I start by slicing the top off my pumpkin like a lid and scooping out all the seeds and stringy bits with a spoon. I brush the inside with olive oil, then pop it onto a baking sheet and roast it at 400°F for about 20 minutes. Once it's out, I pat the inside dry with a paper towel so it doesn't get watery later.
While the pumpkin roasts, I whisk together honey, chipotle powder, crushed red pepper, a pinch of cinnamon, and a pinch of salt in a small bowl. This only takes a minute, but it's the flavor backbone of the whole dish. I always taste it here and adjust the heat level to my mood that day.
Once the pumpkin has cooled enough to handle, I spoon a little hot honey into the bottom, nestle the brie wheel inside, and score the top in a crisscross pattern. Then I drizzle more honey over the cheese, saving a bit for later. I cover it with the pumpkin lid and bake at 400°F for 10 minutes, then remove the lid and bake for another 15 minutes until the brie is soft and jiggly.
I pull the pumpkin out once the brie looks ready to collapse at the slightest touch. I drizzle the reserved hot honey over the top, scatter on some fresh chives, and let it sit for a minute or two before digging in with crackers or crusty bread.