Preheat the oven to 400°F (200°C) or 160°C if using a fan oven.
Using a sharp knife, cut each acorn squash in half. Avoid cutting through the tough stem but rather slice around it.
Scoop out the seeds and stringy bits using a spoon or an ice cream scoop. Discard the seeds or save them to roast later.
Place the squash halves cut side up on a sheet pan or a roaster.
Drizzle the olive oil generously over the cut sides of the squash.
Season with the salt, black pepper, Italian seasoning, and cayenne powder.
Roast uncovered in the oven for 30 to 40 minutes, or until fork-tender.
Once roasted, remove the squash from the oven and allow it to cool until it’s safe to handle.
Carefully scoop out the tender flesh to use in recipes or serve the halves directly.
