What's Your Problem?

Infiltrating an International Ransomware Gang

Apr 8, 2025

Jon DiMaggio, Chief Security Strategist at Analyst One, dives into the dark underbelly of the LockBit ransomware gang he infiltrated using wartime spy tactics. He shares gripping insights on their recruitment strategies and motivations, including shocking attacks like the one on Sick Kids hospital. DiMaggio discusses how international governments countered this menace, using innovative methods to take down their operations. His tale challenges perceptions of cybercriminals, highlighting an unexpected friendship with one, offering a complex view of human connection amidst chaos.

33:14

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Episode guests

Jon DiMaggio

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Quick takeaways

Jon DiMaggio's infiltration of the LockBit ransomware gang revealed their strategic operations resembling traditional business practices in cybercrime.

Law enforcement's innovative tactics, including psychological warfare and mock data leak sites, transformed responses to ransomware threats, highlighting adaptive strategies in digital security.

Deep dives

Microsoft Security's Role in Cyber Defense

Microsoft Security aids organizations in staying resilient against an increasing number of cyber threats, with over 600 million attacks being detected daily. By processing vast amounts of data from trillions of signals, it provides businesses with deep insights into potential vulnerabilities and upcoming threats. This proactive approach enables companies from various sectors, including automotive, sports, and banking, to innovate confidently while safeguarding sensitive information. Such capabilities underscore the dual responsibility of security, as it is equally a priority for the organizations and their technology partners.

Intro

2min

Infiltrating the Lockbit Gang

14min

The Dark Reality of Ransomware Attacks on Vulnerable Institutions

4min

Battling the Lockbit Threat

10min

Transformative Experiences in Cybersecurity and Business Innovation

3min

Navigating Life's Challenges and Fictional Hacking

2min

A Complex Friendship with a Hacker

2min

A few years ago, a ransomware gang called LockBit rose from obscurity to extort over $100 million from organizations around the world. A security strategist named Jon DiMaggio wanted to understand how the organization worked. So he used the techniques of World War II-era spycraft to make contact with the hackers.

On today’s show, Jon tells the story of LockBit – from the way it borrowed techniques from mainstream companies to market itself and attract talent, to the response from international governments that used the gang’s own tactics against it. And he talks about how he got the hackers to talk to him.

Jon described the rise and fall of the company in a series of posts he called the Ransomware Diaries. You can read those here: https://analyst1.com/ransomware-diaries-volume-1/

Note: This bonus episode of What’s Your Problem? is sponsored by Microsoft.

See omnystudio.com/listener for privacy information.

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What's Your Problem?

Infiltrating an International Ransomware Gang

Episode guests

Podcast summary created with Snipd AI

Quick takeaways

Deep dives

Microsoft Security's Role in Cyber Defense

Insights into Lockbit's Operations

The Impact of Hacking Strategies and Missteps

Law Enforcement's Innovative Countermeasures

Remember Everything You Learn from Podcasts