanciale in a deep pan over medium low heat. Low and slow again, should take 15ish minutes. When crispy, scoop the guanciale onto a paper towel lined plate.

Slide the leftover pasta into your pan of pork fat and stir to combine. Add a splash of milk or cream to further loosen the sauce. (Max out at 2 tablespoons.)

The sauce will relax, rediscover its creaminess, and coat the pasta again. Add more liquid only if needed.

Let it warm slowly for 4–6 minutes, stirring occasionally. You don’t want anything to sizzle.

(If you don’t have fresh guanciale to crisp, double the cream/milk and warm it slightly in the pan before adding the leftover pasta.)

Add your freshly sauteed crispy guanciale at the end

Top each bowl with the freshly rendered crispy guanciale so it stays shatter-crisp instead of going soggy in the pan.

Optional but lovely

Brighten with:

• A tiny squeeze of lemon
• Fresh black pepper
• A sprinkle of parmesan

What not to do

Avoid the microwave unless you’re absolutely starving. It overheats in patches, makes the sauce grainy, and turns the squash to mush.

This recipe is adapted from Squash Ditalini Pasta with Crispy Pancetta by Gabriella Simonian at No Regretti Spaghetti.