The pickpocketing skill in Skyrim is possibly the most underrated and overlooked skill in the game. Everyone who has used it noticed how quickly it levels. You can get to 100 in little time compared to most other skills. When you get to 100 you have fun taking equipped weapons and clothes for about 15 minutes. After that you are ready to just abandon pickpocketing for the duration of the character.
I will be discussing mostly strategies but will dabble in mechanics and numbers too.
Lockpicking
If you use lockpicking when your character is a pickpocket you are doing it wrong! What is the point of opening chests and doors? Its to get items to use or sell. Well with pickpocketing you will get some great items to use and sell. It makes lockpicking pretty obsolete, especially when you can pickpocket equipped weapons. Yes, open some locks if you really want to but there is no reason to when you can pickpocket people.
You should pickpocket every key you see. This allows you to get into houses and chests without picking the locks. You have no need to pick locks because you have the key to most locks. The other reason to lockpick is to get rich but a skilled pickpocket should have plenty of money lying around.
Leveling and Legendary Skills
Pickpocketing is a very fast skill to level. This makes it the perfect skill farm. A build can easily get over 60+ perks without spending a lot of time doing so. With more perks gained quickly you can spread yourself a little more thin than a normal character while still being strong and viable. The easiest way to level any skill is to by train and pickpocket the back the money.
It is even better with patch 1.9, allowing us to make a skill legendary. I did this to pickpocketing twice in each of my playthroughs. This entire strategy as a whole gave me a reason to continue being a pickpocket.
Before patch 1.9 I would get bored with pickpocketing once I got to 100. When the skill is fully leveled and you can pickpocket everyone easily it is very unsatisfying. Now I take the master perk and go after the people of the hold I was in. I collect as much high end merchandise as I can and sell most or all of it. Then I make pickpocketing legendary and go back to stealing low end items like arrows.
You can level pickpocketing at any time without the bribery perk by visiting Orc Strongholds. Go to Karthwasten and bribe the Silver Bloods to leave. It costs you very little and the owner of the mine will pay you much more than you gave. Make sure to walk by the Orc miner who will inform you she is spreading the word about you and the strongholds will accept you. Make your way to a stronghold and start picking. Orcs have no prisons. When you get caught you will have to pay a miniscule fine, that's all. After you pay the fine you can continue pickpocketing the same person over and over. DO NOT PICKPOCKET THE CHIEF! He will not fine you. If you get caught picking the Chief's pockets you have one punishment, death.
Speech!
The connection between pickpocketing and speech is undeniable. As you know, the speech skill has great perks for a pickpocket who wants to sell a lot of expensive items.Together these two skills allow you to level quickly, get a ton of perks and become a respectable combatant in less than 5 hours of play.
Speech is easily leveled thanks to the level 30 perk Bribery. This is easily achieved, see below. When you fail a pickpocket attempt you can bribe or persuade guards to let you go. This raises your speech skill very quickly. Once you get a bounty you can talk to every guard in that hold and get a speech check worth of experience in speech. Bretons and Nords start with a level 20 speech skill, making the goal of level 30 even faster.
Speech leveling
If you go to Whiterun you can persuade the guard to let you in. Then get a mammoth tusk from the town random goods vendor (I will not say that guy's name, he's annoying!) and give it to Ysolda. There is a speech skill book in that same guy's General Goods Store.
After Whiterun take a ride to Riften. A trip to Riften can boost you many levels quickly. Get the Dibella blessing from Haelga's Bunkhouse. You'll be able to pass the persuasion checks for the Riften gate, Maul, the Black Briar guy Unigrien, the guard who guards the Riften Jail, the Argonian woman Wujeeta, and help Shadr by persuading Sapphire. There is also a speech skill book sitting in The Ratway. You may not be able to persuade Maul right away so avoid him until you get a few more levels in speech.
Persuasion
By getting all of the speech bonuses in Riften and Whiterun you will be well over level 30 and get the Bribery perk. This perk lets you pickpocket without fear of getting caught because getting caught pickpocketing is a good thing! You bribe the guard to look the other way, leveling your speech. Just be careful, you can only bribe the same guard once every two or three days. Make sure you get caught near a different guard. I always pickpocket the arrows from a guard who has caught me as a way of marking which guards are safe and which ones will arrest me. If the guard has his arrows I know I didn't persuade him yet.
People often underrate pickpocketing for several reasons. A lot of people save before pickpocketing and reload if they get caught. That can be annoying and time consuming. Another flaw with the skill is how quickly it levels. I get to 100 and start being bored with it. If you legendary the skill you will find it fresh and interesting again.
Here is a link to the speech page on UESP. Use it as a guide to find the speech checks your skill level can succeed at. http://www.uesp.net/wiki/Skyrim:Speech
Pickpocketing Strategy
As I said, during my playthroughs I "legendaried" pickpocketing twice which means I leveled it to 100 3 times. Each time was different from the others. During the first run through pickpocketing your skills are low. You don't start with the Persuasion perk. I spent a lot of time digging for arrows and bribing Orcs to not kill me. Their bribe was only 20 or 25 gold and I was pickpocketing much more than that. The perks you gain from pickpocketing during the first run through are very important. You must take a couple for the pickpocketing skill and remember to hold enough perks for Persuasion when you get it. High on the priority list is to perk your primary offensive and defensive skills. Your character level will be increasing swiftly and if you only perk your non-combat skills you will die at least once every 5 minutes.
During the second run through the pickpocketing skill your choices will be different. The skill will level even faster now that you have Persuasion but you still need to be careful. By now I usually find some pickpocketing potions and enchantments. They are great when your skill level is very low but beware! If your skill level is higher and you use a potion or enchantment to boost it you will actually harm your chances. The chance to succeed when pickpocketing is capped. When you go over that cap with potions or enchantments you will actually have a lower chance of succeeding! Once you have the first perk or two in pickpocket you can drop the enchantments and potions. Your combat skills will be stronger than the first run through the pickpocketing skill but you do need to be careful with your perk placement. Make sure you aren't too weak or spread thin. You can spread your perks out more than a normal character but you still have to be a little smart with them.
The third run through the pickpocketing skill is the most fun for me. By now I am seeing everyone as a potential mark, someone to steal from. Your character level should be around level 40-50. This run through pickpocketing isn't about gaining perks. You can now finish off your skill leveling (training then steal back the gold) and become a real powerhouse. If you get caught you don't have to persuade or bribe the guards. You now have enough power to fight your way out of trouble if you choose to.
Removing Stolen Tags
You can clean stolen tags from items very easily. One way is to give them to your spouse/follower and buy them back. My favorite way is one I discovered accidentally. Find a container to put your stolen items in. The container has to be one you can take from, not steal from. If it has the "steal" icon over it you cannot use it. What you do is place the items in the container and have your follower take them out. When you take them back from your follower the stolen tag is now gone! After getting the stone from Bleak Falls Barrow go to Dragonsreach and give it to the court wizard. Next to his bed is a small dresser that should now be available for this trick.
Combat
Pickpocketing is also a combat skill, as you already know. Reverse pickpocketing poisons is a great way to silently kill. Killing/harming even a hostile NPC with poison is silent and their death will not alert anyone, as long as you are hidden from the other NPC's. If you place numerous poisons onto an NPC one at a time they will drink each of them consecutively until they die, any remaining can be looted. Placing a stack of 10 poisons in at once will only make the NPC drink the first and place the other 9 in his inventory. They must be done one at a time but can be placed without going out of his pocket and back in.
Slipping an NPC poisons is not considered a hostile action. If the NPC catches you then that is considered an assault, however if you are not caught then you can be wide open and detected by both the target as well as other NPC's and it will not be a crime. You can literally murder people right in front of guards (or guards themselves) and as long as they don't catch you for pickpocketing them it is perfectly legal. This is perhaps the single most useful application of the pickpocketing skill for anyone using Alchemy. If you create a posion that is tied to a buff and slip it to an NPC they will drink it but only the posion will affect them, they don't seem to gain any bonuses.
Perks
The only absolutely necessary perk is the first one. Not all 5, just one. After you take it everything becomes a lot easier to steal.
I like to think of it in terms of pickpocketing trainers. After you hit level 50 on a skill training costs a lot more. At that time you need more perks to take back the money easily. Night Thief and Cutpurse are the ones you want to go for.
Taking more than 1/5 in light fingers isn't ever necessary. It does help to take 2 or 3 of them if you have a lower skill level and are going for higher priced goods.
You can take other perks depending on your character and strategy. Keymaster is always pointless, don't take it because keys are at 90% anyway. Poisoned is worthless too unless your character plans to silently kill people via reverse pickpocketing poisons. Extra pockets can be very helpful but never necessary. It gives you 100 extra carry weight, good for any thief, and can be boosted more than that by taking a fortify restoration potion (I think that's it and not fortify pickpocket!) right before selecting the perk.
What I do usually was to go straight up the middle. I take only 1 in Light Fingers, 2 if I really need the help. I stop at Cutpurse. Right before I make the skill legendary I take the last 2 perks that allow you to steal equipped items. Then I steal some high end merchandise from high end people, legendary the skill and start all over.
If you do not want to legendary the skill, and I rarely legendary any skill, it is advisable to not take the last 2 perks (Misdirection and Perfect Touch) at all. They are fun at first but get very boring. You will have fun playing with them though, taking good items and leaving people naked. Its fun to do this to a group of enemies before you attack them, evening the odds because pickpockets aren't usually the toughest people. In the end you will get over the concept of taking equipped items very quickly. Take them since you never did before and enjoy the fun but expect the fun to die down soon.
Summary
- Pickpocketing can bring you both fortune and power. Use it to train any skill for free.
- Making the pickpocketing skill legendary will let you farm it for all of the perks you desire.
- Use the Persuasion perk in Speech to pickpocket without fear of getting caught and going to jail. Even if you get caught and go to jail you can just pickpocket the guards for keys that open the evidence chest and prisoner belongings chest.
- Orc strongholds are a training ground for the novice pickpocket.
- Remove stolen tags with a "safe" container and your follower.
- Poisoning people via reverse pickpocket is a silent kill and doesn't alert anyone to the danger. The only time the person will turn hostile is if they catch you in their pocket, just like regular pickpocketing.
- With pickpocketing and training you can get to level 20 in less than 5 hours of gameplay!
I hope you enjoy this post and it enlightens you to the beauty and enjoyment of pickpocketing, a skill that once was thought to be annoying and almost pointless.
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