Bring pot of salted water to boil. Add in as many potatoes as you wish to make and cook until fork tender.
On a sheet pan, generously drizzle olive oil. Place tender potatoes on the cookie sheet leaving plenty of room between each potato.
With a potato masher, gently press down each potato until it slightly mashes, rotate the masher 90º and mash again. Brush the tops of each crushed potato generously with more olive oil.
Sprinkle potatoes with Kosher salt, fresh ground pepper, and fresh chopped rosemary (or chives, or thyme, or whatever herb you have available).
Bake in 450º oven for 20-25 minutes until golden brown.