How To Level Up Pickpocket In Skyrim

Become a Sticky-Fingered Superstar in Skyrim!

Alright, adventurer! You wanna be the ultimate sneak thief? The kind of person who can liberate a dragon priest's mask right off his face while he's mid-roar? Let's get you there!

Step 1: Find a (Willing!) Victim

First, you need someone to practice on. Forget dragons for now. Think less "fire-breathing lizard" and more "sleepy shopkeeper".

Whiterun is your best bet. Everyone there is a little too trusting (bless their hearts!).

Step 2: The Art of the Sneak

This is key: you need to be as quiet as a butterfly farting on cotton. Hit that sneak button (usually Ctrl).

See that eye icon? If it's fully open, you're busted! If it's closed, you're golden!

Stay in the shadows like a grumpy teenager avoiding chores.

Step 3: Pocket Emptying 101

Now comes the fun part! Get behind your target, open their pockets, and prepare to be amazed (or caught, which is also a learning experience!).

Don't get greedy at the start. Start with the small stuff, like potions or cheap rings. Think of it as petty larceny practice.

The higher the value and the weight of the item, the lower your chances of success, so start low and build your way up.

Step 4: Leveling Up Faster Than You Can Say "Hold!"

Okay, here’s the real secret sauce. The Train & Pickpocket method! Find a trainer, specifically a Pickpocket trainer like Silda the Unseen in Windhelm or Vipir the Fleet in Riften.

Pay them to train you in Pickpocket. Then... pickpocket the gold back! It's a win-win (for you, at least).

Repeat this process until you're richer than Titus Mede II himself (and probably better at sneaking).

Step 5: The Perks of Being a Pickpocket

As you level up, you'll unlock sweet perks. "Light Fingers" increases your pickpocketing chance. "Night Thief" makes you even harder to detect when sneaking.

My personal favorite? "Poisoned." Lets you slip poison into people's pockets. Imagine the look on their faces... eventually.

Consider "Misdirection", which allows you to pickpocket equipped weapons. And "Perfect Touch" which lets you pickpocket equipped items AND gold!

Step 6: Gear Up for Grand Larceny

Enchantments are your friend! Find gear (gloves, rings, necklaces) that boost your Pickpocket skill.

Think of it as your sticky-fingered uniform. Soon you'll be able to strip the armor off a guard without him even noticing!

Step 7: Avoiding Sticky Situations (Pun Intended!)

Getting caught sucks. Guards have no sense of humor. Save often, especially before attempting a risky pick.

If you *do* get caught, try to sweet-talk your way out of it. Bribes, persuasion... whatever it takes!

Sometimes running away and paying the fine is the best option, depending on the price of your bounty.

Step 8: The Final Exam: Dragons!

Okay, maybe not *dragons* yet. But practice on tougher targets. Rich merchants, powerful mages, grumpy Jarls.

Challenge yourself! See if you can lift the Skeleton Key from Mercer Frey. Or maybe just steal all the sweetrolls from the kitchen in Dragonsreach.

Step 9: Bask in Your Thieving Glory

Congratulations, you're now a master pickpocket! You can relieve anyone of their valuables without them batting an eye.

Use your newfound skills for good (or evil, I'm not judging). Just remember: with great pickpocketing skill comes great responsibility... to be sneaky!

Go forth and pilfer! May your pockets be ever full, and your crimes go unnoticed!