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1. Preheat the oven to 350°. Roast the garlic: Cutting crosswise, slice off the top third of the garlic head and drizzle with 1 tablespoon of the olive oil. Season with ½ teaspoon of the salt and pepper and wrap loosely in aluminum foil. Place in the oven and bake until golden-brown and tender, about 45 minutes. Remove the garlic from the oven, set aside to cool slightly, then squeeze the garlic head over a small bowl to release the roasted cloves.
2. Roast the cauliflower: In a large, ovenproof skillet or cast-iron pan set over medium heat, add the bacon and cook, flipping each piece once, until both sides are browned and crisp, about 8 minutes total. Transfer the bacon to a paper-towel-lined plate and set aside for another use. Add the cauliflower quarters cut-side down to the bacon fat in the pan. Place the pan in the oven and cook until browned and a paring knife easily slides into the center of a wedge, about 50 minutes (if roasting a smaller head of cauliflower, it will take less time to roast).
3. Make the vinaigrette: In a medium bowl, whisk together the lime juice and the remaining 2 teaspoons of the salt until the salt dissolves. Whisk in the roasted garlic and fish sauce. Whisking constantly, drizzle in the remaining ¼ cup of the olive oil. Stir in the capers, parsley and chiles
4. To serve, place the cauliflower quarters on a platter and pour the vinaigrette over the top.
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