Ryan Chaplin

Ryan, OSCP, has performed penetration testing services for clients across a variety of industries from hospitals to non-profits to S&P 500 companies. He has been awarded for his work from numerous companies including NASA JPL. Prior to working in Offensive Security his work focused on the intersection of Software Development, Digital Marketing, and Security. He also enjoys playing basketball, reading, the arts, and watching way too much Netflix.

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The Exploit: Penetration Testing Insights From The Frontlines

The Exploit articles written by Ryan Chaplin

  • AI-Augmented Series: LLM-Aided Enumeration for Dormant WordPress Account Discovery

    AI-Augmented Series: LLM-Aided Enumeration for Dormant WordPress Account Discovery

     By Ryan Chaplin Ryan Chaplin leads off our Augmented-AI series with a scenario from a recent pentest using AI to write a script to discover an account to gain system access. November 12, 2025
  • Windows Kills Common Offline/Account-less Install Method
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    Windows Kills Common Offline/Account-less Install Method

     By Ryan Chaplin Microsoft Windows recently announced the removal of local-only installs on Windows 11. Raxis’ Ryan Chaplin looks at concerns and possible options. October 17, 2025
  • Dangers of Storing Sensitive Data in Web Storage: 5 Real Attack Scenarios
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    Dangers of Storing Sensitive Data in Web Storage: 5 Real Attack Scenarios

     By Ryan Chaplin Lead Penetration Tester Ryan Chaplin walks us through 5 real-world attack scenarios used in real-world penetration tests by Raxis. August 26, 2025
  • Password Series: 8 Practical First Steps to Crack Difficult Passwords
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    Password Series: 8 Practical First Steps to Crack Difficult Passwords in Penetration Tests

     By Ryan Chaplin From rulesets & hardware to wordlists and mask attacks, Lead Penetration Tester Ryan Chaplin shows how to crack difficult password hashes in penetration tests. February 25, 2025
  • Password Series: Defeating Emerging Password Security Trends with Psudohash
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    Password Series: Defeating Emerging Password Security Trends with Psudohash for Penetration Testing

     By Ryan Chaplin Lead Pentester Ryan Chaplin discusses emerging improvements in password security and how Psudohash can help bypass them on penetration tests. November 5, 2024
  • Meet the Team: Ryan Chaplin

    Ryan Chaplin, Lead Penetration Tester

     By Ryan Chaplin Ryan Chaplin, lead penetration tester, has loved tech since he was a kid growing up in Larry Bird’s hometown. Hear a few of his fun stories here! June 18, 2024