Skyrim Pickpocket Guide
Master the Art of Robbing them Blind
by Leto Kersten
Pickpocketing, or the "art" of stealing the precious belongings of someone else for your character's gain. This skill is excellent for working your way up the economical food chain of Skyrim. It will also prepare you for Thieves Guild jobs. That use of pickpocket is sinister, but there are positive reasons to work on this skill as well. Read on to learn more.
Benefits of Training Pickpocketing
Upon first sight this skill may only exist for being an easy money maker. While it certainly will, there are some perks in this tree that are practical for every other build in Skyrim if you are willing to spend time, perks and perhaps some money.
The perk Extra Pocket is incredibly practical because it provides your character with 100 more carry weight on top of their standard 300 you begin with. It will only cost you 3 perk points and level 50 in the Pickpocket skill. If you want this perk but you are roleplaying a character that doesn;t steal, you can go to Windhelm from time to time and pay Silda the Unseen a visit. She is an Expert Pickpocket trainer and can easily train you all the way up to level 50 without your character having to steal anything. By training with her up to five times each level, you can get this perk with a count of 0 stolen items in your journal. Know if you're playing a character that doesn't steal, there are a lot of quests you cannot complete. Followers stealing for you will count as a stolen item in your character's journal as well.
Raising the Pickpocket Skill
Stealing items from NPCs will raise Pickpocketing.The more valuable the item, the lower the chance of success, but you will get more skill experience the more valuable it is. The aforementioned Expert trainer Silda the Unseen in Windhelm can help you raise this skill, and if you join the Thieves' Guild you'll be able to train with Viper, who is a Master Pockpocket.
Skyrim Pickpocket Skill Perks
It takes 12 points to max out Pickpocketing, but it's unlikely many builds will need them all. You can still get some great perks with minimal investment however. For example, to benefit from the Extra Pocket perk you only need to invest three perk points.
Light Fingers (5 Ranks, 20/40/60/80/100% Pickpocket Bonus)
(level 0/20/40/60/80 Pickpocket Skill required)
Pickpocketing bonus of 20% per rank. Item weight and value reduce pickpocketing odds. You only need to invest one point in this as a prerequisite. When you are level 100 and you have more of the perks in this tree the chance of failing is pretty low. The chance of success is capped at 90%.. I can't come up with any build who needs points in this. It would help early on, but later the points would be wasted. In Skyrim, one can become very rich pretty easily and this tree seems to exist to improve your carry weight, poison NPCs, and to collect/upgrade NPC armor.
Night Thief
(level 30 Pickpocket Skill required)
+25% Change to pickpocket if the target is asleep. This perk is okay, but you will mainly want to invest in it to benefit from later perks.
Poisoned
(level 40 Pickpocket Skill required)
Silently harm enemies by placing poison in their pockets. If you want something new in your game, you could go with this. See the Witch part of this guide below.
Extra Pockets
(level 50 Pickpocket Skill required)
Carrying capacity is increased by 100. Arguably one of the best perks in this tree. It does exactly what the description says and is very helpful to your ability to make money and carry more equipment.
Cutpurse
(level 40 Pickpocket Skill required)
Pickpocketing gold is 50% easier. High quantities of gold can be the hardest items to pickpocket, so this may help you score some serious coin.
Keymaster
(level 60 Pickpocket Skill required)
Pickpocketing keys almost always works. If you save before trying to pickpocket a key and fail, you can always reload. Therefore, I don't see any reason to pick this perk.
Misdirection
(level 70 Pickpocket Skill required)
Can pickpocket equipped weapons. Steal their weapon then kill them, or simply keep it for profit or your own use. You can steal a guards' weapons, enchant them and give them back. You can give them any weapon, but taking theirs is free. You need this to get one of the best Pickpocket perks, so it's one you will likely want either way.
Perfect Touch
(level 100 Pickpocket Skill required)
Can pickpocket equipped items. That means everything, even clothes the victim is wearing. Just make sure your sneak skill is high enough, or approach them while being invisible and with the Muffle spell activated. You can't steal clothes if the target knows you're there!
Pickpocket Strategies
The Witch: Pickpocket by nature isn't an offensive skill, but if you want to try something new you can get the Poisoner perk and use it in combination a high level in Sneak and Alchemy. This will allow you to place poison in your enemies' pockets to weaken them or make them die instantly. If all three of these skills are high enough, you can even get away with placing poison in someone's pocket in the middle of a crowded town. Be aware that this strategy only works on people so Pickpocket won't help you in any way against the undead, animals, monsters, machines nor dragons.
Robin Hood: Stealing from the rich and giving to the poor, you might think? Well, not exactly. You steal someone's things and give it back to him after a little bit of tweaking of the item. If your skill is high enough and you have the necessary perks you can place self-made, self-upgraded and self-enchanted weapons in someone's pocket and they will use them the next time they're in combat.
The big benefit of this is that you can upgrade the armor and weapons of guards in Skyrim to make them more useful in the next dragon attack. If you are going to do this, you must leave one piece of clothing on the guards when you are upgrading the rest (for example, leave the boots). If you take all of their clothes they will spawn a new set and won't wear the upgraded gear. Guards don't work like followers who prefer higher armor rating above anything else. So you "give" their gear back, and might then pickpocket their boots to complete the set. Next time you visit the guard and check his gear, you will notice he is wearing the items you returned. Just don't expect a thank you.
One note here: guards outside the city will reset and not benefit from this tactic. Only the walled cities will work (those involving a game loading screen). So Whiterun, Riften, Solitude and Windhelm are all safe examples, and there are likely a few others you can do this in as well. After testing, guards from Whiterun were perfectly capable of slaying 10 Ancient dragons on Master Difficulty without the loss of a single human being. I didn't even have to give them Daedric weapons. I used Sky Forge Swords and Imperial Bows which I enchanted and upgraded with smithing to be extremely powerful. This was all they had been given.
This strategy is perfect to save the villagers of a town without your intervention during a dragon attack. It can also save you from Dragons if you flee to the guards. If you like this, you now have a new project to spend money on: 150 Grand Soul gems to upgrade all the weapons and armor of Whiterun guards alone.
Because they are Nords, I haven't upgraded anything with frost resistance. You can choose Absorb Health on your weapons if you want to, but I found that elemental damage is better as both enchantments add up to a +92 damage per element. On even a Sky Forge sword this is extremely deadly. The Fortify Destruction boosts are there to increase the power yield of the weapon enchantments. Yes, Destruction skill increases the power of flame, frost and shock enchants on weapons. Solitude Guards wear armor as well, so I would suggest giving them Fortify Archery and Fortify One-Handed enchantments. Or perhaps Fortify Block, if you already have given them Daedric weapons, which do extreme damage on their own. Below are the upgrades I've given the guards of Whiterun to prepare them for Dragon attacks.
Swords, Bows, and Daggers: Fire Damage, Frost Damage
Helm: Fortify Archery, Fortify Destruction
Armor: Fortify Healing Rate, Fortify Destruction
Boots: Resist Fire, Resist Shock
Shield: Fortify Block, Resist Magic (enchanted from Shield of Solitude, which gives a higher rating)
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