Rinse fingerling potatoes and place them in a large pot covered with water. Bring water to a boil and cook until potatoes are very tender, about 20 to 25 minutes.
Drain potatoes in a colander and let them cool and dry out. Using the palm of your hand, press the potatoes until lightly smashed.
Heat 2 tablespoon olive oil in a cast iron pan over medium heat. Place one layer (about half the potatoes) in the pan. Sprinkle salt, pepper, and Italian seasoning over potatoes and allow potatoes to brown.
After about 5 to 7 minutes, flip over potatoes and sprinkle more salt, pepper, and Italian seasoning on them. Let it brown for another 5 to 7 minutes. Remove and place on a plate. Repeat with the other half of the potatoes.
When done, do not remove potatoes from pan but return the earlier half portion back to the pan. Sprinkle minced garlic over potatoes. Stir to get potatoes well mixed with garlic, about 1 to 2 minutes.
Turn off heat and transfer to serving dish.