SEC536: Adversarial AI - Penetration Testing AI Systems


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On the July episode of the SANS Stay Ahead of Ransomware livestream, we explored a significant shift in the threat landscape: ransomware operators are increasingly abandoning encryption in favor of data theft and extortion-only attacks. Joined by special guest Jamie Tolles from IDX, who brought to the discussion over 15 years of incident response experience and hundreds of ransomware cases, we examined the techniques threat actors are using to bypass traditional security controls and what defenders can do about it. Jamie went through several demos, so make sure and watch the livestream to see them!
The ransomware landscape is undergoing a fundamental transformation. According to a 2025 Sophos study, encryption events have dropped to approximately 50% of cases. Several factors are driving this shift:
We discussed how even organizations that paid ransoms frequently found the experience unsatisfying. Decryption was slow, data recovery incomplete, and the promised quick return to operations doesn’t happen.
Jamie demonstrated how threat actors use tools like Evilginx to bypass multi-factor authentication through session token theft. The attack flow is as follows:
The key takeaway? Standard MFA, while still recommended, is no longer sufficient. Organizations should implement phishing-resistant MFA using FIDO2-compliant hardware tokens that verify the authenticity of the domain before authentication.
The second demonstration showcased Bring Your Own Vulnerable Driver (BYOVD) attacks, where threat actors leverage legitimate but vulnerable signed drivers to gain kernel-level access and terminate security tools. The attack proceeds as follows:
Jamie demonstrated this against Lima Charlie, but the technique works against other EDRs as well. Once executed, the EDR console may show something such as "disconnected," leaving defenders blind.
Detection opportunities include:
Ryan shared his DEF CON workshop on EDR killers for those wanting a deeper technical dive into these techniques.
With encryption becoming less common, data theft has taken center stage. Jamie demonstrated Rclone, a legitimate cloud synchronization tool that threat actors have adopted for rapid data exfiltration. Rclone is fast, supports numerous cloud storage providers, and leaves several forensic artifacts:
Detection tips:
Ryan noted that while Rclone config passwords appear encrypted, they're actually only obfuscated and can be easily decrypted using available tools.
The discussion turned to backup strategies, with Ryan emphasizing the modern 3-2-1-1-0 rule:
Many organizations claim to have good backups but have never actually tested full-scale restoration. Testing a few files annually isn't sufficient. Organizations need to understand:
Jamie introduced CanaryTokens.org, a free deception tool that creates digital tripwires throughout your environment.
These tools require minimal setup with no account needed, and provide detection capabilities that threat actors can't easily anticipate or circumvent.
We'll be back on the first Tuesday of August at 1:00 PM Eastern. Mark your calendars and join us on YouTube or LinkedIn for more ransomware insights.
Mark your calendars for the upcoming SANS DFIR Summit in October, which now combines the Ransomware Summit, Threat Hunting Summit, and traditional DFIR content into one comprehensive event.
And remember to check out our upcoming SANS training events, including FOR528: Ransomware and Cyber Extortion, with a new course update, where we dive into the technical details of preventing, detecting, and responding to these types of attacks.


Mari DeGrazia loves the satisfaction of solving a good puzzle. That fascination paired with her technical abilities has made digital forensics the perfect career fit. She has 20 years of experience in the IT industry, including 10 years in DFIR.
Read more about Mari DeGrazia