Oblivion Remastered: How to Pickpocket Without Getting Caught

Want to become a master thief in Oblivion Remastered? Here’s everything you need to know about how pickpocketing works, success tips, and what happens if you get caught.
How to Pickpocket in Oblivion Remastered
Steal Smart. Walk Free.
In The Elder Scrolls IV: Oblivion Remastered, there’s no one telling you how to behave—you’re free to be the hero, a chaotic villain, or, if you prefer, a sneaky kleptomaniac. Pickpocketing is one of the more entertaining crimes in Cyrodiil, but it’s not as simple as crouch, click, and profit. There’s a method to the madness.
Here’s your guide to becoming a successful pickpocket in Oblivion Remastered without getting locked up.
🕵️ How Pickpocketing Works
The system in the remastered version sticks pretty closely to the original. To pickpocket:
- Crouch (Sneak mode): Hit your sneak button and approach your target quietly.
- Interact with the NPC: This opens their inventory for you to browse.
- Grab the Goods: Choose what to swipe—carefully.
The catch? If you’re spotted while trying to steal something, or you get too greedy, the attempt will fail, and you’ll face the consequences.

🧠 What Affects Pickpocketing Success?
Success isn’t random—several things influence your odds:
- Sneak Skill: The higher, the better. Level it up for more silent success.
- Item Value: Expensive items are harder to steal unnoticed.
- Item Quantity: Stealing a single apple? Easy. Grabbing five? Risky.
Basically, the more subtle your theft, the better the odds.
💀 What Happens If You Fail?
Failing a pickpocket attempt can spiral fast:
- 🕛 No Second Try Until Tomorrow: If you mess up, you can’t try again on the same NPC until after midnight.
- 😡 Disposition Drops: Most NPCs will instantly like you way less (25+ points gone), and might even turn hostile if they already disliked you.
- 🚨 Guards Will Come For You: You’ll get a bounty, and the guards won’t hesitate to chase you down and demand justice (or gold).
🧙♂️ Pro Tip: Use the Chameleon Effect
If you want to boost your stealth game, grab gear or spells with the Chameleon effect. It reduces the chance of detection, making it a lot easier to snatch items without anyone noticing.
The higher your Chameleon percentage, the more invisible you are—even while moving.
Pickpocketing in Oblivion Remastered is risky, but super rewarding once you get the hang of it. Focus on building your Sneak skill, pick your targets wisely, and don’t get greedy. Oh—and if you get caught, make sure you’ve got some coin for bail or a good set of legs to run.
Stay sneaky out there.
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- How to Get the Fin Gleam Helm Early in Oblivion Remastered
- How to Kill Will-o-the-Wisps in Oblivion Remastered
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