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Preheat the oven and baking sheet. Arrange a rack in the middle of the oven and add a large rimmed baking sheet to it; heat to 425°F.
Toss the halved potatoes with olive oil, kosher salt, and black pepper in a large bowl.
Remove the baking sheet from the oven and line with parchment paper. Spread the potatoes out on the baking sheet and nestle the sprigs of herbs and heads of garlic between them. Drizzle the garlic with olive oil, cover with foil, and roast for 30 minutes.
Uncover the baking sheet, stir the potatoes, and return them to the oven to roast until golden-brown and fork-tender, about 10 minutes.
When the potatoes are done, remove the sprigs then squeezed out a few cloves of garlic and gave everything a big stir.