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Step 1
Heat the oven to 450 degrees. Toss the cauliflower with the olive oil on a baking sheet. Season with salt and pepper, spread in an even layer and roast until browned and cooked through but retaining some bite, about 15 minutes.
Step 2
Transfer the cauliflower to an 8-inch or other 2-quart baking dish. (You could also bake this in individual ramekins; just mix the cauliflower with the other ingredients in a medium bowl before dividing.) Reserve 1/4 cup Cheddar. Add the remaining 1 1/4 cups Cheddar, heavy cream, garlic and cayenne to the cauliflower and stir to combine. Season with salt and pepper, then top with the reserved 1/4 cup Cheddar.
Step 3
Roast until the cream has thickened, the cheese has melted, and some of the cauliflower is browned on top, 15 to 20 minutes. Let sit 5 minutes before serving.