You can get lockpicks in Oblivion from several sources:
- Buy from Shady Sam : He is a merchant located outside the Imperial City walls near the Elven Gardens district. He sells lockpicks for 6 gold each and you can buy up to 30 lockpicks daily. His inventory refreshes, so you can repeatedly purchase from him
- Join the Thieves Guild : Once you join, you can buy lockpicks from fences such as Ongar the World-Weary in Bruma. These fences have a large, regularly restocked supply of lockpicks (around 100 each) available at a cheap price. This is considered the best long-term source for lockpicks
- Loot from enemies and dungeons : Lockpicks can be found by looting bandits, goblins, and chests in dungeons or caves. Goblin mines and bandit hideouts are especially good places to find lockpicks as loot
- Dark Brotherhood merchants : They also sell lockpicks, but in smaller quantities compared to the Thieves Guild fences
Additionally, completing the Nocturnal Daedric Shrine quest rewards you with the Skeleton Key, an unbreakable lockpick that greatly boosts your Security skill, reducing the need to buy or find lockpicks
. In summary, the easiest and most reliable ways to get lockpicks are buying from Shady Sam early on and joining the Thieves Guild to access fences with large stocks of lockpicks. Looting enemies and dungeons supplements your supply naturally throughout the game
