Thievery is a big part of every Elder Scrolls game and The Elder Scrolls IV: Oblivion is no exception. A thief needs lockpicks, though, and Oblivion's tricky lockpicking mechanics mean that you're going to need a lot of them if you want to get your sticky fingers on the possessions of Cyrodiil's citizens.
This guide is valid for both Oblivion and Oblivion Remastered. Although the list of is actually pretty impressive, it didn't change the lockpicking minigame or Shady Sam's location.
How to Get Lockpicks in Oblivion
You can get lockpicks in two ways: buying and looting. If you want to buy lockpicks, then there are several vendors that specifically cater to shady clientele—more on those folks below. They'll be more than happy to sell you [[link]] a few lockpicks if you have gold. Normal vendors won't have lockpicks in their inventories, however, so you need to visit the right people.
If you don't want to buy lockpicks, you can usually loot them from bandits and goblins while traveling between settlements. Dungeons and caves in particular are great sources of lockpicks which you'll usually find in chests at the end of a dungeon crawl or on the bodies [[link]] of bandits you've killed. The chests in bandit hideouts tend to have a few, too.
Where to buy lockpicks in Oblivion
If you need lockpicks, there's only one man who can help you early in the game. Shady Sam is a merchant outside of the Imperial City walls who deals in shady supplies including lockpicks. You [[link]] can find him along the northwestern edge of the city walls between the Talos Plaza District and Elven Gardens District gates.
Shady Sam carries 30 lockpicks at a time and his stock refreshes daily if you buy them all, making him the best place to get lockpicks early in Oblivion.
If you want to gain access to more lockpick vendors in Oblivion, you need to join either the Thieves' Guild or the Dark Brotherhood. The former is the better choice since there's not as high of an entry cost—no murder hazing ritual—and the guild's fences have huge supplies of lockpicks for sale. Dark Brotherhood merchants don't carry as many, but they still have enough for aspiring thieves to buy.
You can quickly join the Thieves Guild by getting thrown in jail for a nonviolent crime like theft or pickpocketing or read wanted posters throughout the Imperial City and then ask beggars for more information about the guild. Or you could join the Dark Brotherhood by killing an innocent NPC and awaiting a visit from a representative of the Dark Brotherhood.
How Lockpicking Works in Oblivion
Oblivion's lockpicking minigame is very different from the one Bethesda started using in Fallout 3 and Skyrim. Once you get the hang of it, it's pretty straightforward though.
To open a lock, you have to use the lockpick to set every tumbler at the top of the lock. You move the lockpick by moving your mouse upward to nudge the tumblers and then clicking when the tumbler reaches the top of its slot. The tumblers move at varying speeds and the timing is tricky, so it takes some getting used to. If you mess up, your lockpick will break and some of the already set tumblers will reset to their original positions.
Sometimes the tumblers will move upward more slowly when you nudge them with the lockpick. That's the best time to try and set them in place. If you try to click when they're moving too fast, you run the risk of breaking your lockpick. You should also listen closely while lockpicking. Tumblers move more slowly when they're easiest to set and they'll also make a slightly different noise when you nudge them.
It's a tricky system that definitely takes some getting used to, but you can easily pick locks that are way above your skill level if you really get good at it. Improving your Security skill will make things a lot easier, but you can still pick even the hardest locks if you get the timing down.