some background..................im level 52 well over 130hrs in -sneak-100 but my pickpocket is about 30(if i want to take i kill!) but i have started to do the thieves guild and trying to get them return to glory(if it ever happens?..........when do these mini missions stop?)

how do you increase your pickpocket skill??surely there must be another way rather steal poor [censored] from poor people to increase skill??

iv had the master training from the guy in the cistern but cant do the mini missions now as always getting caught.


ANY IDEAS FELLOW TRAVELLERS AND THIEVES??

take a risk and attempt high value items.

or, reload until successful.

or, pay for training.

or, take appropriate perks.

Jewelry levels it fastest but there is a high risk.
Drink fortify pickpocket potions to minimize the risks involved.
The higher your pickpocket skill the better the chances of success,perks help a lot too but that might not be much of an option for you now.

As for the mini jobs that would be a spoiler.

I've found that putting that first +20% pickpocketing perk opens up a lot for you, as far as making it possible for you to steal decent items.

- Wear the Thieves Guild armor that gives you the % pickpocket skill (boots I think?)
- You can also make pickpocket potions
- The perks help a ton (not to mention the Extra Pockets perk gives you 100 extra carry weight which is very nice)
- The actual skill is increased through either training or actual pickpocketing, so practice, practice, practice. Make sure you're not detected. A lot of the success with pickpocketing is really about timing. When you click on "pickpocket target", you will see the "% to steal" in the window that pops up when you click on the item you're about to pickpocket. The higher the percentage, the smaller chance you will get caught. Anything above 60% or so is pretty safe. I tend to just save my game before a pickpocket attempt so that I don't have to go through all the hoopla with getting caught and going to jail or whatnot. It's faster to just reload at that point.

SPOILER!

Do most of your pickpocketing on Guards at night in Riften. Just pickpocket everything they have (except their weapons, since they will always have 0% chance until you get the final perk). If/When they catch you, just say you are in the thieves guild and the guard will clear your bounty at a discounted price, and you get to keep the items. The cost of the discounted bounties will add up, but it's a whole lot cheaper than using a trainer.

I've got only 29 in pickpocket and I get 90% chance to steal some of the lower value stuff. I think it's way to easy...
Anyway, the only way to increase this skill is pickpocketing. Just go and pickpoket as many people as you can...

Get the first perk and night thief, then simply go to windhelm at night and start going in people's houses (the high-class houses) and steal jewlery, which you'll have 90% chance of stealing unless it's enchanted. I got from 34 to 51 in one night (game night), by the way I play on master, however I don't know if this affects the odds of pickpocketing.

My experience is that taking the first two Lightfingers perks + TG armor = 90% most of the time. I can't imagine ever needing any more perks from that tree with the exception of Extra Pockets--which has absolutely nothing to do with the pickpocketing skill.

My alchemist likes having the one for poisoning.

It's funny. I tend to train my Pickpocket up every few character levels. I have a lot of gold and nothing to spend it on. However, I don't like to train skills I use all the time, so I get training in Pickpocket, it is like a hobby for my character. My skill is in the 60's now.

However, I have only picked one pocket in this game.

Pickpocket is the easiest skill to raise IMO. Every fool in Skyrim seems to have a lockpick and some gold that you can grab, even at lower levels. I take anything above 40% chance, and just quick-save every few items so that i can reload if i get caught. takes about 1/2 an hour to get to 100 if you move from city to city.

Just steal from everyone. It's a great skill to have. I role as a thief so it's normal for my character to steal from everyone. You may not want to do that for your character, but I must say, it doesn't take very long to get your pickpocket skill way up. In the beginning I used to steal everything each NPC was carrying, whether I wanted it or not. And I must admit I did my fair share of saving and reloading to ensure that if I were caught I could reload. But, now I am a wealthy and experienced thief. So, I get caught very little. And when I do I just pay off the guards, or persuade them.

My advice to anyone who wants to build the pickpocket skill is simply to do it a LOT. And invest a few perks into it. They are worth it.

If you want to be cheap and level it as fast as possible it is extremely easy. Just save before taking an item, if successful save again and take something else. If you fail reload. This is tedious at low levels especially on consoles.

Since I was the leader of the guild I just tried to pickpocket anyone, if I am caught I pay the minimal 12 gold bounty (I'm with the guild), then go back to stealing everything. I had the and I also had a few potions to increase the pickpocket chances.

Once I got to a certain level most items were 90%. I just spammed the take button until I took everything. If I got caught I paid 12 Gold and repeated.

Both these ways were cheap and boring, but it's very easy to get to 100. I got from 30-100 in around an hour if not less. I had tonnes of potions that made it easier to level at first though.

I only tested this pickpocket out at first. I reloaded back to my original pickpocket level as I found it weird to grind to level my skill. I prefer to do it over time.

If you want to know how to level up really fast in pick pocketing then wear something that will give you the best chance of pick pocketing like an enchanted ring with pickpocketing or enchant your own ring with pickpocketing if you can. Next make or use invisibility potions and drink the potion before you pickpocket someone. Then only pickpocket jewelery from the person like gems, rings, necklaces. The higher the value the better. If you steal things worth about 500 coins each them you will level up your pickpocketing skill by a level just by stealing a couple of these things. Travel to all the major cities to get jewelery off the majority of people. oh and I forgot to say everytime you make a successful steal from someone save your game before you steal from the next person because you will sometimes get caught and need to reload the game again.

I would suggest training, pickpocketing the trainer and get the money back, (Save), then repeat.

Another great idea and another reason why skyrim if such a good game. multiple ways to do things to get you what you want.

why save?

steal gold and if your caught u keep what u stole previously. you'll make money, and raise skill. with the small annoyance of being relocated to the outside of the local jail occasionally. then u start to get jewlery worth a few hundred with 50+% odds and it climbs fast. unless your anol about having no arrests, the fines are low enough to not matter.

they should really think about an increasing fine for repeat offences, at least within a time limit. trying to steal a 1000 gold necklace getting caught, walking to the jail, paying 25 gold, and going up to the same person to try again.

Several people have said that jewelry raises it the fastest, and this is sort of true but not quite. Taking GOLD levels it the fastest, especially once you get to taking around 100.
Best way to level pickpocket is to get a bunch of money together and run around placing money ON people (about 100) and then taking it AWAY from them. You can gain one skill point every time you repeat this.

Once you get up to 50, 70, 90 skill, you use more money. I went from 100 to 200 to 500 to 1000 to 1500. I made it to 100 skill in about 30 minutes.

It costs a lot of money because you have to pay fines when caught, and you risk losing your coin to the person you give it to. Works well in cities though, because if you get caught there are more NPCs to try next. Some of them have exceptionally low skills, and you can succeed 10 or 15 times before getting caught, even with low skills.