A Guide to Skyrim Speech and Pick-Pocket Boosting

This guide will give a brief overview of some methods any player can use, involving bribing guards as part of the Thieves Guild, within the video game The Elder Scrolls V: Skyrim. This method can be used by players in order to quickly raise their Speech and Pickpocket skill which is separate from the Ungrien, Black-Briar glitch which seems to have been patched in some instances of the game.

You can find a YouTube video of this method being performed here.

Setting Your Skyrim Character Up

Besides downgrading your game, you can instead begin your boosting methods by joining up with the Thieves Guild in Riften, which your acceptance into will provide many benefits beyond just what we will be using with this guide. The benefit worth note for raising Speech and Pickpocket is the ability to bribe town guards where you have a bounty, in order for them to ignore your crimes for the time being.

The next step once you’re an official Thieves Guild member is to build up a small bit of bounty in one of the various holds, or governing locations of the major cities across the land of Skyrim. You can do this easily by stealing an item off a shop keepers counter and running for the hills until you can fast travel to a safe location, since the shop keep will likely turn hostile and try to whoop you for pocketing their valuables. Wait at least 3 days and the shop keep should have forgiven your transgression enough to let you into his or her sight again without trying to shank you.

Boosting Your Speech and Pickpocket by Bribing Guards

Now you can turn around with your newfound bounty and begin boosting your speech and pickpocket skills by talking to the various guards that patrol any region located within the hold you have a bounty in. For example, if you have bounty in Whiterun hold, this will work with any guard in the city, the surrounding farms, patrolling the roads or occupying forts or watch towers and smaller residences like the town of Rorrikstead. Typically these guards will also have the name of their governing hold, but occasionaly while still under the same authority, will possess a name akin to their locality.
IE: The guards of Ivarstead are named “Ivarstead Guard” yet still respond to bounties of their governing city and its hold, being that of Riften and The Rift respectively.

These guards will often mutter “Wait… I know you.” which will clue you in to your wanted status, typically only saying it in passing unless your bounty is particularly high, in which case they will intercept you with a dialogue menu. Respond with “You’re making a mistake…” to which they will insist and demand you pay for your crime.

Next is to choose the option mentioning “I’m with the Guild. How about you look the other way?” to bribe the guard and give yourself a heft y boost to your speech skill. This will cost a significant amount more than you’re actual bounty, so make sure to keep you’re bounty low and have some extra gold on hand.

The next step is to immediately crouch into sneak mode and pickpocket your target for the gold you just paid, plus any extra they had in their pockets before, which is always placed into their inventory after the bribe. This action will shoot your pickpocket up far higher than the bribe will if succesfull and allow you to continually rinse and repeat this process with other guards.

Protip: Save your game after the bribe so you can reload if your pickpocket fails for less serious interruptions while you skill boost.

Final Notes for this Speech and Pickpocket Boosting Method

Each guard can only be bribed once every three days or so, so make sure to do the rounds and keep a mental note of which guards you bribed before, saving before you start the dialogue if you are unsure of their previously bribed status. Fast travelling to various locations is also a good way to make time pass in-game while looking for new guards to bribe.