Start by preheating the oven to 400F.
Cut cut the top of the garlic head off, so the cloves are exposed. Drizzle with olive oil and wrap in foil. Place the wrapped garlic head in a baking dish and bake for 40-60 minutes, until golden and soft.
Meanwhile, peel and cut each potato into chunks. Place the potato chunks in cold water and bring them to a boil. Boil for 15-30 minutes, until a fork easily pierces them.
Strain the potatoes, reserving some of the potato water (around 1 c)
Mash the potatoes. Add in some of the reserved potato water until the potatoes are nice and creamy. Adjust as needed.
Remove the garlic from the oven and let it cool before squeezing the roasted gloves into the mashed potatoes. Mash everything together.
Fold in the salt and vegan butter and non-dairy milk (if using.)
Fold in the chopped herbs and season with more salt to taste.