I have a Thieve's Guild 'Fishing Job' to retrieve Wuunferth the Unliving's Flawless Diamond and return it to Delvin. Try as I might, I get caught every time.

I have a Pickpocket Skill of 40 with perks of:
Light Finger 1/5
Night Thief

I am wearing gauntlets of Pickpocket +36% and a Ring of Pickpocket of +36%

Even with these enhancements it shows a 0% chance of success even while he is sleeping.

Is my only option to go back to Delvin and admit that I can not do this job?

Takk

Or you can enchant items with Fortify Pickpocket.

You quit any of his or Vex's jobs with the only retribution being:
1) They complain and/or insult you.
2) You get a failed quest in your journal.

I found the Fishing Jobs to be more difficult than normal Pickpocketing. I enchanted 4 items with Fortify Pickpocket for the few jobs of those types that I did. And for some reason it seems to be more difficult to Pickpocket people who are sleeping than those who are awake. FWIW you can do any type(s) of Small Jobs for Delvin/Vex - you don't have to a specific number of each.

Oh, and I forgot to mention that I take a potion of Fortify Pickpocket +67%.

Both the Gauntlets and Ring are enchanted (my Enchantment is 100 with the Extra Effect perk - I wish I could double enchant an item and my Alchemy is 78 @ 4/5 and Benefactor perk), so I can craft some nice stuff.

What about this: I take a Potion of Paralysis and either throw it at him, poison my bare fists, or give him a light wound that does not kill him. I read that when the target is paralysed or unconscienous, you can take anything from them no matter the success rate.

I like the creativity, but I don't think it counts as a Pickpocket for the purpose of Delvin's Job.

I had to use 4 pieces Enchanted at Fortify Pickpocket +40% (no Perks in that constellation) and I believe my chances were at like 80%.

Edit:
I just verified that the gear was, in fact, +40% (4 pieces). My Pickpocket skill is 76 (probably what it was when I was doing Fishing jobs because I don't pickpocket except to be nosy and see what people have every now and then).

You could try leveling pickpocket a bit-- I'm playing a thief now and the first two (and so far only) skills I have at 100 are Sneak and Pickpocket. Pickpocket levels extremely fast, though it svcks in the beginning. But you're passed that stage now.

I have just spent a bit of time experimenting with my thoughts of using the paralysis potion, bare fists, a low level weapon etc to disable him. No luck. When I either get him on his knees or paralysised, I do not get the pickpocket option.

So right now unless there is other suggestions, I will either leave this for a future attempt as per medsteele or else follow buckom and admit to Delvin that I am not up to this task.

Does anyone know the algorithm for pickpocket between the 'hand' and 'mark'?