You can get lockpicks in Oblivion through several methods:
- Buying from Shady Sam: He is the easiest and most reliable vendor for lockpicks early in the game. Shady Sam is located outside the Imperial City walls near the Chestnut Handy Stables, northwest of the city. He sells lockpicks at 6 gold each, with a daily stock of up to 30 lockpicks that refreshes every day
- Joining the Thieves Guild: Once you join the Thieves Guild, you can buy lockpicks from fences who have a large, regularly restocked supply (up to 100 lockpicks). The first fence you meet is Ongar the World-Weary, located in Bruma’s southwest corner. He sells lockpicks at about 6 gold each
- Looting from enemies and dungeons: Bandits, goblins, and their hideouts are great sources of lockpicks. You will often find lockpicks on bandit bodies or in chests within caves and dungeons
- Dark Brotherhood merchants: If you join the Dark Brotherhood, their merchants also sell lockpicks, though in smaller quantities compared to the Thieves Guild fences
- Quest reward - Skeleton Key: At level 10, you can start the Nocturnal Daedric Shrine quest, which rewards you with the Skeleton Key, an unbreakable lockpick that boosts your Security skill by 40, making lockpicking much easier
In summary, the best places to get lockpicks are buying from Shady Sam outside the Imperial City, purchasing from Thieves Guild fences after joining the guild, and looting bandit or goblin camps and dungeons. For a permanent solution, completing the Nocturnal quest for the Skeleton Key is highly recommended.
