Preheat the oven to 450°F. Fill a medium pot (or large for 4 servings) 3/4 of the way up with salted water; cover and heat to boiling on high. Wash and dry the fresh produce. Cut off and discard the ends of the squash. Halve lengthwise; using a spoon, scoop out and discard the pulp and seeds, then cut crosswise into 1/2-inch pieces. Transfer to a sheet pan. Drizzle with olive oil; season with salt and pepper. Toss to coat. Arrange in an even layer. Roast 18 to 22 minutes, or until browned and tender when pierced with a fork. Remove from the oven.

Meanwhile, thinly slice the mushrooms. Halve, peel, and thinly slice the shallot(s). Thinly slice the chives. Roughly chop the pistachios.

Add the ravioli to the pot of boiling water. Cook, stirring occasionally, 3 to 5 minutes, or until the ravioli float to the top of the pot. Turn off the heat. Reserving 1/2 cup of the ravioli cooking water (or 1 cup for 4 servings), drain thoroughly and return to the pot.

Meanwhile, in a medium nonstick pan (or large for 4 servings), heat a drizzle of olive oil on medium-high until hot. Add the pancetta. Cook, stirring occasionally, 4 to 5 minutes, or until lightly browned and cooked through. Leaving any browned bits (or fond) in the pan, transfer to a paper towel-lined plate.  

In the pan of reserved fond, heat a drizzle of olive oil on medium-high until hot. Add the sliced mushrooms and sliced shallot(s); season with salt and pepper. Cook, stirring occasionally, 3 to 4 minutes, or until softened. Add the béchamel (carefully, as the liquid may splatter), mushroom duxelles, cream (shaking the packet before opening), half the parmesan, and as much of the truffle zest as you'd like; season with salt and pepper. Cook, stirring constantly, 30 seconds to 1 minute, or until combined. Turn off the heat.

To the pot of cooked ravioli, add the spinach, sauce, and half the reserved ravioli cooking water; season with salt and pepper. Cook on medium-high, stirring frequently, 1 to 2 minutes, or until the spinach is wilted and the ravioli are thoroughly coated (if necessary, gradually add the remaining cooking water to ensure the ravioli are thoroughly coated). Turn off the heat.

In a large bowl, whisk together the vinegar and 1 tablespoon of olive oil (or 2 tablespoons for 4 servings); season with salt and pepper. Add the arugula and roasted squash; toss to coat. Serve the finished ravioli with the salad on the side. Top the ravioli with the cooked pancetta, remaining parmesan, and sliced chives. Garnish the salad with the chopped pistachios, cherries, and goat cheese (crumbling before adding). Enjoy!