[Guide] How to Get 100 Pickpocketing

The short and sweet version:
- Get locked up in Solitude
- Pickpocket the key to your cell from the patrolling guard
- Make note of the guy across the cell from you
- Go get your stuff from the chest they place your confiscated items in
- Kill all the guards (Should only be 2-3)
- Now once the guards are dead go back to the guy in the cell that was across from yours before you escaped
- Pickpocket him to your hearts content and watch the skill raise...

Even if you are unsuccessful there is nothing that can be done, he will not report you and even if he did the guards are dead. What I did was take an item from his inventory, then placed it back in his inventory. Rinse and repeat for 100 pickpocketing.

Edit: This is unpatched and still works on 1.3

It's too hard to get my stuff from the chest and cannot kill the guards worth anything. Help?

lvlatt is EDGE said:

It's too hard to get my stuff from the chest and cannot kill the guards worth anything. Help?

Click to expand...

Only thing I can suggest is patience. Once you pick pocket the key to your cell from the roaming guard wait for him to go down stairs. Then open your cell... Sneak down the hall to the first door on your left right before the stairs. There will most likely be a guard in this room.

In this same room, where the guard is, there is another door to the left as you enter; your loot is in this room. You can either bolt straight to the chest and loot all, and equip your gear or try and sneak past him for your gear.
If you run he will be alerted to your presence so get your gear and equip it quick. After he is down it should be fairly easy as there should only be 2 more guards remaining. One will be roaming and the other will be static down stairs.

Good Luck

Calixto bug works great also. During the quest "Blood on the ice" You get the strange amulet. You can sell it to him for 500 through dialogue. Then pickpocket it, sell it right back to him. I saved after every successful theft and resale in case I got caught (which happened often).
I also got sneak up a few times and speech because you can persuade or bribe the guard if you get caught. You may have to initially decline selling it to him to get the "About that amulet" dialogue.