Justin Wynn MEMBER_OF Coalfire Systems
Justin Wynn says he is a senior security consultant and works for Coalfire Systems.
Explicit Confidence 99% · Justin Wynn EP 179 Details
“I’m a senior security consultant with Coalfire Systems.”
Episode
01 September 2026 Official episode · Official transcript
penetration test social engineering policy/law
The episode revisits the Iowa courthouse penetration-testing incident involving Justin Wynn and Gary DeMercurio, including their arrests, legal proceedings, industry response, later lawsuit, and eventual settlement.
Topics: Physical penetration testing, Physical security assessment, Red teaming, Social engineering, Door bypass techniques, Lock-picking, Alarm systems and alarm bypass, Physical access control systems, Remote network implants or “drones”, Security camera blind spots, Badge cloning, Rules of engagement for penetration tests, Legal and operational risks of security testing
Links published on the Darknet Diaries episode page. Not LLM output.
Qualified statements from this episode, not graph facts.
Justin Wynn MEMBER_OF Coalfire Systems
Justin Wynn says he is a senior security consultant and works for Coalfire Systems.
Explicit Confidence 99% · Justin Wynn EP 179 Details
“I’m a senior security consultant with Coalfire Systems.”
Gary DeMercurio MEMBER_OF Coalfire Systems
Gary DeMercurio says he works at Coalfire Systems and runs its Bellevue office.
Explicit Confidence 99% · Gary DeMercurio EP 179 Details
“I’ve been at Coalfire for six years”
Justin Wynn USES physical penetration testing
Justin describes his work as offensive penetration testing specializing in physical security and physical exploits.
Explicit Confidence 98% · Justin Wynn EP 179 Details
“I am an offensive penetration tester who specializes in physical security”
Gary DeMercurio USES physical penetration testing
Gary says he has approximately nine years of experience conducting physical penetration testing.
Explicit Confidence 98% · Gary DeMercurio EP 179 Details
“I’ve got about nine years of experience of physical pen testing.”
Iowa Judicial Branch USES Coalfire Systems
The Iowa Judicial Branch contacted Coalfire to conduct penetration testing on its courthouses.
Explicit Confidence 99% · Jack Rhysider EP 179 Details
“it was the Iowa Judicial Branch that called up Coalfire and asked the company to come and do a penetration test on the courthouses themselves.”
Iowa courthouse penetration-testing arrest INVOLVES Coalfire Systems
The Iowa courthouse incident involved Coalfire personnel conducting the contracted security assessment.
Explicit Confidence 96% · Jack Rhysider EP 179 Details
“the company that Justin and Gary work for”
Iowa courthouse penetration-testing arrest INVOLVES Iowa Judicial Branch
The incident involved the Iowa Judicial Branch, which commissioned the courthouse penetration test.
Explicit Confidence 98% · Jack Rhysider EP 179 Details
“The Iowa Judicial Branch has actually worked with Coalfire before to do other penetration tests.”
Iowa courthouse penetration-testing arrest INVOLVES physical penetration testing
The incident involved a physical penetration test of Iowa courthouse facilities.
Explicit Confidence 99% · Jack Rhysider EP 179 Details
“they’re specifically asking for a physical penetration test at five locations”
Iowa courthouse penetration-testing arrest COMPROMISES Dallas County Courthouse
Justin and Gary gained physical access to the Dallas County Courthouse during the assessment; the episode presents this as authorized testing, although the authorization was later disputed.
Explicit Confidence 99% · Gary DeMercurio EP 179 Details
“we walked up to the north door”
“we’re here testing the security”
Iowa courthouse penetration-testing arrest INVOLVES Dallas County Courthouse
The incident specifically involved the historic Dallas County Courthouse in Adel, Iowa.
Explicit Confidence 99% · Jack Rhysider EP 179 Details
“This one was actually the Dallas County Courthouse in Adel, Iowa.”
Iowa courthouse penetration-testing arrest INVOLVES lock picking
The courthouse assessment involved lock-picking, including picking doors leading to a courtroom.
Explicit Confidence 99% · Gary DeMercurio EP 179 Details
“I ended up picking two doors in a row to a courtroom”
Gary DeMercurio USES lock picking
Gary describes lock-picking as a capability he routinely uses during physical assessments.
Explicit Confidence 97% · Jack Rhysider EP 179 Details
“Gary is also really good at lock-picking.”
Justin Wynn USES under-the-door tool
Justin says Gary first handed him an under-the-door tool and taught him how to use it; Justin therefore describes using the tool as part of their work.
Explicit Confidence 96% · Justin Wynn EP 179 Details
“Gary was the first guy who handed me the under-the-door tool and taught me how to use this”
Iowa courthouse penetration-testing arrest INVOLVES under-the-door tool
The episode says the testers used or carried an under-the-door tool as one method for bypassing doors during physical assessments.
Explicit Confidence 95% · Jack Rhysider EP 179 Details
“these guys mentioned that they sometimes use an under-the-door tool”
Iowa courthouse penetration-testing arrest INVOLVES badge cloning
During the Dallas courthouse attempt, Gary tried a badge cloned from another building to test whether it provided multi-building access.
Explicit Confidence 99% · Gary DeMercurio EP 179 Details
“I tried a badge we had cloned from another building”
Iowa courthouse penetration-testing arrest INVOLVES security cameras
The testers located the courthouse security-camera monitoring position and observed camera coverage and blind spots.
Explicit Confidence 99% · Jack Rhysider EP 179 Details
“they took careful notes on what blind spots there were with the security cameras”
Iowa courthouse penetration-testing arrest INVOLVES Justin Wynn
Justin Wynn was arrested during the courthouse incident after law enforcement treated the physical test as trespassing or burglary.
Explicit Confidence 99% · Jack Rhysider EP 179 Details
“So, both of them get handcuffed.”
Iowa courthouse penetration-testing arrest INVOLVES Gary DeMercurio
Gary DeMercurio was arrested during the courthouse incident after law enforcement treated the physical test as trespassing or burglary.
Explicit Confidence 99% · Jack Rhysider EP 179 Details
“So, both of them get handcuffed.”
Iowa courthouse penetration-testing arrest ASSOCIATED_WITH qualified immunity
The later civil lawsuit arising from the incident was limited by qualified-immunity protections; the episode explains this as a barrier to suing government officials.
Explicit Confidence 96% · Jack Rhysider EP 179 Details
“qualified immunity means you can’t sue government workers, especially judges, prosecutors, and cops”
Kaiju Security DEVELOPED_BY Justin Wynn
Justin moved onto the team that he and Gabby established when Kaiju Security was created.
Explicit Confidence 98% · Jack Rhysider EP 179 Details
“Justin moved on to the team shortly after it was formed.”
Kaiju Security DEVELOPED_BY Gabby
Gabby says she and Justin built Kaiju Security after deciding to start a new company with different practices.
Explicit Confidence 99% · Gabby EP 179 Details
“We had a vision of — we wanted to do things a little bit differently, and so, we did that with Kaiju.”
John Strand ASSOCIATED_WITH Awareness Con
John Strand organized Awareness Con in Adel to explain physical penetration testing and the security profession to the local community.
Explicit Confidence 99% · John Strand EP 179 Details
“we immediately went to the town of Adel, Iowa, and we did Awareness Con.”
Iowa courthouse penetration-testing arrest RELATED_TO Awareness Con
Awareness Con was held in response to the courthouse arrests and the resulting public controversy.
Explicit Confidence 98% · Jack Rhysider EP 179 Details
“a few people from the cybersecurity community got together and said, what can we do to support these two? John Strand came up with a plan.”
Works mentioned in the transcript. Distinct from show-note sources.
Model gpt-5.6-luna · prompt 1.5.19 · schema 1.5.19 · 2026-09-13T09:07:30.242513+00:00