Pickpocketing the Skeleton Key is the most broken early-game exploit and nobody mentions it

[DragonbornVet]

I'm on my 4th playthrough and just realized you can pickpocket literally anything once you have the Skeleton Key from the Thieves Guild. Like, I'm not even talking about the obvious stuff - I mean you can walk into Dragonsreach and lift the Jarl's entire inventory piece by piece without triggering combat. The perk that boosts your pickpocket success rate on equipped items makes this absurd.

The real kicker is that if you rush the Thieves Guild questline (which takes like an hour if you know what you're doing), you can have access to every single item in the game before you hit level 15. I've been funding my entire playthrough by pickpocketing gems and potions off merchants, then selling them back to the same merchant. The game doesn't care.

I know the Skeleton Key is technically a reward for finishing the questline, but the fact that pickpocketing perks make it so broken that you can trivialize the entire economy by mid-game is kind of hilarious. Way more effective than the alchemy loop if you're willing to spend 30 seconds per NPC.

Has anyone else abused this or is it just me? I feel like this deserves way more attention than it gets. The pickpocketing tree is genuinely overpowered and everyone sleeps on it because they're too busy talking about restoration loops.

 

[WhiterunModder]

Honestly the Skeleton Key itself isn't the exploit - it's just a skeleton key, the real problem is that pickpocketing has basically zero consequences in vanilla Skyrim. The perk you're talking about (the one that lets you pickpocket equipped items) combined with the Key just removes the last bit of friction. You're right that it's slept on, but I think it's because most people don't realize how absurdly good it is until they actually try it.

That said, the merchant resale thing only works so well before you hit the fence gold cap or they run out of money. And if you're speedrunning the Thieves Guild just for the Key, you're kind of already committed to skipping most of the early game anyway. The real broken part isn't the pickpocketing - it's that Skyrim lets you do literally anything in any order with basically no level scaling. You can walk into a bandit camp at level 1 and if you're patient enough with stealth, you can loot everything and leave.

On modded playthroughs I usually just unequip the Key or use something like Requiem that actually makes the economy matter and gives NPCs awareness of theft. Vanilla economy is a joke regardless though, so if you're on console or just playing vanilla for fun, yeah, go ham with it. The game's not designed to be balanced against someone who's willing to spend 30 seconds per NPC.