So I trained a level of destruction magic with Faralda for about 1900 gold.

I just picked cutpurse, so when she went to sleep I attempted a steal for gold.

My % to succeed was 9%.

So I equiped my necklace, +18% and ny ring of major deft hands, +25% and my % success became 0%....

Yet before I took cutpurse, my success rate to steal aboht 1200 gold with items equipped and when target was asleep was somewhere around 30%.

I don't have the patch, but I didn't see anything in regards to what appears to be +% pickpocket gear giving negative affect to pickpockwting attempts.

Also I gave Lydia, my follower a dwarf shield and now that, along with her steel shield are flagged as her starting gear. I was going to dismiss her to see if this fixed but I haven't yet.