I am currently trying to complete one of the radiant quest fishing jobs for the Thieves Guild. This particular job is to get an amulet from Melaran, a high elf in Solitude. Unfortunately my pickpocket skill is a rather pathetic 37 at the moment. However, I have an enchanted ring that gives a 28% bonus, a necklace that gives a 40% bonus and a potion that gives another 40%. Despite all that, I cannot pickpocket this guy without getting caught. I have tried over and over and he catches me every time. I have successfully pickpocketed other NPC's when my skill was lower and I had less bonuses available. Am I missing something here, or does this particular NPC just have some sort of off-the-charts awareness? Another question - when I have multiple enchanted items and potions, do those bonuses stack on top of each other or do I really just get the bonus from one of those? if anyone can give me some advice i would appreciate it.

Actually, wearing gear and using potions that increase your pickpocket success actually lowers it. It's a known bug, try removing your enchanted gear and trying it then.

edit: I'm not changing what I typed because I find it funny. Apparently today I'm employed by the department of redundancy department.

Really...hadn't heard of that one. I will try again without all the extras. Thanks for your help.

Just wait until they're sleeping. Your chances will be much better. If you have the perk anyway. That's what I did.

Where did you hear this? It makes a little sense to me after what's been happening in my game.

My pickpocket skill is at 100. I have an enchanted Necklace that fortifies 35%, a ring that fortifies 20%, and gaunlets that fortify another 35%. That's 90%!!

I also have the last two perks where you are supposed to be able to pickpocket equiped items and weapons.

Here is my issue: With all the fortifies, perks and skill at 100, why is it that when I try to say.....pickpocket Lydia's steel armor......I only get 5% chance to pickpocket that item?

In my eyes I should be able to take anything I want from anyone whenever I please. What good is getting all these perks and fortifies if it doesn't make any difference?

I couldn't even steal a set of tavern clothes off of a sleeping Orc with all this!!

You can always just save with you hiding behind the victim and reload every time it fails. The percent chance has to go in your favor eventually right.?

It's the same as the sneak bug, something about your skill being artificially raised over 100, aside from perks, causes it to reset. I have pickpocket 100 and Light Fingers 5/5 and I rarely get caught anymore. Just about everything says 90% including guard's armor and weapons.

You really don't need 5/5 lightfingers, I've got 100 skill 3/5 lightfingers and perks up to perfect touch and everything is 90%

Most stuff I do get the 90% success. It's the equipped stuff (which is why I got the last perk) that I can't get more than 5% success with.

Trying to steal 1000's of gold (from trainers) usually will be extremely low without perks.

I know, but I was messing around with it. I've wasted quite a few perks I realized I didn't need later.

Tried that. I stalked the guy at various intervals over the course of a day. All he ever seems to do is either sit in the lobby of the Blue Palace or stand around inside the ground floor of Erikur's house. Either way he never seems to sleep. At one point I was in there shortly after midnight and he was just standing around. I waited for 4 consecutive 1-hour periods and he just kept standing in the exact same spot like he was glued to the floor.

Yeah, I tried this approach. After about 15 fails I got tired on all the reloading, so I figured i would seek some forum help before I tried again.

I'm not a good pickpocket. I've tried. I've successfully pickpocketed 3 times out of four. I guess I didn't try very hard. I think two of those were during the initial "trying to get into the thieves guild" mission. I try it on bandits but it always goes south. Doesn't end well if you know what I mean, well not for them anyway.

Oh funny thing happened: Imagine this stupid Khajiit thief.... "Hand me all of your belongings or die!" encounter. Here you are walking around in dragonscale and reply "Do I look like I have any money?" And he buys it, or maybe he gets a closer look and realizes you gave him a way out alive.

You got me there