Hm. I imagine the former is some kind of way to bypass the restriction, which is why the achievement is named that.
But for the latter, I really tried. Made every single bad decision. I don't know if Caly counts, but now that I've finished the full game I might give it another shot.
If you select the red options (with the Walkthrough turned on) you will get it. The last path you can lose is Nova's so the achievement should trigger right after you refuse to save her from the Egyptian server at the beginning of 0.3 (while talking to Calypso).
