Paryah

That one does work, unless I add an opener to it. Then it doesn't anymore.

...an opener?

Like Shadow Strike or Cheap Shot.

You def don't wanna add an offensive move to a Pickpocket macro tho -- once your target is in combat, you can't pickpocket them, and I'd figure that any "in progress" pickpocket would be cancelled.

Ah, ok. Then how in the heck does it work for others, like @MisterSmath posted earlier?

Oh, huh. Yeah, I'd already forgotten that they say theirs works -- I'm starting to question my brain. Within the macro I provided, where are you putting your Shadowstrike cast? Macros are far from my expert area, but I wonder if the /cleartarget at end would short-circuit a ShS.

I tried slapping it on the end, and yeah, it broke it. *shrug* I'm mostly just confused at this point.

Just for kicks, try removing that final /cleartarget. I use it in my macro because I usually *don't* want to attack, so by clearing the target it helps ensure I won't accidentally start stabbing them.