Like most of the collective achievements in Skyrim, there’s no real shortcut to this achievement, you have to put the time in and pick locks and pick pockets. Simple as. In truth, most of these will just come with playing the game (especially the pick 50 locks) and the pick 50 pockets can be sped up when doing the Thieves Guild. A few tips though:
- Always open jail cells and chests you find around Skyrim, even if you don’t necessarily want anything from in there. -
Always carry enough lock-picks. Buy whenever possible. Even breaking them earns you experience for that skill, thus making it easier to lock pick.
- Doing the Thieves Guild’s final mission, “Darkness Returns,” you’ll be able to get a special ability that will help you remain incognito. No spoilers! Use the standing stone, the Shadow Stone and once a day players can become invisible for an extended period. That helps with pickpocketing. You’ll find it south of Riften, in the small mountain in the middle before the big mountain range to the south.
- You have to be crouched to pickpocket, and do so from the shadows and only grab when the reticule’s eye is closed (i.e. a thin horizontal line).
- Remember, it’s free to look, but grab something and get caught and they’ll turn on you and you’ll get a bounty. Always note the percentage… 90% ones are fairly risk free.