It's not a grey area. It's simply not enforced. If you're an investor and you find out that the co-founders gave you bad numbers to juice the next round (this is common to the extent that I have personally seen it multiple times), you have no incentive to get the law involved. You would lose your entire investment, instead of just some of it.

And oftentimes, the extra juice gives them enough runway to make things work. Cheaters win, that's the way it is.