In this episode of Tech Talks Daily, I caught up with Raj Samani, Chief Scientist at Rapid7, to unpack the rapidly evolving world of ransomware. Raj has been on the front lines of cybercrime response for years and has seen firsthand how these attacks have professionalized. Gone are the days of casual ransomware notes asking for a few hundred dollars. Today, these groups operate like fully formed businesses with help desks, R&D teams, and carefully designed extortion models.
We talked about how ransomware has become a reputational risk issue more than just a technical one. Raj shared that CEOs are often more concerned about data being exfiltrated and leaked to the press than they are about systems being locked down. It’s no longer just about recovering files. It’s about trust, public perception, and the long tail of brand damage.
One of the most revealing parts of our discussion was how these attacks typically unfold. Raj walked me through real-world scenarios where criminals have remained inside networks for months, even years, before launching their final payload. He also described how careful planning, coordinated strike days, and threat intelligence can disrupt an attacker’s kill chain before irreversible damage is done.
We explored the uncomfortable truth that many organizations still fall victim to basic attacks because of poor cyber hygiene. While the threat landscape is becoming more sophisticated with the use of zero-day vulnerabilities and social engineering, many breaches still happen through exposed RDP ports or convincing phishing attempts.
Raj also offered candid insights into the ethics and complexities of ransomware negotiations, why outright banning payments may backfire, and what companies should do in the first few hours after discovering they’ve been hit. He made it clear that cybersecurity is no longer just an IT issue. It affects everything from supply chains to public services and daily life.
Is your organization prepared for the moment when ransomware moves from IT’s concern to the boardroom’s crisis?
