I picked up that quest where I am supposed to tell a Jarl about a vampire advisor.

Well the vampire is in Riften. I see the vamp and told the Jarl. She wants proof (I guess the glowing red eyes could mean anything). So I need to pick-pocket the vamp and get a letter. Well I can't. I only have a 29% chance (I'm a warrior, no sneak or pick-pocket perks) but that doesn't seem to matter as the guy always sees me anyway, even if I drink an invisibility potion. The vamp just moves from bench to bench to chair, etc. and can always spot me. So I never get the closed eye sneak icon, I can never pick-pocket the letter so I can never convince the Jarl.

Is there another way around this or some trick to get the letter?

Try a fortify pickpocket potion?

Or just kill the vamp when no one can see you and report to Isran.

I can't pick-pocket at all since I never get the closed eye sneak icon. I followed him around for a day and did get him in a side room once (no guard) but it was brightly light and he just kept sitting down on a bench against the wall so I could never get behind him.

I tried attacking him several times but he always sounds off an alarm and the rest of the castle joins in to kill me.

I think I'm just going to have to do the DG MQ and hope this goes away after that is complete.

I've done the DG questline a couple of times. This is one of the tougher quests depending on how your character is built. It was easy enough on my sneaky character (even with no pickpocket skill).

My warrior just thought he had to do what he had to do. He knew he was a vampire, so he struck him done in sight of the guards. He took the murder rap and the paid the fine (surrendered right after the vampire was dead). I liked that morally gray area for the DG - they're not knights in shining armor... except for the heavy armored ones. They seem more of a 'whatever it takes' faction.

If you're Thane of the Rift, you could use that to get out of it too.

In the end, you've got to do what feels right with your character. I don't think the side quest will go away though. You need to complete open quests before anybody else at the DG will give you new side quests. Good luck.

I thought about becoming Thane and trying it. The 'fine' for pick-pocketing is only 25 gold (I learned after my many failed attempts of getting it). If I can get the guards to ignore that I will still have the note to give to the Jarl. I'll have to give that a shot.

You don't need a closed eye to pickpocket. Just crouch right in front of him and open up his inventory. Take the letter. If you get caught, pay the fine, come right back and do it again until you are successfull. Then kill him after speaking to Jarl and watch everyone in the Longhouse go nuts as you whale on him.

Actually, the one I find tough to do is the secret pilgrim/bard. I got one in Ivarstead and that was easy: I just took him over to Shroud Heath Barrow and killed him. I also got one in Dragon Bridge and got a vampire attack, so I stood next to the "pilgrim" until the vampires killed him for me. In the other two cases I couldn't figure out how to get the pilgrim into a hidden spot, so I just assassinated in plain sight. Having done the Thieves Guild reputation quests meant a) I saved money and b ) could just walk away after paying my bribe without being transported to the local hooscow.

Save, pick pocket, load if fail. Repeat till success. Unless your odds of success are 0.

Alternatively you could frenzy the guy, thus making him a threat and things will take care of themselves from there. Or you could just bum rush him and run for it. Since there's no way to really 'provoke' people in skyrim there's not much else you can do.

I don't think that is true. My chance is 29%. I did the save, pick, reload trick about 20 times in a row and never got it. I'm convinced that pick-pocket is always 0% if they see you. Heck I even did it after drinking an invisibility potion and still get caught.

I have pickpocketed fine with the eye open. I am not sure save/reload changes the random number generator.

It's not 0% if they see you. At least with these advisors' orders i've always had to pick them while they saw me, took a few tries of reloading but in the end i always walked away with evidence and a raised brow of astonishment. Seemed kinda weird but oh well... (that was on the warrior/cleric character so low pickpocket too)

I found a ring that adds 20% so PP so I'll try it again.

Problem is right now I'm storming the castle with Serana to kill her father so I'm not sure the quest will still be there when I finish up the DG MQ.

If you wait until around midnight, the vampire assassin is usually outside the Jarl's bedroom door, he has his back to you as you approach him, which makes him and easy kill. Time it right, and the patrolling guards will not notice anything. Think of this quest as Splinter Cell with a sword, and you''ll be fine.

Do you know if they actually kill people if we don't take care of them right away ?

Good question, I never really thought about it. I had an open quest to help a Jarl for some time, and when I finally got around to completing it, all was ok. If I remember right, it was Solitude, and everyone was there upon my return. I have not read anything regarding the vampire assassin actually having a successful kill.

Its not a vampire "assassin." Its an "advisor."

If you absolutely want to have the eye closed to pickpocket him, what I did with my warrior character is when the vamp sits on the bench I jumped on the bench beside him. This makes for a weird situation where you crouch beside him, almost on his shoulder, but the eye should be closed. I had to reload quite a few times though cause I got caught all the time.

On my second playthrough I just killed the [censored] in front of everyone and paid the fine.