Caleb Stewart

Software Engineer, Penetration Tester, Reverse Engineer

Arlington, VA  |  calebstewart  |  caleb.stewart  |  calebjstewart  |  @calebjstewart  | 


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Software Engineering and Cyber Security Expert with Electrical Engineering background. More than 10 years software development experience in many languages from x86 and ARM Assembly to Python. Experience in SOC, Incident Response and Red Team roles. Passion for building elegant tools and frameworks to automate and simplify operations.


Huntress Labs
Arlington, VA
Security Researcher
Jul 2021 - Present
  • Technical expert performing static and dynamic binary analysis of malicious payloads.
  • Research and development of new features for Huntress platform to extend detection and response capabilities.
  • Testing partner software to identify, disclose and remediate potential vulnerabilities.
US Cyber Command
Fort Meade, MD
Task Force Technical Director
Jun 2020 - Jul 2021
  • Lead the research and development of capabilities and tools supporting DoD missions in cyberspace.
  • Developed and deployed software and hardware load-out for deployable incident response teams.
  • Developed incident response scenarios to provide analyst training and improve mission effectiveness.
  • Qualified Mission Commander and Host Analyst.
Coast Guard Cyber Protection Team
Washington, DC
Mission Element Lead
Feb 2019 - Jun 2020
  • First responder for numerous network security incidents threatening National Critical Infrastructure
  • Developed SOP and training requirements for incoming personnel.
  • Procured, configured and deployed state of the art incident response hardware platform.
Coast Guard Security Operations Center
Washington, DC
Infrastructure Support Branch Lead
Nov 2017 - Nov 2018
  • Operation and Maintenance of all network defence infrastructure including Intrusion Prevention and Detection Systems, Data‑Loss Prevention, Web Content Filter, and Firewalls.
  • Battle Watch Captain supervising security and operational control over all IT systems across the Coast Guard.
Coast Guard Cutter Bertholf
Alameda, CA
Combat Information Center Officer
May 2016 - Nov 2017
  • Responsible for combat and communications equiment and operational planning.
  • Assistant Command Security Officer ‑ managed physical, information and operational security programs for entire crew.
National Security Agency
Fort Meade, MD
Jun 2015 - Jul 2015
  • Applied systems‑programming expertise to reverse engineer unknown software and catalog all code‑paths for further analysis.
  • Performed static and dynamic analysis on malware to identify and report all observed activity.


Dec 2018
Offensive Security Certified Professional (OSCP) , Credential ID: OS-101-017541
Offensive Security
Oct 2020
Exploit Researcher and Advanced Penetration Tester (GXPN) , Credential ID: 9192230
Dec 2019
Offensive Security Certified Expert (OSCE) , Credential ID: OS-CTP-11344
Offensive Security
Feb 2020
Offensive Security Web Expert (OSWE) , Credential ID: OS-AWAE-02880
Offensive Security
Mar 2020
Certified Professional Penetration Tester (eCPPT) , Credential ID: 9831814
Feb 2020
Offensive Security Wireless Professional (OSWP) , Credential ID: OS-BWA-036075
Offensive Security
Dec 2018
Certified Information Systems Security Professional (CISSP) , Credential ID: 703304
Feb 2021
Offensive Security Experience Penetration Tester (OSEP) , Credential ID: OSEP-10202
Offensive Security
Mar 2021
Certified Exploit Developer (eCXD) , Credential ID: 9573003

Notable Projects

CVE Credits

Disclosed and assisted in remediation of the following CVE IDs: CVE-2021-42258, CVE-2021-42344, CVE-2021-42345, CVE-2021-42346, CVE-2021-42571, CVE-2021-42572, CVE-2021-42573, CVE-2021-42741, CVE-2021-42742.

Python, C, C#

Full featured agentless C2 platform built on top of a basic shell providing stable interactive sessions as well as an extensive pluggable API for automated enumeration, persistence, privilege escalation, and report generation.


Automated Capture the Flag (CTF) problem solver. Implements a multi‑threaded problem identification and solution framework capable of automatically solving cyber security challenges from a variety of categories.

Lead System Engineer, Challenge Developer
Python, Kubernetes, C, Assembly, GKE

Designed and implemented scalable automated event infrastructure utilizing Kubernetes on Google Cloud Platform supporting over 5000 simultaneous players with personally assigned challenge machines. Held events for multiple worldwide conferences and companies including HackerOne, BSidesBoston and GrimmCon.

x86 Assembly, C

Demonstrated expertise in low‑level software and hardware programming. Designed and implemented POSIX‑like kernel for the x86 family of processors. Full multitasking support. Custom device drivers for common hardware as well as implementations of common userland utilities.


U.S. Coast Guard Academy
New London, CT
B.S. In Electrical Engineering
Jun 2012 - May 2016