Pickpocketing in Skyrim is an exciting and rewarding skill, allowing you to acquire wealth, rare items, and a tactical edge in combat. This step-by-step guide will help you efficiently build and level your Pickpocket skill to 100.

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Step 1: Activate the Thief Stone

Start by visiting the Guardian Stones and choosing the Thief Stone. This grants a 20% boost to Pickpocket skill progression, speeding up your leveling journey from the very beginning.

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Step 2: Craft or Obtain the Right Gear

Enchanted Armor (Optional)

While not required, you can create a powerful pickpocketing set using Enchanting Level 100. For each of the four gear slots—gloves, boots, necklace, and ring—enchant the following:

• +40% Pickpocketing Success
• +40% Sneak

Blackguard Armor Set

A faster alternative is the Blackguard Armor Set, found in Raven Rock (Dragonborn DLC). The boots alone provide a 40% boost to pickpocketing.

How to Obtain It:

1. Wait until 9:30 PM for the blacksmith to leave his shop.
2. Use Whirlwind Sprint to bypass locked doors if needed.
3. Enter stealthily and loot the armor without incurring a bounty.

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Step 3: Use Support Spells

Two Illusion spells significantly increase your stealth capabilities:

• Muffle – Helps level up Illusion and quiets your movement.
• Invisibility – Makes you undetectable. Requires Illusion Level 75 and is available from Drevis Neloren at the College of Winterhold.

Use both together for maximum stealth while pickpocketing.

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Step 4: Train Efficiently

Mirabelle Keep Jail Exploit

1. Go to the jail near Mirabelle Keep.
2. Bribe the guard to avoid punishment.
3. Repeatedly pickpocket a prisoner. Place 300–600 gold in their inventory to use for practice.
4. Use quick-save/load to retry failed attempts.

Suggested Gold Amounts:

• Level 15–50: 300 gold per attempt
• Level 50–70: 900 gold per attempt
• Level 70+: Combine with trainers for faster progression

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Step 5: Use Trainers

Increase your skill more efficiently with expert-level trainers:

• Expert Trainer (70–75): Located in Windhelm, near the blacksmith or cemetery. Training costs ~11,000 gold.
• Master Trainer (85–90): Found in Riften inside the Thieves Guild. Training costs ~22,000 gold.

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Step 6: Power Level to 100 with the Black Book

1. Travel to Raven Rock Mine and complete the quest to obtain a Black Book.
2. Choose the Scholar’s Insight ability, which grants 2 skill points per skill book.

Pickpocket Skill Book Locations:

1. Riften Ratway – On a table in the Ragged Flagon
2. Honorhall Orphanage (Riften) – Between a bed and nightstand
3. Windhelm Docks – Inside the Argonian Assemblage
4. Mara’s Eye Pond – Beneath a tree stump via a trap door
5. Morthal – Hidden under a basket in a house

Reading all five books gives 10 levels when combined with Scholar’s Insight—ideal for jumping from Level 90 to 100.

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Step 7: Recommended Perks

Invest your perk points in the following to become a master thief:

• Light Fingers – Improves pickpocket chance
• Night Thief – +25% success on sleeping targets
• Extra Pockets – +100 carrying capacity
• Cutpurse – Makes stealing gold easier
• Keymaster – Guaranteed key theft
• Misdirection – Steal equipped weapons
• Perfect Touch – Steal worn armor and items

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Conclusion

With the right gear, spells, and training methods, you can efficiently level Pickpocketing to 100 and unlock powerful gameplay advantages. Use quick-saves wisely, stack enchantments, and enjoy living life as Skyrim’s ultimate master thief.

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