One of the most critical security protocol problems for humans is when you are betraying a trust, perhaps for some higher purpose, and the world can turn against you if you're caught. In this short paper, we report on efforts to enable whistleblowers to leak sensitive documents to journalists more safely. Following a survey of cases where whistleblowers were discovered due to operational or technological issues, we propose a game-theoretic model capturing the power dynamics involved in whistleblowing. We find that the whistleblower is often at the mercy of motivations and abilities of others. We identify specific areas where technology may be used to mitigate the whistleblower's risk. However we warn against technical solutionism: the main constraints are often institutional.