We are witnessing a crisis of information security. Massive data monitoring is both a condition and an expression of this crisis. Connected whistleblowing cases like the Snowden leaks deal with both – they result from these conditions, act against them and have to consider them during the process of revelation. Whistleblowers therefore need expertise in cybersecurity, just as investigative journalists do. However, the interview makes the point that this is not just a technological issue. The ‘problematization’ of truth-telling in digital cultures is much more complex. It is connected to large-scale transformations of highly digitized societies under the conditions of surveillance capitalism. The following contribution presents an interview with the investigative journalist, cybersecurity specialist and privacy activist Micah Lee, and discusses the challenges of truth-telling in a powerful global surveillance apparatus and the crisis of information security.