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1
Start with your largest squash. Do not peel the skin of this one, as it is the outermost ring of your squashducken and the skin is vital for the structural integrity. Instead, use a very sharp knife to remove its hat (as if you were carving a jack-o'-lantern) and then scoop out its insides. As you work, I recommend you separate the inedible versus edible innards of your squash into two separate bowls: You'll probably be scooping away a lot of edible squash flesh that you can use later for roasting, soup, etc.
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2
Once you've emptied out the insides of the largest squash, you'll need to see what else needs to be done in order to get the next largest one to fit inside of it. You might need to slice off more of the squash near its top in order to make its bowl wider, or you might need to really go at the insides with a spoon to scrape away excess flesh. But don't panic if things seem like they'll be snug: You will be peeling the skin of the second-largest squash and whittling away its outsides. You can make it work!
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3
Oil the roasting pan, then set the hollowed, beheaded large squash inside of it. (I used our biggest Dutch oven, which cradled the squash nicely.)
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4
Now start on the second largest squash. Peel it, cut off its head, and scoop out the insides. You might need to whittle away at its flesh-thinning it out from both the inside and the outside will help ensure that it fits into the biggest squash. As you work, continue to judge whether your squash will fit inside its larger counterpart. BUT do be careful pressing it into the larger squash before you are certain-they can get stuck that way (it's happened to me).
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5
Repeat this beheading and bowl-ifying process with all of the squash, making to periodically gauge whether they are going to fit inside each other. Once that's done, congratulate yourself: The hardest part is over!
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6
Now you're ready to par-cook. Put the second biggest squash (remember: the largest squash does not need to be par-cooked) in a microwave-safe dish with a bit of water (1/8 to 1/4 inch is sufficient) on the bottom. Heat in the microwave in 5-minute increments until the squash is pliable; you should be able to wiggle it little without fear of breaking or tearing. The largest squash I microwaved took 8 to 10 minutes to reach this stage. Transfer the squash to a cooling rack while you microwave all of the other squash.
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7
PLANNING NOTE: You can (and I did) microwave one squash while carving the next one. But this could result in an issue. If you realize that the squash you've microwaved should have been thinned out further to fit the other squash, you might run into a major problem. So multitask, but with caution.
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8
Once all of your squash (except for that biggest one) have been microwaved, it's time to assemble. PASS GO AND COLLECT $200 i.e. scroll down and make pesto.
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9
Make the pesto: In a small pan over very low heat, warm all but 2 tablespoons of the olive oil, the sage, and the garlic just until the oil bubbles.
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10
Pour the oil into small bowl, fishing out the garlic cloves. Place the toasted hazelnuts in mini food processor along with the garlic cloves and process until a fine crumble. Add to the bowl of the sage and oil, then add the cheese and the remaining 2 tablespoons olive oil and stir to combine. Season to taste. This pesto is more nutty than herby or oily, so do not be alarmed in the mixture is dryer than you're used to.
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11
Preheat the oven to 350u00b0 F.
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12
Put the largest squash (the uncooked one) in the large, oiled roasting dish if you haven't already. Prick it all over its insides with a fork, then rub with olive oil. Sprinkle with salt, pepper, and paprika. Coat in a generous amount of the pesto (I used by hands for this task), then sprinkle with breadcrumbs and Parmesan.
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13
Rub the outside of the second largest squash with olive oil, then gently snuggle it into the largest squash. Continue with the oiling/seasoning/pesto-ing/breadcrumb-ing/chees-ing process until you've reached the innermost squash.
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14
Smear the rest of the pesto into any crevices, sprinkle with Parmesan, breadcrumbs, salt, pepper, and paprika. If you notice any moats or orifices, you can fill these spaces with cubed bread, which will absorb the delicious squash and pesto juices.
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15
Now you're ready to bake. Cover the roasting dish loosely with aluminum foil, then bake for 1 hour and 30 minutes. It will probably take need 2 hours total before the outer squash ring is cooked (make sure it's fork-tender and a texture you'll want to eat!), but I like to keep a close eye on it in the last 30 minutes.
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16
In the last 5 or 10 minutes, you can uncover the squash, sprinkle it with Parmesan and breadcrumbs, and get the top nice and toasty, if you'd like.
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17
Once the squashducken is finished, take it out of the oven and leave it alone until it's cool enough to handle. Then, get a friend to assist you! Get out your largest serving platter and position it near the pan. As one of you holds the pan and tilts it towards the platter, the other should assist with transferring the squashducken onto the platter. Let it cool until warm, then slice it into impressive wedges.
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18
Take a nap.
