Episode
28 September 2021 Official episode · Official transcript
cybercrime
An anonymized former Marine and cybersecurity consultant describes investigating fraud in Puerto Rico’s lottery system, using authorized physical and network penetration testing, database monitoring, and forensic evidence collection.
Topics: Warez software piracy and software cracking, IRC and early online communities, Digital forensics and incident response, Authorized penetration testing, Physical security and lock picking during security assessments, Windows 98 login bypass via an accessibility-feature exploit, Password hash extraction and cracking, Network enumeration and port scanning, Flat-network architecture and lack of segmentation, Reverse shells, Remote code execution against a Drupal server, Man-in-the-middle traffic monitoring, Database audit logging and real-time transaction monitoring, Insider threat detection, Physical and logical chain of custody, Lottery payout database manipulation, Money laundering through winning lottery tickets
Links published on the Darknet Diaries episode page. Not LLM output.
Qualified statements from this episode, not graph facts.
Os USES warez scene
Os says that in the early days he participated in the warez scene as an administrator, rooter, and cracker producing zero-day releases.
Explicit Confidence 99% · Os EP 101 Details
“I used to run around in the warez scene as a wares administrator and a rooter”
Os USES Internet Relay Chat
Os used IRC while participating in the warez scene and hosting distribution servers.
Explicit Confidence 96% · Jack Rhysider EP 101 Details
“So, he was on IRC, the Internet Relay Chat, and was setting up servers”
Os MEMBER_OF United States Marine Corps
Os joined the Marine Corps specifically to pursue computer and cybersecurity work and served five years active duty.
Explicit Confidence 99% · Os EP 101 Details
“I chose the Marine Corps specifically”
“I spent five years active duty”
Os USES digital forensics
Os performed defensive and forensic cybersecurity work in the Marine Corps and later at a consulting firm.
Explicit Confidence 95% · Os EP 101 Details
“So, I did both”
“They were doing forensics and other cyber-security kinda stuff”
Os USES penetration testing
Os conducted penetration tests as part of his offensive cybersecurity work and consulting work.
Explicit Confidence 98% · Jack Rhysider EP 101 Details
“he’s a pen tester”
“Os has done a number of penetration tests before he did offensive work while in the Marines”
Puerto Rico lottery OPERATED_BY Department of Treasury
The episode states that the Puerto Rico lottery is run by the Department of Treasury.
Explicit Confidence 99% · Jack Rhysider EP 101 Details
“It’s been running since 1934 and is ran by the Department of Treasury”
Puerto Rico lottery fraud INVOLVES Puerto Rico lottery
The incident concerned millions of dollars being stolen through the Puerto Rico lottery and manipulation of its payout system.
Explicit Confidence 99% · Os EP 101 Details
“we are losing millions and millions of dollars a month through the lottery of Puerto Rico”
“Someone inside the lottery IT team was going into the database and changing one number”
Puerto Rico lottery fraud INVOLVES Government of Puerto Rico
The investigation was commissioned and authorized by the Government of Puerto Rico, including the governor and government systems.
Explicit Confidence 98% · Jack Rhysider EP 101 Details
“The government of Puerto Rico hired this consulting agency to come do some work”
“The governor of Puerto Rico looks at me and the team”
Puerto Rico lottery fraud DISCOVERED_BY Os
Os and his team uncovered the database manipulation and traced it to an insider.
Explicit Confidence 99% · Jack Rhysider EP 101 Details
“Os has cracked the case”
“He’s figured out how the millions of dollars are being stolen from the lottery”
Os USES Metasploit
Os used Metasploit to find an accessibility-feature exploit for a Windows 98 system and later to identify an exploit against a Drupal web server.
Explicit Confidence 99% · Os EP 101 Details
“I’m like, alright; Metasploit, what do you have for 1998 Windows systems?”
“I go through the Metasploit table”
Os USES Windows 98 accessibility-feature login bypass
Os created and used a USB exploit to bypass the Windows 98 login screen and obtain local administrator access.
Explicit Confidence 99% · Os EP 101 Details
“ended up being able to create an exploit that I could plug in a USB and bypass the log-in screen”
“Drop it in, get full access”
Windows 98 accessibility-feature login bypass EXPLOITS Windows 98 accessibility feature vulnerability
The Windows 98 accessibility-feature login-bypass exploit exploits the accessibility-feature vulnerability described in the episode.
Derived Confidence 90% · Os EP 101 Details
“The accessibility feature – I can’t remember what the actual vulnerability was, but basically ended up being able to create an exploit”
Windows 98 accessibility feature vulnerability AFFECTS Windows 98
The accessibility-feature vulnerability is presented as affecting the Windows 98 system Os encountered.
Explicit Confidence 94% · Os EP 101 Details
“what do you have for 1998 Windows systems?”
“a log-in screen for Windows 98”
Windows 98 accessibility-feature login bypass AFFECTS Windows 98
The login-bypass exploit was used against a computer running Windows 98.
Explicit Confidence 99% · Jack Rhysider EP 101 Details
“puts it in the computer running Windows 98”
Os USES John the Ripper
Os extracted credential hashes and used John the Ripper to attempt password cracking.
Explicit Confidence 99% · Jack Rhysider EP 101 Details
“He then runs a tool called John the Ripper to try hundreds of thousands of passwords”
Os USES Password hash cracking
Os attempted to crack password hashes obtained from the compromised Windows computer.
Explicit Confidence 99% · Jack Rhysider EP 101 Details
“he grabs this hash file to try to crack the passwords on this computer”
Os included Nmap in his portable tool suite and used scans to examine the lottery network.
Explicit Confidence 98% · Os EP 101 Details
“a bunch of tools on it like Nmap and freaking man-in-the-middle tools”
“Nmap scans are also common”
Os USES network enumeration
Os enumerated the internal network to map reachable systems and identify the lottery network structure.
Explicit Confidence 99% · Os EP 101 Details
“So, I actually enumerate the network”
Os USES reverse shell
Os established a reverse shell on the long-forgotten computer so he could access it remotely from the hotel.
Explicit Confidence 99% · Jack Rhysider EP 101 Details
“he sets up a reverse shell to this computer”
Os USES man-in-the-middle attack
Os routed traffic through a compromised Linux server to capture and analyze traffic inside the lottery network.
Explicit Confidence 99% · Jack Rhysider EP 101 Details
“This is the man-in-the-middle attack that he was wanting to do”
Puerto Rico lottery fraud INVOLVES cartel
The lottery fraud was linked to a cartel operation involving money laundering through winning lottery tickets, according to the episode’s account of the investigation and court records.
Attributed Confidence 96% · Os EP 101 Details
“they were also running guns and drugs through that process”
“the court records show that they had someone inside the lottery who would produce winning lottery tickets”
cartel USES Puerto Rico lottery
According to the court-record account, cartel members used winning Puerto Rico lottery tickets to launder illicit cash and make it appear legitimate.
Attributed Confidence 95% · Jack Rhysider EP 101 Details
“they were using these winning lottery tickets to launder money”
“when they’d cash in the winning lottery ticket, they would get a check from the Puerto Rico lottery”
cartel USES BlackBerry phones
The indictment reportedly claimed that people in the cartel operation used BlackBerry phones to communicate.
Attributed Confidence 94% · Jack Rhysider EP 101 Details
“they used BlackBerry phones to communicate”
Puerto Rico lottery fraud INVOLVES Federal Bureau of Investigation
The FBI investigated the lottery fraud, received Os’s evidence, and took over most of the investigation.
Explicit Confidence 99% · Os EP 101 Details
“I immediately have to contact the bureau, the FBI field office in Puerto Rico”
“The bureau took over most of the investigation”
Puerto Rico lottery fraud INVOLVES United States Marine Corps
The incident account involves Os’s prior Marine Corps cybersecurity experience, which he drew on while investigating the lottery network.
Derived Confidence 78% · Jack Rhysider EP 101 Details
“Os has done a number of penetration tests before he did offensive work while in the Marines”
Jack Rhysider REFERENCES Full Metal Jacket
Jack references Full Metal Jacket and discusses a specific boot-camp scene from the film as an analogy for Marine Corps training.
Explicit Confidence 99% · Jack Rhysider EP 101 Details
“it reminds me of a very specific scene in the movie Full Metal Jacket”
Works mentioned in the transcript. Distinct from show-note sources.
Model gpt-5.6-luna · prompt 1.5.19 · schema 1.5.19 · 2026-09-13T07:17:01.684031+00:00