No matter what play style you like to use in Skyrim, chances are you'll do a bit of stealing on the side. The game's collection of Thief skills is incredibly versatile, providing players with easy ways to resolve conflict or get rich quickly. Of these skills, Pickpocket is one of the most useful in the game, making it ideal for players to quickly level up early on.

Though Pickpocketing may initially be difficult to power level, there are plenty of tricks to get yourself to a skill level of 100. Here you'll find our guide to quickly leveling up your Pickpocket skill to give yourself an edge in the early game.

How Leveling Pickpocket Works

Unlike previous Elder Scrolls games, Skyrim's leveling system is entirely dependent on how much a player uses a skill. So, the more you successfully pickpocket NPCs, the faster your Pickpocket skill will level up. Luckily, you'll get a clear indication of how successful each pickpocket attempt will be through corresponding percentages. The higher the percentage, the more likely it is that your attempt will succeed. While it may be tempting to go for the easy steals, keep in mind that the more difficult attempts will give you more experience.

Though it's important to remember that there will always be a chance for failure. 99% chance may be close, but it isn't 100%!

Skyrim Power Level Pickpocket

Of course, you could always go around Skyrim's various towns and try to pickpocket anyone you come across, but there are certainly easier ways to power level this skill. Pickpocketing Septims from NPCs will always net you some experience, but the real strategy focuses on higher-value items. The higher value the item you're stealing, the more experience you'll gain from taking it. Items like gems and jewelry that are high value but lightweight will be easy targets - and you'll make a nice profit selling them to a fence.

It'd be a good idea to get some basic practice pickpocketing gems from sleeping NPCs, as you'll be less likely to be spotted by a guard. As you might expect, the pickpocket attempt will always fail if someone sees you. It doesn't have to be your target; prying eyes will alert nearby guards.

Easiest Ways to Power Level Pickpocketing - Skill Trainers

By far the easiest way to quickly max out your pickpocket skills is to find a Pickpocket trainer. These NPCs will help you increase your proficiency in certain skills a maximum of five times, letting you quickly level up for a fee. When it comes to Pickpocket trainers, there are two you should visit: Expert Silda the Unseen and Master Vipir the Fleet. Silda can be found outside the Candlehearth Hall in Windhelm and Vipir in The Ragged Flagon in Riften. You'll have to be a member of the Thieves Guild to train with Vipir, but that questline will conveniently set you on the path to becoming an expert Pickpocket as well.

Skyrim Power Level Pickpocket

Silda the Unseen

The best thing about skill trainers is that their pockets are now conveniently full of gold coins ready for pickpocketing! Steal your money right back to gain even more experience and fill your purse right back up.

One major thing to keep in mind is that you can't pickpocket more than 999 Septims from an NPC. Any attempt will automatically fail, causing the NPC to immediately attack you or call for guards to arrest you. While this cap limits how much you can steal back from your trainer, you'll have leveled up enough to successfully take your coins back from any other trainers you learn from.

Other Exploits And Tricks To Power Level Pickpocketing

Alright, if you really want to go for that 1000+ Septim purse, you can immobilize the NPC beforehand. A quick Unrelenting Force shout or Paralysis spell will do the trick. However, if the guards catch you, you'll have to pay a pretty fine to get off scot-free, making your pickpocket attempts moot. You can always quicksave before a risky Pickpocket attempt as a safety net!

A safer option would be to take advantage of the Strange Amulet exploit. Once you gain the Strange Amulet item from the Blood on the Ice quest, you'll be able to sell it to Calixto Corrium. The Windhelm shopkeeper will buy it for a cool 500 Septims. Even better? You can repeatedly steal the item back and immediately re-sell it to him. Not only will you increase your Pickpocket skill, but you'll also earn a sweet sum of Septims to boot.

And that covers our guide to Power Leveling Pickpocketing in Skyrim! If you're looking to Power Level other skills, be sure to check back here for more tips and tricks on quickly becoming the strongest Dragonborn possible.