Pickpocketing seems to be one of those skills hard to level up because... well, you run out of options. So how do you level it up? Is the trainer in Windhelm enough? I know there are potions to increase your pickpocketing skill, and i reckon they can be pretty useful, but my question is: how do you increase your pickpocketing skill without having to load your game if you screw up?

I don't like cheats and i suppose there are many. I just wanted to know if there's a safe way of leveling it.

The two things I did was Go with really light items with low value. It takes more attempts to get a skill point but they are almost guaranteed. And start off by pickpocketing bandits and other targets you were planning on killing anyways. If you get spotted it just means you lost the drop on them.

If you get caught don't load the save, just go with the flow, make a run for it. The game is MUCH more enjoyable if you play it that way.

Quicksave is your friend.

It's only difficult at the beginning, when you get caught a lot. At first I used the Thieves Guild Boots and a ring of minor deft hands - they gave me a 30 points boost of Pickpocketing skill. I trained on bandits, there are no consequences if you fail. I also pickpocketed people in their sleep with the Night Thief perk. The safest way is to steal light things of little value, it will raise your skill slower, but you don't have to deal with guards all the time.

I read that if you pickpocket items from bandits they are considered stolen items...

Pickpocketing jewelry levels it up fairly fast.I'm another one that doesn't like to reload a save,your actions do have consequences.

I see. Light things like, gold for example?

Keep trying outside of a hold on random people and use the 'calm' spell. That's what I'm doing in my let's play

isnt the chance of sucsess based off of value not weight? wierd, but you should still try for worthless things untill you level up some

Well i guess that's the price you pay for being a thief. Jewelry it is...

I don't really remember, but I guess they should, since you actually stole them. There's nothing like pickpocketing the weapon off the bandit you're about to fight

It's based on both value and weight. That's why gold is the best - it's light, but its value will contribute to a decent raise of the skills. You might also try to pickpocket lockpicks and jewellery.

I don't know how you feel about exploits, but there's a couple of ideas you might try. For example, paying a Pickpocket trainer and then stealing your money back or reverse-pickpocketing with the Poisoned perk.

I didn't see any big problems really. Starting out with trying to pickpocket sleeping targets, seemed easier. Targets that don't make a fuzz - like bandits or people traveling on the roads. If you get caught, pay the fine and continue pickpocketing

Well how would vendors tell the difference between a weapon i stole from a bandit and one i looted from a dead bandit? That is so beyond me.

Thanks for your pickpocket idea, i'll give it a go and try stealing at night when people are asleep and will go looking after those items

That's the way the game is. I for one can't fathom how a chicken can be a witness to the crime. Skyrim's a weird place...

Booo - I hate reloading. Just play it out. But to each their own.

It could be i have so many stolen items on me I wouldn't know where I got them from. The thing is I have never got a bounty for stealing from a bandit and to me that makes it a free attempt. Money comes so easy not being able to sell something is not a big issue.

I steal steel arrows from guards in town. I need them, plus they are one of the easier things to steal. Lockpicks and gold are good things to steal at first too. Do that enough, quicksaving before each attempt, and before you know it, you will be moving on to bigger and better items.

Thanks for your input Zod77.