Having recently gotten my sneak to 100 (Congratulate me--it's the first skill I've ever maxed out in an Elder Scrolls game), I picked up the Shadow Warrior perk. Now I'm trying to see if I can play like this, as overpowered and ridiculous as it clearly is: http://www.youtube.com/watch?v=KETNiqHg0oM

But I'm still having a hell of a time popping into stealth mode right in front of enemies and getting those assassinations (I do have the backstab perk, of course, and the DB handwraps that push the damage modifier to 30X). I can do it every so often, but not consistently. So I have some questions for any who have mastered this.

Is there a trick to it? What's the best way to time it--strike the second you go into sneak mode, or wait a moment? And should I be waiting for the "HIDDEN" message, because I don't seem to be getting it--the eye is always wide open, even when I occasionally do pull off an assassination.

And even though my sneak is 100, should I still be wearing sneak-improving gear? Would it help?

Thanks in advance.

You can press crouch and attack at the same time to make it easier or just strike as long as you're invisible for that second. The biggest problem I had is that at first I was always touching the enemy, so even invisible you won't be hidden if you're basically grinding on them.

Also in the video it looks pretty clear that the character have the Agent of Stealth activated too(before the first kill theres no combat at all as she crouches and becomes invisible... after the first kill(combat mod active) its all about the Shadow Warrior perk and relatively high bonuses to sneak, possibly from the first perk on the tree, the Stealth one, but not necessarily).

Helpful tip. Make some invis potions and tag them to your favorites menue. That way you can simply crouch, pop a potion, and assassinate when in a tight spot.

Thanks for the advice.

I'm actually glad it's tricky to pull off. When I do, it's very satisfying. I cut the throat of a Dremora Lord that way yesterday, and it was worth the 5 or so re-loads it took to accomplish.