Adam Chester

Senior Security Consultant


Adam has over 7 years of professional experience in offensive and defensive security, specializing in conducting intelligence-led attack simulations for a range of sectors including large financial organizations and critical national infrastructure. With a focus on Red Teaming, Adam has completed numerous assessments aimed at identifying attack paths that adversaries could use to compromise critical assets and helping to secure customer environments against real-world threats.

Education & Certifications

Offensive Security Certified Professional (OSCP)

CHECK Team Leader (CTL)

CREST Certified Simulated Attack Specialist (CCSAS)

Industry Contributions

As a firm believer in free and open information sharing, Adam has spent his career developing tools and techniques to help further the skills of the offensive security industry. From working with a range of companies to identify and remediate vulnerabilities, to researching novel methods that Red Teams can use to avoid detection, Adam has contributed research openly with the aim of helping the Information Security community assess and defend against a range of adversaries.

Passion for Security

Adam has always been a hacker in the true sense of the word, never being content with the facade of a technology until fully exploring just why it works in the way that it does. This has led to many interesting findings over the years, along with countless caffeine-fueled nights spent in front of a disassembler.

Recent Blog Posts

Azure Application Proxy C2

With the ever-tightening defensive grip on techniques like domain fronting and detections becoming more effective at identifying common command and control (C2) traffic patterns, our ability to adapt to different egress methods is being tested. Of course, finding methods of pushing out C2 traffic can be a fun exercise during a Red Team engagement. A...

Tailoring Cobalt Strike on Target

We’ve all been there: you’ve completed your initial recon, sent in your emails to gather those leaked HTTP headers, spent an age configuring your malleable profile to be just right, set up your CDNs, and spun up your redirectors. Then it’s time, you send in your email aaaaaand…nothing. You can see from your DNS diagnostic...

MacOS Injection via Third-Party Frameworks

Since joining the TrustedSec AETR team, I have been spending a bit of time looking at tradecraft for MacOS environments, which, unfortunately for us attackers, are getting tougher to attack compared to their Windows peers. With privacy protection, sandboxing, and endless entitlement dependencies, operating via an implant on a MacOS-powered device can be a minefield....
View all posts from Adam

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