Oblivion Remastered: How to Max Sneak Skill Fast (Exploit Guide)

Want to max out Sneak fast in Oblivion Remastered? Here’s how to use a simple exploit at the Imperial City Prison to level up your Sneak skill easily without getting caught.
Oblivion Remastered: How to Max Sneak Skill Fast (Exploit Guide)
In The Elder Scrolls IV: Oblivion Remastered, Sneak might be a minor skill, but it’s a major game-changer—especially for players who love pickpocketing or sneaking up on enemies without being spotted. It’s super important for missions in the Thieves Guild and Dark Brotherhood, so getting it leveled up early is a huge win.
Problem is, leveling Sneak the normal way can be slow and risky. Pickpocketing in public can easily get you slapped with a fine or thrown in jail by a guard. Luckily, there’s a simple exploit you can use to max out your Sneak without any trouble. Here’s exactly how it works.
How to Do the Max Sneak Skill Exploit in Oblivion Remastered
First thing you want to do is fast travel back to the Imperial City Prison—the same place you broke out of during the tutorial.
- Head inside the Bastion, and right away, you’ll spot an Imperial Jailor sitting nearby.
- Talk to the Jailor. Unlike regular guards, he gives you a special option: “Visit a Prisoner.”
- Choose that option. He’ll tell you he’ll open the door for you, but that he’s supposed to accompany you inside.

Now here’s the trick:
- As he opens the wooden door, step just slightly inside, but make sure the Jailor stays outside.
- Talk to him again immediately and pick “Visit a Prisoner” one more time.
- He’ll repeat the dialogue and close the door behind you, locking you alone inside the prison cells.
Perfect. You’re free to move without being watched.
Leveling Sneak at Claudius Arcadia’s Cell
- Head downstairs until you find Claudius Arcadia’s cell.
- Crouch nearby, and you’ll see the option to Pickpocket him—even though he’s got nothing on him.
- Important: It doesn’t matter that he’s empty-handed. The pickpocket animation alone is enough to give you Sneak XP.
Just keep repeating the pickpocket action over and over again. You’ll see your Sneak skill rising steadily.

Things to Keep In Mind
- Every pickpocket attempt grants the same amount of XP, whether you succeed or fail, or whether the target has items or not.
- After you hit around Sneak Level 50, the XP gain will start to slow down. Totally normal—just keep grinding if you’re aiming for that maxed-out Sneak.
- You won’t get caught doing this because there are no guards or witnesses around.
If you’re patient enough, you can easily hit Sneak Level 100 using this method. No bounty, no fines, no jail time. Just smooth, stealthy leveling.
Sneak is one of those underrated skills that can absolutely carry you through a stealthy playthrough of Oblivion Remastered. Whether you’re pickpocketing nobles or silently taking down targets, this exploit makes getting there way faster—and honestly, a lot less stressful.
So grab your Thieves Guild armor, crouch low, and get to work! 🕵️♂️✨
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