[mnutt]

The downside for him may be that users don't really care whether they got a cracked version or a legitimate version when their computer gets infested with malware; they're going to write angry posts about it online and say his software is broken or broke their computer. So it may be in his brand's best interest to keep users from using malware versions, even if those users may deserve what they get.

[Ecio78]

The downside for him is that now also the average user has enough tips in order to crack the official trial by him/herself without risking to download it from peer to peer or other unknown site :)

[raffi]

I look at this as knowing my audience. I sell software for penetration tests and red team assessments (e.g., to hack into stuff; not check a box). The people who use my software easily have the skill set to do what I wrote about and defeat any anti-piracy measure I come up with. What to do? I think it's best to be very customer friendly, trust my audience, and make light of the 1337 cr4x0r who thinks they won a game I won't bother to play.