Darknet Diaries - 179: The Courthouse - Revisited

Episode Date: September 1, 2026

In this episode we follow up with Gabby and Justin from Episode 59 - two seasoned penetration testers who tell us a story about the time when they tried to break into a courthouse but it went... all wrong, and what happened in the aftermath.SponsorsThis show is brought to you by Doppel. Doppel stops AI attacks with digital risk protection, human risk management, and email security on a unified social engineering defense platform.doppel.comThis show is brought to you by Sinch. Sinch is the cloud communications platform businesses build on to send SMS, make calls, and verify identity at scale — including the one-time codes and two-factor prompts that stand between an account and whoever's trying to get into it. Learn more at https://s.sinch.com/4xc8dnzSupport for this show comes from ThreatLocker. ThreatLocker is a Zero Trust Platform that gives organizations control over what can run and what users and devices can access. It combines prevention with real time detection and automated response, helping security teams stop unauthorized activity and quickly contain compromised machines. Learn how ThreatLocker can strengthen your defenses at threatlocker.com/Darknet.View all active sponsors.SourcesFull list of sources on the show page: https://darknetdiaries.com/episode/179/

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Starting point is 00:00:01 This episode is supported by Raxus. Think about what it takes to hire someone to break into your own building. You're trusting them inside your data center, your server rooms, past every control you have. Many companies can't take on that responsibility, and many more won't. Raxis was created to solve just that. Since 2011, Raxis Red teams have physically breached some of the most secure facilities on the world. Banks, law firms, hospitals, energy infrastructure, and defense contractors, badge cloning, lockpicking, talking their way past the front.
Starting point is 00:00:31 desk, the skills to actually get in, and the discipline to do it with strict rules of engagement of you. Most firms have one or the other. Raxus has both, and every test ends with a recap that explains exactly how they got in and what to do about it. Raxus still does the hard parts just right. If physical security is critical to your cyber defense, then check them out at raxus.com. That's spelled RAXIS.Raxus.com. I just came back from DefCon, and it was so wonderful, meeting so many. of the listeners there. Many of you asked how my dad is doing. I'll tell you, he's struggling with the modern world. Let me show you what I mean. So like, I call my dad a few times a week just to check
Starting point is 00:01:15 in on him, but he only calls me when he's got computer problems. Let me play for you what one of these calls sounds like. Okay. So anytime I get a photo, or if I want to save it, there's like three little dots top right corner. Yeah. saving a photo. And I hit the dots because I want to save a photo. It used to say save. Now it says save to a count. So I'm clicking on that, save to account.
Starting point is 00:01:53 But the count is something called One Drive. I don't. Oh, it says add account. How do I add an account? Because one drive I don't use. I don't know what that is. This is ridiculous. You know, where did you get this tablet?
Starting point is 00:02:11 You gave it to me. It's like all of a sudden my photo, save image, is gone. Where did you get the photo? Well, I just pulled up any one so I could explain to you. Okay, so you took the photo. I took it on the tablet. Did I hear that right? He took a photo on his iPad of some.
Starting point is 00:02:35 some rabbits and doesn't know how to save the photo he took? It's always the most mind-boggling question that he throws at me. I saw the photo. It was dark and blurry. It was not even worth saving. But he manages to stump me every time with these tech questions. I'm just like, uh... Oh, wait a minute.
Starting point is 00:02:55 No. I found it. I found it. Pushing buttons. Good. You did it again. I'm going to go to photos and see if it's there. Yep.
Starting point is 00:03:07 I'm not really sure what the sequence is. In a nutshell, you figured it out for me. Good work. And there you go. He figures it out all at his own. Without any help from me at all, I'm just listening to the problem. And that's how a lot of these calls go. He just figures it out over time and then thanks me.
Starting point is 00:03:24 Now, as much as I hate handling these calls because it's just so mind-boggling and frustrating to me, I told him he can always call me if he ever needs tech support because he paid for my college to get a computer engineering degree. So he legit deserves free unlimited tech support for life because of that. And there was another call a few days ago where he got a new doctor and the doctor wanted him to fill out like a 25-page form of all his medical history and stuff.
Starting point is 00:03:51 While he was filling it out, he couldn't figure out how to send the form to his doctor. So he called me up. So do I hit the X and go to inbox? and then just forward that yeah you can send it to them in an email attachment okay then I'm gonna hit the X on this patient form
Starting point is 00:04:15 what patient form are you looking at the one that they sent me the one you filled out yep and it has all yeah now I went to my email does the patient form have all this stuff you typed into it
Starting point is 00:04:31 the one I I think it, yeah. Okay, so it's got your data on there, and when you hit X, did it ask you to save it? Stop, stop, stop. I just went to where I sent it to myself and there's nothing on it. Holy crick. No, none of this work. Yeah, that's not.
Starting point is 00:04:50 I'm asking you if it saved it. So can you open the form again and see if your stuff is still there? No, it's all gone. How is it all gone? Oh, you got to push save probably. all the stuff, you know? Yeah, that's one option. This call was particularly maddening,
Starting point is 00:05:08 and he was so frustrated that he lost all this data from filling out a 25-page form. It doesn't stay anywhere on here to save. I'm looking at the new form they sent me off freaking 25 pages, and nowhere does it say save and send. Okay, you know, one option is just go down to their office and say, give me the form, I'll fill it out right here. I got to go get ink and I got to print that. I got to fill this out of you. I can't do an hour
Starting point is 00:05:35 doctor's office. You got nothing else to do today. Prescription. When did you have surgery? Oh my goodness. Unbelievable. Oh my gosh. I know. I should have called you before. As you can see, he's not very good at file management. And I thought I could fix it for him. So I started remotely trying to connect to his computer, his home PC, to troubleshoot this. But after like 10 minutes of trying to connect to his home computer, I finally asked him. Spotify, one item. No, you're not, is this all on your iPad or is just on your home computer?
Starting point is 00:06:12 No, this is on the iPad. Oh, I didn't know that. I thought I was connecting to your computer. That's why I was using the software. If I would have known this from the get-go, I would have been trying a whole different set of the instructions. Oh, yeah, yeah. Oh, man. Okay.
Starting point is 00:06:27 Big computer doesn't work. So now his big computer doesn't work? Now there's three problems that we're trying to fix here, right? A lost form, a printer that's out of ink or something like that. I don't even know what the problem is there. And now his main computer doesn't work. Anyway, for some reason, I couldn't even connect to his iPad remotely on this one, and I just couldn't help him find this form.
Starting point is 00:06:48 I thought he might have saved it somewhere, or there might be an old revision of it somewhere that we could rescue, but this was one that I could not fix, and he didn't figure it out on his own. So he hung up and drove to the doctor's office to fill out the form there. But what is the deal with this? Why does he struggle so much to adapt
Starting point is 00:07:07 to the modern world like this? He's been using a computer every day of his life since the 90s, but his brain just can't keep up with the ever-changing aspect of it. Is it up to me to keep him afloat? Or has ignorance just no excuse anymore? These are true stories from the dark side of the Internet.
Starting point is 00:07:29 I'm Jack Recyder. This is Darknet Diaries. This episode is sponsored by Threat Locker. The weird part about modern cyber attacks is how normal they look. The attacker logs in from Chrome, uses PowerShell, runs a remote admin tool your IT team already trusts. There is no custom malware, no dramatic movie hacker moment, just normal tools used in the wrong way. That's part of why Threat Locker exists. Threat Locker helps organizations control what sort of.
Starting point is 00:08:17 software can run, what it can do, and how systems communicate. If attackers get credentials or land on a machine, they'll have a much harder time moving through the environment. Because security teams are realizing something important. Problem isn't always unknown software anymore. Sometimes it's trusted software, being used by the wrong person. If you want to see how Threatlocker works, go to Threatlocker.com slash Darknet and book a demo today. That's Threatlocker.com slash darknet to book a demo. This episode is sponsored by Dopple. Protecting yourself from attackers used to be as simple as deleting dodgy-looking emails, but with AI, the attack surface has outgrown the defense that legacy vendors provide.
Starting point is 00:09:02 Dopple was founded in 2022 to give companies back control. Dopple is an AI-native social engineering defense platform. Dopple strengthens human risk management by training employees to recognize deception and provides digital risk protections across every channel. It even delivers a gentic email security that doesn't just score the inbox, but takes down the attack infrastructure behind the message. Those dodgy-looking emails have been replaced by bespoke and personalized texts,
Starting point is 00:09:28 URLs, ads, and even social media connections. But Dopple can then turn these attacks your business receives to inform campaigns and security awareness training for your employees so they know what to look out for. Dopple, outpacing what's next in social engineering. Learn more at doppel.com that's spelled D-O-P-P-E-L. Dopple.com. Okay, this is the epic story of those penetration testers who broke into the Iowa County Courthouse.
Starting point is 00:09:59 I first ran this episode back in February 2020. It's episode 59, but I'm revisiting it today for two reasons. First, it's just a really good story. And if you haven't heard it, you definitely should be listening to it. And if you already heard it, you should listen to it again because it's that good. But second, a lot has happened since I posted that episode originally. And I caught up with the two people involved at DefCon last month to give us a full update on what has happened since, and it's crazy. So first, I'm going to replay the original episode right now, and then in the last 20 minutes or so of this episode, we are going to get an update to this story, and it's really interesting, so stick around to the end. All right,
Starting point is 00:10:38 let's go. All right, so let's jump in and meet our guests for this episode. My name is Justin Wynn. I'm a senior security consultant with Coalfire Systems. I am an offensive penetration tester who specializes in physical security, which often entails social engineering, physicalized exploits to gain access to facilities. Yeah, my name is Gary DeMecchio, and pretty much mirror everything Justin said, except I'm a managing senior
Starting point is 00:11:02 and I run the Bellevue office in Washington. I know they said it quickly, but the important part here is that they're both penetration testers. I've been in a coal fire for six years, and I probably did the military another three. I've got about nine years of experience on physical pit testing. Right. and I've been with Coal Fire for over four years,
Starting point is 00:11:20 so physical penetration testing for over four years. They've come here today to share some penetration testing stories with us. Now, even though these two live on opposite corners of the U.S., one Florida, one Washington State, they team up together on assignments all over the U.S. And the assignment is typically like this. A company will call up Coal Fire, the company that Justin and Gary work for,
Starting point is 00:11:42 and ask for a security assessment. And they might want someone to test their website to see if it's secure, or do a password assessment to see how strong the user's passwords in the network are, or conduct some compliance checks. And this is all to make the company more secure. The Iowa Judicial Branch is the State Department of Iowa. It's a government facility. And specifically, they handle the court cases and such within the state of Iowa.
Starting point is 00:12:08 So it was the Iowa Judicial Branch that called up coal fire and asked the company to come and do a penetration test on the courthouses, themselves. It was full scope, red team penetration test. So it included things like external pen testing, web application testing,
Starting point is 00:12:26 internal testing, which was to be done after we had gone on site to see if we could gain access into their internal network and kind of like do like a real life scenario. Like can you gain access to start facilities?
Starting point is 00:12:36 Can you plug in a, what we call a drone, a remote device to be able to access that network later once we're off site and then conduct the internal network penetration test from there. And throughout the whole time,
Starting point is 00:12:47 We're contacting with the guys at Iowa courts.gov. Justin and Gary get assigned to conduct the physical penetration test on the courthouses together. They've been working together for four years on doing physical penetration tests just like this. So they're used to each other and do good work together. And actually, I have a copy of the Rules of Engagement here in front of me. So let's see. Okay, yeah. So this is for the Iowa Judicial Branch.
Starting point is 00:13:11 And they're specifically asking for a physical penetration test at five locations. There's a judicial branch, the Polk County Courthouse, the Dallas County Courthouse, a juvenile justice center, and the criminal court area. Five locations, and the window to test the security on these buildings is between Sunday, September 8th, and Friday, September 13th. So they had a week to do this assessment, and this was last year in 2019. The rules of engagement list out a ton of things. Do they have permission to tailgate behind someone to get in? Yes. Do they have permission to dig in the dumpsters?
Starting point is 00:13:44 Yes. Does coal fire have permission to use? lockpicks to get in. Yes. Does Clofire have permission to plug USB drives into computers that they get access to? Yes. Does Coalfire have permission to disable alarms? No. And the goal here looks like they're trying to get into the building, plant rogue devices, look around to see if there's any security problems like unlocked computers, passwords written down, that kind of thing. So, okay, the rules of engagement seem pretty clear.
Starting point is 00:14:10 So that gets filled up before we're on the call, and then as we're going through that with the client, the project manager is taking notes in there. So you may see things like, okay, at the JD building, we discussed with the client. Floors three and four are specifically off limits during daytime hours because there was going to be the Supreme Court convening, and they obviously didn't want us interrupting that. So part of that, we're discussing with the client on the phone. Yeah, during the daytime, do not touch, do not go on floors three and four. And then we enumerated with them. We're like, okay, well, like, what if we're in there after hours? Like, what do you want to see from there? Is that open access? And like, yeah, that'd be more acceptable.
Starting point is 00:14:45 but you know what, let's play it safe and just show us to see if you can reach the, the doors that enter on that fort. So the contract will say something like, okay, JB building, floors three and four are off limits. And like you see how big those fields are in that table. So it's really like the bare information that the project manager wants to be in there. And we have a good understanding with the client of what they're actually looking for. So actually, this Rules of Engagement document I'm looking at is 28 pages long.
Starting point is 00:15:13 and this field he's talking about is super small. All these things you cover on the call in great detail only get jotted down with a couple of words. It's not fully documented in the scope of work or rules of engagement. And these conversations are so granular. If we were to take and actually take the conversation that we had on the phone and write it out and put it in a contract, the contract would be 100 pages long.
Starting point is 00:15:39 The amount of discussion that we have on what it is exactly, want us to do, it would be unfeasible as far as a rules of engagement would be concerned. Right. And so again, that's why we have phone call. That's exactly why we have. So we can say, this is what we understand,
Starting point is 00:15:58 what exactly what you guys want, and then we're all on the same page when we show up. Like, we're going to be there at night and the client was like, yes, we want you to focus on after hours testing. So a lot of that stuff, unfortunately, which we never would have predicted or seen coming at us. We didn't capture in that which would have been great if we did.
Starting point is 00:16:16 The Iowa Judicial Branch has actually worked with Coal Fire before to do other penetration tests. So everyone seems to agree on what should be conducted and what's expected here. And an agreement was made. And they create what's called a get out of jail free card. This is a slip of paper that lists all the people who hired Coalfire to do this penetration test. This is their information security officer, their chief information officer, and the infrastructure manager.
Starting point is 00:16:42 These are three people who worked in Iowa's judicial branch who contracted coal fire to do these tests. And this get out of jail free card has their names and phone numbers listed with their signatures. So if these guys get caught, they can ultimately show this to get out of any real trouble. We touched down Sunday night. We entered in a facility, so I don't want to provide too many details that hadn't been already disclosed. All right, fine. Unfortunately, we're not going to be able to go into every detail of what happened. I don't want to expose any actual vulnerabilities over there at the Iowa County courthouses,
Starting point is 00:17:17 but let me give you an idea of what they're capable of. First of all, these guys mention that they sometimes use an under-the-door tool. So let me tell you what this tool does. It almost looks like a bent fishing rod. It's long, four-feet, metal rod, and it has a string on the end. And this is for doors that have a handle, that when you push down, it opens a door. So you try to slide this tool under the door. and then you pull it up using that string to get it close to the handle.
Starting point is 00:17:47 You try to hook it onto the handle from on the other side of the door, and when you do get it hooked on there, you pull down with both the string and the rod, and it pulls the handle down and it opens the door. It's actually pretty simple. And on top of this, Gary is also really good at lock picking, so he'll certainly have these in his pockets and ready to use them whenever he needs to. But with lockpicking, it might take you a while, maybe 10 minutes,
Starting point is 00:18:12 maybe 30 minutes to get a lock open. So it just takes more skill and time. If you're talking about my favorite, because I find this a lot in commercial buildings, is going to be crash bar doors, right? Either the ones that come down like the old high school gym type doors or the ones that you just push and go into the door itself. A von duPrint.
Starting point is 00:18:33 Thank you. They'll have the latch on the inside of the door. So you can't really use an under the door tool. They make some tools if you have door. double doors that come together without the, what's it called in the middle there? The mullion. The mullion, is that what it is? Yeah, there's another term four, too, but there's an inner, there's a bar that runs in between the doors where you're not supposed to be able to insert tools.
Starting point is 00:18:55 So you'll see a lot of those doors that don't have that bar that separates the doors. Those are really easy to get into. You just, you stick a tool inside, you turn it to the left or the right, and then you pull it open to the door. What we've come up with that, that what do you like to use, that's absolutely my favorite tool that is literally in my backpack right now is a cutting board. It's a really, really thin plastic cutting board that I bought from Amazon and I cut a notch in this in this cutting board. And so for crash bar doors, especially the single ones where you can't see anything, you stick it through the door on the edge of the door and then once you feed it through the
Starting point is 00:19:32 door, you pull it down until that cutting board rests on top of the latch. And then you'll apply pressure down on that latch and you start pulling the cutting board toward you. outward from the door until that notch that you cut falls on top of the latch. So now what you've got is you've got the back half of that cutting board on the other side of the latch, on the inside of the door, and you pull. And if that latch doesn't have the dead latch, latching it properly, you will open the door every time. So typically when we're talking about door bypasses, we're inserting a tool through whatever method that we can,
Starting point is 00:20:08 whether it's an interleaving double door system so you can go in between the doors or if there's a gap underneath the door, insert a tool there and start manipulating some mechanisms on the other side of the door, whether that's the Vonduprim Crash Bar or the latching mechanism itself or some peripherals like a request to exit sensor. But I can, what, 80% if you have to put a number on it,
Starting point is 00:20:31 80% of doors can be bypassed by bypassing the latch. Right. Just by manipulating the latch itself, you can get into 80% of facilities. And just coincidentally, can you tell us where you guys are this, or what you guys are doing this week? This week we're doing three two-day courses comprised of physical access control systems, alarm bypass techniques, and then safe manipulation.
Starting point is 00:20:53 So really kind of an action-pack week for us. That's all the kind of juicy James Bond style stuff. So you can imagine what kind of bag of tools these guys have to break into buildings to carry out assessments like this, right? I mean, they've got so many things I'm surprised that TSA even allowed them on the plane. So even though they can't get into specifics about what tricks they use to bypass the doors of these buildings, you can take a pretty good guess
Starting point is 00:21:15 that they've got many options they can use to get into each door that they've run into. So it's pretty much we walked up, assessed the perimeter and like kind of matched up with what we were seeing on Google Maps, things like that, and gain entry to that first facility on Sunday night to Monday morning. When we get into a place, it depends on,
Starting point is 00:21:33 it also depends on who is attacking, right? So if Justin is attacking, for instance, and he gets into the door and he's able to get in really, really quick. There's a certain, like, you know, like, he's your teammate. So you're proud, you're like, wow, dude, that was really fast. That was really, really fast. Justin and I have been working together since he's been here.
Starting point is 00:21:53 So you get to see this progression of somebody when he's on his first red team or second red team, I think it was, you know, with the guy. And then when he's on his, you know, 15th red team and you're like, dude, you're getting really, really, really good. But you get to see that progression. So it's a lot more personal, if you will, when you're on a red team with somebody that you've been working with for years of years and years. I'm going to say I'm tearing up over here because Gary, honestly, like, I do need to take a moment to think.
Starting point is 00:22:19 I'm, like, taught me so much of what I know. Like, yeah, of course, like, deviant and, like, some huge stars in the industry that you can learn so much by watching YouTube and, like, I learned how to assess security of your facilities. But Gary was, like, the first guy who handed me the under-the-door tool and taught me how to use this one. I didn't even know which end of the stick to be holding onto, which is a very common thing. When people are given in the under-the-door tool. So they get in, they look around for ways to plug in a drone and to take any photos of security problems
Starting point is 00:22:45 that they want to put in their report. They even found the desk of the person who hired them for this engagement. So they leave a little present on his desk to prove that they got in overnight and got access to his desk. But we had gained access and we left a calling card. I just left the business card on where the point of contact's desk to the point where the next day he had emailed me and said,
Starting point is 00:23:05 I guess I do congratulations. I mean, we're going back and forth every email. I'm like, yeah, I mean, we found some really severe vulnerabilities that, you know, minor fixes that you guys can use to dramatically improve the security of this facility. So going back and forth through things like that. So already in contact with the client, going through things like that. And then, yeah, Tuesday rolls around. So it's Tuesday night.
Starting point is 00:23:29 After the courthouse has closed for the day, they get up to the building and see it has two sets of locked doors to get into. We make it to the first door really easy. And then the second door, we could have used. used the same attack, but we were trying other things. Right. And we weren't having a lot of luck with the other things, but we didn't really want to try the first attack because we wanted to see if we could use different techniques to get in, right?
Starting point is 00:23:52 We found other areas that we could attack. So we went around a different area, and we were working on, Justin was working on one door and I was working on a nut. I don't know. Did you ever get that door open? Pick the lock, like all sort of dead. Yeah, like each way and like, no, there's something else was going on. There's a secondary latching.
Starting point is 00:24:07 That we couldn't see or something. I ended up picking two doors in a row to a courtroom, and then we ended up making it in, and then we ended up getting in. We saw the security, the security cameras. Now, when they say they found the security cameras, what they mean is they found the room that you can sit in to watch all the security cameras
Starting point is 00:24:31 and what's going on in the whole building. Guard desk, it wasn't really a room. It just they had security cameras at the guard desk, which was right, which was actually the security cameras, sheriff's desk during the day that sits there. So they've got a sheriff that or a deputy sheriff. Right. That monitor that's there on duty for the courthouse that sits in this.
Starting point is 00:24:52 It's almost like a front desk. Yeah, like press desk type thing. Where a receptionist would sit in a company. So the deputy sheriff sits there and has access to all these different cameras which show the courtrooms or office areas. And so at night when you've got your security guard there who isn't a deputy sheriff, they will also use those same cameras that the deputy sheriff and will say to check the different offices to make sure that nobody's in there, the lights aren't on.
Starting point is 00:25:18 So one of the first things I do is look at all the cameras to see if anyone was there, and they did in fact see someone in the building. Somebody was making their rounds, checking on the place, it looked like a security guard. They made sure to keep a close eye on him while sneaking around this building, and at the same time, they took careful notes on what blind spots there were with the security cameras. so when the guard got back, they could stay in those blind spots. As the guard went to a far end of the building, they started exploring around,
Starting point is 00:25:47 looking for security problems and being careful to stay very quiet. And as the two of them wandered around this courthouse, they opened a door which tripped an alarm. Suddenly, the doors were buzzing and the alarms were sounding. What had happened is they basically have a holding room next to the courtroom and both doors lock in that room. So whether or not that is for criminals that are in there to see if they can get released from jail
Starting point is 00:26:15 or if it's for somebody that's accused of a crime, whatever, not sure what it's for, but both doors are locked. So because I didn't want to have to pick the door on the way out in case it locked behind me, I propped it open. And because of the, again, an assumption, because of the people that are carried there, they make sure that if that door is left open,
Starting point is 00:26:34 that alarm sounds. So when I made it through both doors and I went to the next room, which had the guard post in it. That's when I heard the alarm, and then we ended up figuring out, oh, it's because we brought one of the doors open. Let's close that, duck. They were able to complete their security assessment and get out of there. The guard never found them, and maybe didn't even hear that alarm at all.
Starting point is 00:26:53 But another successful mission for these two. But that was fun. No, it's a great time. We were pooping and snooping and we were dodging the security guards, and he was looking at the cameras, and we were hiding out of stuff, and that was good stuff. They got through the courthouse pretty quick, and the night was still young, so they decided to hit up a second courthouse that night. This one was actually the Dallas County Courthouse in Adele, Iowa.
Starting point is 00:27:16 Let me describe the scene to you. The town of Adele is small. It has like 5,000 people living there at most. It's cute, though. It has like a historic Main Street, USA type of feel to it. In their downtown area, the roads are covered in like a red cobblestone brick, which gives it a more rustic feel. And all the buildings downtown look like. like they could all be historic buildings.
Starting point is 00:27:38 And the most prominent building in all of Adele is the Dallas County Courthouse, their target. And it was built in 1902, which absolutely makes it historic, three stories with those pointy spires on the top of each corner, and there's a large clock tower on top with a beautiful rotunda, towering way up high over the whole town. This is their target to get into that historic courthouse, in this sleepy little town in the middle of nowhere. So the two head on over to the courthouse.
Starting point is 00:28:09 Well, we stopped and got the bomb burrito at the gas station. Yeah, the head does come up there. We did have a snack. Physically. We did have her snack. We took like a 30-minute break and just hung out at the gas station and talked it to the... He was free donuts. Yeah, we did it.
Starting point is 00:28:26 So we had them out. He just gave us some free donuts. Yeah, so we had our break, which was literally, I mean, gas station was across the street. Just like almost across the street from the courthouse. So we sat there for 30 minutes. We kind of, you know, stokes the place out just to make sure that they didn't have some sort of patrol or something in those city cops or deputy sheriffs that were trolling the courthouse. So we parked at the courthouse. Oh, yeah.
Starting point is 00:28:52 And we, again, we've got to get out as Yale free card. And every other time, like, we don't have to be ultra sneaky typically in situations like this where they just want to see if Joe Public can get in the building, right? We don't have to be super simple. So this is one of those instances that if you look at the contract that we have, it specifically stated we were not allowed to bypass the alarm on this building. They did not want us to bypass the alarm. In the conversation we had on the phone, hey guys, don't circumvent the alarm, don't bypass it, just don't get radar security.
Starting point is 00:29:26 Like, don't disable a sensor that anybody could go up, bypass the storing and entry without alarm going off. So that's a pretty common theme with a lot of our clients. Like, we're not trying to degrade the security of their facility so we can gain access because it also allows potential for other threat actors to gain access, covertly or without setting out alarms. Right. So in this instance, we walked up to the north door, I think it was. So we go up to this courthouse. We jiggle the door.
Starting point is 00:29:55 Like, there's a little technique that you just see to, like, if Lash doesn't engage and pop the door real quick. And much to my surprise, the door was open. At this point, it's like midnight. Why in the heck is the front door open on this historic courthouse with all the lights off inside? Freaky, for sure. But Justin thought someone must have tried to close it at night, and it just didn't shut all the way. Now, this courthouse has an alarm system because it's a historic courthouse building, so yeah, it should, right? When he opened the door, the alarm did not go off.
Starting point is 00:30:33 So our assumption was there was a fault setting in this alarm system. The front door, they armed it anyway. Again, this is our professional guess of what happened. They armed it anyway, even with that fault, or they armed it, it counts down, they go out, and they didn't close the door all the way, and then it armed anyway without that front door being fully closed. So when Justin grabbed that front door, he opened it, what, two or three inches? And the alarm didn't go off. And then I tried the badge.
Starting point is 00:31:07 It cloned from another building just to see if they had multi-building access. That didn't work. And it's kind of like, well, should we give in the benefit of the doubt? Or should we just use this? And so we elected to basically close the front door and say, okay, let's start over. So they both stepped back outside. This time they closed the door all the way. It latches shut.
Starting point is 00:31:30 This must have been a flu. for the door to be accidentally left open or something. So they wanted to break in properly. Now, the door is locked and sealed properly. Okay, so they begin again. These two being masters at getting into these doors, they have no trouble getting the door back open. Now, as they get this door open,
Starting point is 00:31:50 they immediately hear the alarm is beeping. Right, just like in your home security system where you walk through the door and it starts beeping to let you know that you've got X amount of seconds to put in your code before the actual alarm goes off. So it was beeping really loud. Yeah, and we already had an idea before that. We kind of expected that alarm to go off.
Starting point is 00:32:09 So just, again, a little bit of precursor to that. The other locations, nobody had showed up, nobody respondents. We've been gaining access to government facilities without any alarms going off, without central dispatch showing up, without police presence showing up. So at this location, we're kind of coming up here,
Starting point is 00:32:26 and we've been there throughout the day and we had seen like the alarm panel said, okay, disabled. That night it said, okay, arms we would expect it to go off. We're coming up to this facility, hoping for once this final facility, the alarm would go off
Starting point is 00:32:39 at this location. So it was always like, you know, bittersweet, but like good, okay, great. The alarm's going like it's beeping at least once we go in there. At least it's armed. Right? So eventually the alarm counts down and then it starts sounding.
Starting point is 00:32:56 So very audible at this point. The entire downtown of Adele is going off and you can hear the sounders going off. The sleepy town of Adele is now being woken by these alarms coming from their precious, historic, iconic courthouse building in the middle of town. So at that point, alarms are blaring throughout downtown. We decided to go up to the third floor. So we're very well aware at that point.
Starting point is 00:33:22 It's very audible that the alarms have been activated. They've been tripped. And at this point, we go up to the third floor, get a vantage point in hoping that police presence responds to the incident. to the alarm going off. Because it's not uncommon. I've been in banks in the past, literally 100 feet from a police station where they were not paying for the service
Starting point is 00:33:41 or wasn't connected or configured properly where it didn't dial out and call police to respond to the incident. So it's not terribly uncommon for that to happen. So we go out to the third floor, get a vantage point, and at this point for reporting purposes, hoping that police respond to the alarms going off.
Starting point is 00:34:01 At which point, you know, within, it was extremely response time. Within five minutes, I think it was a sheriff's deputy had showed up to the scene. And we see him and he's going around the building. Gary and I are conferring with each other. Okay, man, what's the next plan? What are we doing here? Like, there are police? Like, it's a very, not a high-stress situation,
Starting point is 00:34:20 but you have to handle it professionally and properly. Otherwise, there always is risk in those types of situations. So we're discussing our game plan, what we want to do. Within a short while, another couple minutes. We go out on the main floor, Gary's calling out commands. Like, is there an officer in the building being very verbal, trying to get in communication with police? At that point, it didn't sound like anybody else was in the building.
Starting point is 00:34:43 We didn't hear any doors opening or closing. So we start proceeding downstairs. As they go downstairs, they don't see anyone in the building. They don't hear anyone in the building. But they can tell there's a police officer right outside the door they came in on. They spot each other and Justin and Gary come to the door. officer, he's on the other side of the door. He was actually, we found out afterwards, was not able to gain access inside the building. So we're communicating with him. He's like, so, so what's up, fellas? And we're like, hey, man, like, we're here testing security.
Starting point is 00:35:14 Do you want to talk? Like, can I open this door? Like, just keep my hands static, not moving anything. He's like, yep, go ahead. Open the door. I'm like, okay, I'm going to open up the door now. And so we push the crash far. We walk outside and we greet him. At that point, just start conversing with them. officer we're here. We were hired by Iowa State courts. We're assessing security of various government facilities, including this courthouse. We have documentation. This is all above ground. Would you like to see our paperwork? He responds, yes. Say, okay, it's in my back pocket. Do you mind if I make a move and pull that out of my pocket? Sure, go ahead. And then at that point, present our paperwork. So from there, he asked for our IDs. And at that point, I think somebody else had shown up right at that
Starting point is 00:35:54 point. So they were escorting us. They had hunkered down with us while somebody else how taking the IDs and the paperwork away and started verifying our information. Yeah, and at some point, I think the sergeant even told us to relax because we were trying to be ultra-careful and professional and every time we wanted to move our hands, we're like, hey, is it all right?
Starting point is 00:36:11 We're okay to get our wallets. And at some point he's like, hey, man, you guys can relax. We just want to verify that you're doing what you should be doing. You know, you guys can, you don't have to be that paranoid. We, we're pretty sure that, you know, you're not doing anything nefarious here. And they were ultra-professional. Like they, yeah, those guys were great.
Starting point is 00:36:29 Perfect. They were nice. They were professional. Like, they were doing the whole, you know, Ronald Reagan, trust, but verify type thing. Like, yeah, we're pretty sure you guys are on the up and up because you came out to us and you did what you were supposed to do. But we're just going to make sure we're going to verify that you are really supposed to be.
Starting point is 00:36:45 Right. And so we can't, you know, if nothing else, we can't thank the deputies enough because they were ultra professional and just really, really stand up. Agreed. Yeah. they immediately give the police to get out of jail free card. You don't want to mess around
Starting point is 00:37:01 and lie to the police. You want to come clean because this is not someone you want to try to trick. This is not part of the scope. You want to tell them, look, we're here on official business. The paper has the names and phone numbers
Starting point is 00:37:13 of the state employees that hired coal fire to do this penetration test. The police call the first number. No answer. They call the second number. That line was disconnected. They called the third number.
Starting point is 00:37:29 Someone picks up. The police asked if they knew that these guys were trying to break in the courthouse. And they said, yeah, we're doing security testing. Those guys supposed to be there. They're testing the security of the courthouse. And this is, you know, my story of what happened is. I'm not on that call there with them. They'd walk away a little bit from us.
Starting point is 00:37:44 This is what the sergeant, the deputy sheriff, who was a sergeant, told us he spoke to our contact. He's like, well, this is what your contact said. So they run our credentials and, you know, everything comes back. from our names and our driver's license. They do get a hold of our point in contact. And they'd say, yes, these guys are here testing security. So at that point, the sergeant, the die in charge for, or head head in charge. The ranking officer.
Starting point is 00:38:09 Thank you. That's what we're trying to get to. Had come back to us, hand us back our IDs. And he's like, as far as I'm concerned, you guys should be good to go. Like everything's all clear here. And so at that point, like things get really jovial. We're laughing, joking around with the officers. They're asking us, man, this job's crazy.
Starting point is 00:38:25 Like you guys break in a building. Like, how does this go? Like, how do you get jobs like this? Like, how can we, like, test security? Like, you know, how can we get a job like that? Just as Gary and Justin, we're about to leave another squad car pulls up. This one has sheriff written on the side. And the guy gets out and walks up.
Starting point is 00:38:46 The sheriff shows up. He's visibly upset. From our perspective, the mood completely changed. So prior to I'm showing up, everybody was happy and smiling. And there had to be eight deputies that responded. All of us standing on the courthouse steps. And then there was one city of an Adele officer there as well. So there was at least nine people there, including us.
Starting point is 00:39:11 It's not a lot going on. Adele, Iowa. When the sheriff shows up, all the smoking and joking stops, right? Like just giant fun sponge walks in the room. And everybody just stops talking. just everything just goes silent. And he walks up, he has some choice words to say to us
Starting point is 00:39:31 that we didn't necessarily agree with kind of talking down to us in a certain respect, to put it mildly. And basically tells us that we don't have authorization to do what we're doing. And asks us if we do that. And we told them our perspective,
Starting point is 00:39:47 which was they were under contract, we're working for these people. His response to that was, well, they don't own this court house. and I don't care if you write a contract. They don't own this courthouse. Whoa, what? The state doesn't own the courthouse?
Starting point is 00:40:02 Uh, did they get authorization from someone who didn't have authorization to break in the building? Uh, I would start to get worried at this point. But Gary wasn't worried at all. Not, you know, no. Because this has never happened before in history, as far as we know, or any of the other people that we know in the industry, it's never happened. people get taken away or they get held until situations resolve themselves,
Starting point is 00:40:29 not frequently, but it happens. So if that happened in this case, we were fine with that, you know? Right. Because we know the truth's going to come out. They're going to realize that we're actually working for a company and that we were really contracted by the state.
Starting point is 00:40:41 So, you know, worst case scenario, we've got to spend an hour or two in a holding cell, not that big of deal. The sheriff tells everybody that was there, says, well, we're going to arrest these guys for trespassing hold them, I'm going to go make a phone call. And so in our minds, he's going to go talk to our contacts, at least in my mind, that's what he was doing.
Starting point is 00:41:07 And in that time that he was gone, because he was gone for like a good 10 minutes, it felt like that. Yeah, that seemed like anyways, sure. And that time he was gone, the mood went right back to what it was before he was there, which was everybody was asking his questions, asking us how we did stuff, what's the craziest thing we've ever seen or heard about in our line of work.
Starting point is 00:41:23 Like, it went right back to that. One of the officers was super interested in how we got in, so we showed them our tools, we showed them how we got in, we showed them the tech that we troubleshot how we think that front door got left open. They gave us their ideas. We talked about card entry on why they originally couldn't get into the building. And it was everything was just went back to normal.
Starting point is 00:41:45 About 10 minutes later, again, we're thinking. He came back in and he was just like, you need to arrest these guys for burglary. And all the sheriff's deputy is kind of just, looked at each other. And the sheriff turned around and said, do I need to do it myself or something to that effect. I don't remember his exact words, but he said something like, do I need to do it myself, I told you guys to arrest them for burglary. And I don't know what Justin's, what, like, who the sheriff or the deputy sheriff was arrested of Justin. But he puts his hand in my shoulder,
Starting point is 00:42:17 says, hey, man, I'm really sorry about this. You're going to. I think something very. Yeah, see, he goes, turn around. I'm going to have to put these cuffs on hand. Right. Totally understandly, okay, man, like, I get it. Like, see where you're And both our responses are like, hey, man, it's okay. You're just doing your job. It's not a deal. This won't be the last time this happens. And so both of them get handcuffed.
Starting point is 00:42:37 They had their rights read to them, and the police started escorting them away. But still, even though they now have handcuffs on and the police are escorting them, they still weren't nervous about the situation. No. I mean, because thinking about it from our perspective, like, we had done nothing wrong. We have all the paperwork in the world. I'm from Florida. Gary's from Seattle. It's not like we flew out to Adele, Iowa to start breaking the courthouses on our own behalf.
Starting point is 00:43:02 We knew we had every shred of evidence in our favor. We knew that this is totally above ground. It's not totally uncommon for law enforcement to respond to incidents. It does happen. It is extremely rare, I'd say, for somebody to get detained or furthermore arrested. And that's as far as it had ever gone. And as far as we're aware, nobody's ever been actually formally a arrested and pressed with truth.
Starting point is 00:43:27 So there's ever actually charged. Right. So, I mean, we're thinking, okay, we're going to go to the station. We'll perk this out. Not a big deal. Now, because this is Adele, a small town, the jailhouse was literally across the street from the courthouse. So they both get walked to the jailhouse with handcuffs on. Stay tuned, because when we come back from the break, we'll hear what happens to Gary and Justin. This episode is brought to you by Cinch, 2F8, verification codes, fraud alerts.
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Starting point is 00:44:50 Gary and Justin are now both at the jailhouse and they have been separated and the police are questioning them and processing them separately. That's when the aggravation started to kick in a little bit because we were going through the entire process, which is empty out all your pockets, give us all your gear, give us your backpacks. I don't know if you ever did, but I interacted with the sheriff a couple of times.
Starting point is 00:45:17 No, I never talked to the sheriff. Yeah, so I interacted with the sheriff a couple of times, and it was like, hey, sheriff, are you just going to hold us? Are you actually going to charge us? And it was later discussed or during that conversation that I won't really go into because it'll just aggravate me was, yes, we're going to charge you. There was multiple times I tried to, I don't want to say talk my way out. So you have to escalate, right? Yeah, but yeah, that's a better term.
Starting point is 00:45:43 You escalate the situation like, hey, maybe you could contact one of our, you know, one of our contacts. Talk to somebody at Iowa State Court, you know, talk to somebody because we're legitimately just working here, sir. And we were ultra polite. There's multiple videos out there that show that I don't think you were ever unprofessional. We were just like, hey, sir, you know, could you possibly do this or check with this person? Or maybe this is a big misunderstanding. And it was always met with, nope, you're going to jail. Nope, you're getting arrested.
Starting point is 00:46:16 I mean, at some point along that process, it became very clear that in regards to any amount of paperwork that we would have had on us or anything that we could have said, there was something else going. on. It wasn't about that. We had the paper where he had like the deputy has already verified, cleared, identified us, but let us go essentially. So despite all that, there were, there was something else going on that regardless of what we could have said, done, or shown, there was no getting out of an arrest at the point. We're both being very professional throughout the entire process. I'm a very big privacy advocate and as we're going through this, what's your marital status, what's your highest level of education? And I'm very understanding at this point we're being wrongfully arrested because we're here for a job. This is something that needs to be drugged through
Starting point is 00:47:02 a criminal process. At most, if there's contract discrepancies, we're issues with the state first county level. This is something that gets handled in a civil courtroom. So at that point, I didn't want to provide my social security numbers. So it's not like we're resisting or arrest or anything like that, but unwilling to give up a lot of personal details at that point, which a lot of people in the book in a reception room, however you want to call it, got very upset with that. So we get, you know, we have to give up all of our tools, all of our gear. We go through the process explaining what these tools are because we're being booked not only for burglary, but possession of burglary tools.
Starting point is 00:47:39 So they want to have substantial evidence of us having tools that are used typically in burglary trade, obviously in a security setting at this point. They finally get to make some phone calls, but at this point, it's like 2 a.m. I had about 30. But unfortunately, everybody was sleeping and no one would answer my call. Even my wife slept through all of the phone calls that I said to all sorts of messages to people. The only person I was able to actually get a hold of was one more contacts.
Starting point is 00:48:06 And I said, hey, are you aware where you got arrested? Yeah, yeah, we're aware such and such told me. Are you doing anything to get us out? And he said, well, yeah, we're going to be there first thing in the morning. We're going to talk to X, Y, and Z. I don't remember if you said we're going to talk to. and we're going to smooth this all over. It's one big misunderstanding.
Starting point is 00:48:25 You know, you'd think that, and I believe almost verbatimus thing, you think that the sheriff would be a little more understanding of what we're trying to do. And I said, well, guess what? He's not. And you said, yeah, I can see that. Again, we'll be their first thing in the morning. We're going to hammer this up.
Starting point is 00:48:40 There's a lot more of that conversation, but that's the jest up. Now, for me, my first call would have been to my boss. I would have called coal fire right away and told them, hey, get some lawyers. We're in jail. We need help right now because they're operating in capacity of coal fire. So coal fire should be capable of helping them out. Yeah, and we tried to get a hold of coal fire.
Starting point is 00:49:00 We just couldn't get a hold of anybody just because of the late hour. And I think most people, when they sleep, they put their car, you know, they put their phone on vibrating. Because, again, we're talking about a scenario that has never happened before. So maybe you want to say some concatency, whatever you want to put in there. Who knows what it was? But most people were like, okay, you know, two or three in the morning. not really nothing of the deal. You know, what's the worst they could happen?
Starting point is 00:49:23 Well, we figured out what the worst thing could happen. By 2.30 a.m., the police finished processing them and give them both orange jumpsuits to change into, the kind you see prisoners wear. And the police took all their belongings, even their shoes. Gary got a pair of crocs, Justin got some sandals that were too small, and they were put in a cell for the night
Starting point is 00:49:44 with other criminals and cellmates. They try to lay down and sleep, but the beds were really high. and cold, so they didn't get much sleep that night. The next day, they had an appointment to see the judge in the very courthouse they broke into. So the officers escort them to the courthouse. When we walked over there in the morning,
Starting point is 00:50:13 although it was incredibly uncomfortable and embarrassing, that we were over there literally shackles around, you know, the whole around your wrists and then tied around your waist, and then the chain that goes from your wrist through your waist all the way to your ankles, and then you're attached to the guy in front of you, you know, and you do the, you do the, what is it, the railroad gang or whatever, across the street with deputies in front of evening back to you. And I was like, you've got to be kidding.
Starting point is 00:50:40 We get over there, and the whole time I'm thinking, we just got to make it to nine in the morning. The state's going to be here. They're going to explain everything. And then the judge is going to be like, this is silly. Like, why are you guys? Go ahead. Show on your own recognizance. You can go home. So they get to the courthouse. They sit down in the courtroom and await their names to be called. by the judge. And it boggles my mind still that this is the very courthouse that they broke into last night and now they're sitting in the courthouse waiting to see the judge. I was first. Yes. And there was a gentleman that was sitting next to the sheriff. The sheriff was
Starting point is 00:51:15 in the gallery, I guess you could say. And there was only one man standing next to him. And so my thought was good. That is the court representative from the state court, right? He's talking to the sheriff. If they've talked about this, they realize this is just a big misunderstanding. Everything's going to be good. They're going to let us go, is what's still playing in my mind. I sit there, I go in front of the judge, and they ask your name and say, what's your name? My name is Gary Di Macario. How much money you make?
Starting point is 00:51:40 I make X amount of money. Who do you work for? I work for a company called coal fire. And so at that point, they decide whether or not you can qualify for a public defenders, right? Public defenders. She says, you do not qualify for a public defender. You know, would you like to defend yourself or would you rather? outside counsel. I'm like, well, I'm hoping outside counsel isn't necessary because, ma'am,
Starting point is 00:52:01 I believe this is just a big misunderstanding. So I launch into my reason why I think this is a misunderstanding. I explained to her what it is that we do, what we were doing that guy, who we work for. And she looks at me and she says, you must think I'm stupid. And at that point, I'm like, oh, Lord, you've got to be kidding me. This is not happening. And she launches into this, I don't know, diatribe, like, just like, I'm the biggest idiot that she has ever seen step in front of her in her entire life. Like, that is not the way that things happen. She is a state in place.
Starting point is 00:52:38 She works for the state. If the state was doing this, she would know about it. And this is not the way that things happen at the state, et cetera, et cetera, et cetera. And I just went from being hopeful to just seeing red. I was just irate. Keep in mind that both Gary and Justin barely slept the night before it. And they're in these orange jumpsuits with shackles on. They aren't presenting themselves as best they could, given the situation.
Starting point is 00:53:06 But when the judge said this to Gary, he couldn't believe it. He stood there, totally shocked. Tons of rebuttals are going through his head. But he wanted to be courteous. So all he could do is stand there and be quiet. But he was thinking things like, You are a judge. You're literally the point of your position is to be able to look at someone
Starting point is 00:53:28 and have some semblance of an idea whether or not that person is telling the truth or not. And the only thing I can think of is you've been dealing with people and liars for so long, you can no longer tell the difference between somebody who is innocent and telling the truth wholeheartedly and somebody who is a liar.
Starting point is 00:53:48 Which obviously he's not saying that to the judge, but that's going through both of the part. Obviously what we're thinking. The judge charged him with burglary and possession of burglary tools. then went on to say a bail is set for $5,000. Justin couldn't believe the judge was saying this either. Same, yeah, I'm like, as not the person on front stage,
Starting point is 00:54:09 but obviously still in the same boat, I'm like, oh, no, there's no way. Like, this is like a bad joke. You've got to be kidding me. Not a chance in hell. This is how this is going down. So I'm just kind of like sitting on the stand in awe. Like my jaw is dropped to the floor, looking at the situation transpire in front of us. So there's still this gentleman sitting next to the sheriff. I'm okay. And I'm like, well,
Starting point is 00:54:33 again, internal monologue, well, ha, Joe, you judge, this guy's from the state and he's going to explain everything. So this guy walks up to text me and says, excuse me, ma'am, I'm the county prosecutor and we think these guys are a flight risk. We would like to increase their bail. And I'm like, oh, Lord, like, are you kidding me? I literally start looking around the courtroom, looking for somebody else. I'm like, where is our state representation? They told us they were going to be here. Where are they? They were nowhere to be found.
Starting point is 00:55:04 They told us they were going to show up. They ghosted us. 100% ghosted us. There was nobody there to defend Justin or Gary. The three contacts on their get-out-of-jail-free card did not come like they said they would. And this was just too soon for anyone from coal-fire to be able to come down and help either. So they were just standing there, completely baffled. irate that this was happening.
Starting point is 00:55:30 And I will say at one point during this exchange, the judge is looking at Gary and she's like, you need to come up with a better story because nobody here is believing this, to which Gary retorts, well, you should talk to the sheriff because the deputies last night had verified us. Everyone believed us until we're here sitting in front of this courtroom. He looks over at the sheriff and the sheriff is just kind of like, he just smiled and shrugged. He didn't say anything.
Starting point is 00:55:56 Again, on our minds, we're like, don't you have some sort of ethical responsibility? to say, actually, ma'am, we did verify with someone that worked for the state. However, we haven't fully confirmed that. Or something of that age. Anything. Not a word. Nothing. What a frustrating situation.
Starting point is 00:56:13 Yes, they broke in the courthouse, but they had 100% permission to do so by the information officer, the director, and the head of infrastructure for the Iowa State Judicial Branch, the very state department that runs these courthouses. And then she read the address of where we broke in. And she realized that it was her court. house in her courtroom. And she was mad. I raped.
Starting point is 00:56:35 She was like, how dare you break into my courthouse and my courtroom at this address? And she just went off. And then she's like, bail is set for $50,000. And our bail originally was a $5,000. Ten times typical. Dale, poor Berger. Yep. And that's just how much bail was set for Gary.
Starting point is 00:56:53 So I go up shortly there at it. I mean, that's pretty much the end of the exchange. I go up. And same deal. I don't believe this. I'm like, well, we were authorized by the state. We're in this testing, like, after seeing what Gary had gone through, I'm like, there's no point.
Starting point is 00:57:04 Like, don't, don't open your mouth and say something that could be potentially incriminating here. So I'm like, oh, okay, like, we're going to do this, I suppose. Gary and I, again, treached back across the street, back in our holding cells, where Gary has cellmates of a wide variety. But one says to him, he's like, man, I can't believe that. You went up there as professional as could be, and she disresolved. respected you. Even the inmates just looked at us,
Starting point is 00:57:36 so they were like, man, you guys are so innocent. They didn't even have to listen to our story. They're like just the way you guys talk and the way you carry yourselves and the way you look, they're like, man, you don't look like you belong here. Like, what are you doing here? Justin's bill was also set for $50,000.
Starting point is 00:57:53 So the way bill works in the U.S. is that you can either sit in jail until your court case, or you can pay this amount to get out of jail and come back for court. At that point, we're facing felony charges. Like, we're facing felony burglary charges and felony possession of burglary tools.
Starting point is 00:58:07 So we're in a criminal trial at that point. And looking at seven years in prison as well. Right. Seven. Right. Still, they hoped any moment their point of context would come and sort everything out. But the situation was becoming less hopeful.
Starting point is 00:58:22 So Gary and Justin got some more phone calls and eventually got Coalfire on the phone and tell them everything. And Coal Fire immediately started working to bail them out and to get help. And so about 20 hours after going to jail, the $100,000 in bail money came through
Starting point is 00:58:37 and they were let go. At this point, it's Thursday, and their return flight is on Saturday. Oh, yeah, coal fire gave us permission to do whatever it takes, get out of that state, like, come back home, boys. Oh, yeah, we booked earlier flights. Both Gary and Justin go back home and get lawyers to help them with this.
Starting point is 00:58:59 Something had gone terribly wrong, but they still weren't sure what. Why was nobody listening to Reason here? Why are they even being blamed for this? This should be a contract dispute, not fall on these two guys. Felony charges? The local news ran a story. Two men arrested for breaking into the Dallas County Courthouse
Starting point is 00:59:18 say they were hired to do it by the state. Justin Wynne and Gary Dermerkrio are both now charged with third-degree burglary and possession of burglary tools. They were taken into custody around 1230, and the name warning. As KCCI's Alex Schumann shows us now, the men say they were doing cyber security work. The state court administration says they did hire this company to test the security of their electronic records, but did not intend for them to physically break into the courthouse. Not many had yet heard what happened. But once they learned, people had plenty of opinion. They needed to be rested. You're going to try to break in.
Starting point is 00:59:56 Period. Lock them up. They're a way key. I don't care. Well, that bystandard they interviewed, I guess, didn't like them for some reason. But you might have caught in this news clip where they said the judicial branch did not intend for these two to break in. Well, the next few months of this ordeal were painful and grueling for many people involved. The news reports I read said they interviewed the state judicial branch who claimed that they didn't know a physical assessment was going to happen. But then coal fire outlined in the contract to show them that a physical assessment was approved. So then the state changed their mind and said, well, yeah, we knew that was happening, but this was happening outside the hours described in the contract.
Starting point is 01:00:37 But then Coalfire said, we left a calling card on your desk overnight, and you emailed us saying, congratulations. Why didn't you tell us to stop then? The state went on to say, okay, sure, but we didn't know you're going to break into courthouses. But yet again, Coalfire showed them the contract and showed them the exact locations of the addresses of each building intended to be tested, which included. a few courthouses. Eventually, the state judicial branch
Starting point is 01:01:04 ran out of fingers for pointing at coal fire as the problem. But while that certainly fanned the flames of this problem, it wasn't the main fuel source. See, this was a county courthouse, and it was a state department that
Starting point is 01:01:20 hired them. State and county are two different things, so the sheriff, judge, and county prosecutor were sticking with the story that the state had no author to conduct a physical penetration test on this building. This was the main crux of the issue. And if the county was not aware that this was going on,
Starting point is 01:01:40 then they had to assume that Gary and Justin were actual criminals. If the state had no authorization to conduct these tests on this building, then it would be the same as if that gas station attendant across the street sort of paid them to go break in the building. So from the prosecutor's perspective, they thought these two guys were actual criminals. Well, so here's the caveat is after all this was set and done and we were bailed out, the state ordered a third-party investigation into this scenario. There was a lawyer, well, a law firm that performed the investigation.
Starting point is 01:02:17 The final findings, which are public, the very end of those findings, that lawyer is looking at some sort of precedence, right? All laws based on a case before, right? That's where you get your legal precedence. Well, what was the, in a similar scenario, what was the judge? So because this has very little precedent associated with this, it's up for interpretation of the law. During this third-party investigation, that lawyer's interpretation of the law was the state had legal authority to authorize a test on county property because they are tenants of that property. It's their authority to protect that warehouse and administer security for it. Right, and the things within that court.
Starting point is 01:03:00 Right. The prosecutors held their position. They started looking through the contracts to try to find anything that wasn't right. Justin and Gary both went back to work for coal fire during all this, but they weren't able to really focus that well. I mean, for one, they had long talks with lawyers and going over tons of evidence and documents with them. And this is hard to find time to do when you're typically spending a week at a client's site doing a penetration test. And this news made its way around. So if Gary or Justin got on a call
Starting point is 01:03:33 with a client to do a pen test, some clients wanted to hear the whole story about what happened in Iowa. And so it was just really distracting. And of course, they were arrested with felony charges. So like some clients have sensitive buildings and they do background checks on the penetration testers. But with felony charges, they weren't able to do these assignments. So they spent months battling this out with the prosecutors. And a lot of what I know about this story was through documents published by the Iowa state courts. There was some great journalism work by Arstecna, which got a lot of the documents and posted them publicly. And here is where I see the rules of engagements and the positions that the state took on various things and how they broke into
Starting point is 01:04:14 different buildings. In fact, somebody even interviewed the Iowa senators to see what they had to say about this. Senator Amy Sinclair said, quote, the hiring of an outlawful. company to break into the courthouse in September created significant danger, not only to the contractors, but to local law enforcement and members of the public, end quote. And also Senator Zach Whiting had something to say. He said, quote, essentially a branch of government has contracted with a company to commit crimes, and this is very troubling. I want to find out who needs to be held accountable for this and how we can do that, end quote. So eventually, when the third party investigation was complete, which said that the state had jurisdiction to hire a coal fire to run
Starting point is 01:04:55 these tests. And the state point of context all approved that coal fire was hired to do it. All this came together and was given to the county prosecutor. So all that comes to light and eventually, I think it was a month after the county had the opportunity to either drop charges or to continue press in charges, at which point they decided, okay, felony charges aren't really relevant here, but we're going to drop this down to misdemeanor trespassing charges, which I think they expected us to immediately say, yep, yep, we're guilty, we'll take that, which of course from our perspective,
Starting point is 01:05:28 we're legally hired for this job. Like, no chance in hell we're going to plead guilty to misdemeanor trespassing charges, even though it's essentially a traffic ticket violation or something similar at that point. We weren't going to go along with that. So we're still fighting that. And that fight took place over the next four months.
Starting point is 01:05:46 All sorts of fights between our lawyer and the prosecutor. Oh, constant. To even get to the point where the prosecutor is like, okay, well, maybe we'll, maybe we'll drop it down to criminal trespass. Our lawyer was like, look, man, in order for there to be burglary, they have to have criminal intent to commit a felony after entry. These guys were working. There is no way that you can prove criminal intent. And so they did everything in their power. They're like, well, if they dropped a key logger on one of the systems, then we might be able true. I mean, they were, they were grasping at straws to do anything and everything in their power
Starting point is 01:06:23 to try to hopefully make that stick for some reason. And they knew at that point. They knew we were under contract. They knew that we were asked by the state to be in that courthouse. And they still were pushing for these felony charges. And these classy felony charges was seven years of prison time behind it for, I don't even, I still do this day, have no idea why they kept pushing so hard for this stuff. Eventually, the Dallas County prosecutors in Iowa came to an understanding, and on January 30th, 2020, they dropped all charges against Gary and Justin. The case is now over, and they're free men once again. But what still lingers is their criminal record still shows that they were arrested for burglary and we're given felony charges. So that's kind of like why we're upset at this point.
Starting point is 01:07:20 Like we're going to kill the rest for our lives. Like we have felony arrest records. Like even though charges are dismissed, like everything's been dropped at this point, anytime we get pulled over. If we ever try to apply for a job in the future, security clearances in any number of things, volunteer work. It's going to show we've been arrested on felony charges. So we've been stripped of rights with no due process on wrongful arrests. Yeah. It's a shame. Like any traffic stops these guys get, when the police look up their record,
Starting point is 01:07:47 it's going to show that they were once arrested with felony charges. And any time in the future, where they're on a physical assessment, and the cops come, they'll see that they have burglary charges on their record, which might make the cops think, like, yeah, these are real burglars. Look it, they have real charges.
Starting point is 01:08:02 And any background checks that someone does on these two is going to show their criminal history? And, I mean, what do you write when you're applying for a job and it asks you, have you ever been arrested? Like, what do you put? yes, but it was wrongful, it doesn't sound fair to me. Big things, little things, like, just, it just affected our lives for the last six months. And honestly, like, still will continue to do.
Starting point is 01:08:26 Like, yeah, what the rest charges, but man, just like, honestly, I know a lot of people, like say a lot of stuff, oh, you know, damages. I'm so stressed out over this and they want to do, like, a counter lawsuit. Like, no, like, I think my physical brain chemistry has changed over this being so stressed out. And, like, I sound like a wimp about it, but man, like, you wouldn't believe it until you're and going through something like this, how stressful and traumatic.
Starting point is 01:08:47 I don't even want to use that term of settle. But it is, like a traumatic experience to go through something like this and have it held over your head for such a long time when you know you're on the right. And then to see the legal system fail you repeatedly, there were so many opportunities and avenues
Starting point is 01:09:03 for the county to understand or get more information and then drop the charges and it just never happened. And I think that was the, that's the biggest detractor from all of this And the point that was so aggravating is so many times everybody had every opportunity to do the right thing. And they just continually didn't.
Starting point is 01:09:23 It was just, it was like, for the lack of a better term, it was like, I was flabbergasted. Like to old school, right? It is just how can you, how can you do this to someone? You know, you know that we weren't there doing anything malicious. You know we weren't actually breaking in to do. to create some sort of crime or to have some sort of crime. You know we were there doing our job.
Starting point is 01:09:49 Why are you still pushing seven years of prison time? Why are you still pushing us? And it's like they had absolutely no mindset for like lack of a better term or maybe it is the best term. Like destroying two professionals
Starting point is 01:10:04 who have absolutely sparkling clean records who've never even been in trouble for jaywalking before. And they're just, It's like, oh, no, yeah, no big deal. You know, we'll just keep throwing these, these class C felony charges at them. Yeah, you know, if we drop it later, you know, whatever.
Starting point is 01:10:21 It doesn't affect us. It doesn't harm us. What do we care? And just, just like the, I want to say, the lack of sympathy or anything or professional or whatever term you want to throw there just for, like, just, and not even bust, but just another human being. It's right. Like, if you're representing the law, it's a failure.
Starting point is 01:10:43 of the legal system, which I had no idea America worked that way. It's like just not the America that I was brought up. And I thought, like, innocent until proving guilty and just to see us stripped of so many rights and they go through this, it was just such an awkward experience to be, like, thrown into this mix. It was terrible.
Starting point is 01:10:58 And that was the hardest part was watching people do the wrong thing repeatedly and thinking it was not a big deal. Because to them it wasn't. The only big deal was to us, but no one seemed to care. And that is where we left off back in 2020. when this episode first aired,
Starting point is 01:11:15 they were arrested but fought it and got their charges dropped. That should be the end of the story, right? Well, no, there's more, lots more. First was the response from the information security community. They were outraged from this. This jeopardizes a whole industry. People who have gone to college to get degrees in this
Starting point is 01:11:33 are now seeing like, wait, you can get arrested for this, get felony charges and be facing seven years in prison? What the heck? So 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. I interviewed John Strand for an episode before. It's called The Big House, where he sent his mom to do a penetration test for him once.
Starting point is 01:11:55 And a few weeks ago, I ran into him at DefCon and asked him what his response to this was. Sorry for the background noise. DefCon is a busy place. After that news hit, what did you do? We immediately went to the town of Adele, Iowa, and we did AwarenessCon. and we invited the entire community to come down and ask the security community questions about what we did. Yeah, and because John Strand is the founder of Black Hills Infosec,
Starting point is 01:12:22 he knows a lot of people in the industry, and he rounded up some big names in cybersecurity. Dave Kennedy, Deviant, Jake Williams, all of which have been on this show before, they all went and gave talks in Iowa, because obviously the people there had no idea physical penetration testing was even a thing. And you heard that one.
Starting point is 01:12:41 guy earlier in the news interview. He's like, these guys should be locked up. If ignorance of the law is no excuse when you're caught breaking one, then what about the reverse? If the sheriff, the judge, or the townspeople are ignorant that this is a profession, then should that be no excuse to demonize these two? But John Strand thought he's going to do what he can to educate the people in that town. To teach them all of this is legitimate. There is a whole industry of people doing this, there are professional conferences, degrees, books, certifications that you can get to do
Starting point is 01:13:16 this. It's absolutely wonderful. The sheriff, Leonard, he came and he talked. Here's that clip from AwarenessCon, where the sheriff came to give his opinion of this whole thing. I'm a very, very happy Sheriff Leonard has shown up, and I asked him how he wanted me to
Starting point is 01:13:32 introduce him to the group, and I'm not joking. He said, you can introduce me as the bad guy. So, he has a great sense of humor. So everybody, could you please give a round of applause for Sheriff Flannes? Well, first off, I'm sorry. I'm obviously the reason you're all here.
Starting point is 01:13:51 But I wanted to stop here and tell you that I have a lot of friends that do this for a living too. And with Homeland Security and all those type of things and nothing but supportive of the industry. And it's not, there's just a whole lot of things that went into this that night that we're still in question. So, you know, and I think I was talking earlier, getting a lot of hate mail and a lot of stuff from the industry worldwide. I mean, London, everywhere. You're just getting how dare I do this. And, you know, you got to look at it from law enforcement perspective for what we're responding to. You know, if you're telling me that this is a, we're just checking your response time.
Starting point is 01:14:34 And I had five deputies running 140 miles an hour to get there. That doesn't work well because of. If one of your family members was teaboned by a deputy, you'd be mad, especially when you found out it was a fake call or something like that. That common sense, that's bad business. You know, if somebody would have got killed on the road that night, those type of things. So, I mean, we just need to work better together. I don't know if this is a common thing, if this is all, you know, but there's a lot of things that we got to look at. The only reason, and the other thing, those of you that do the job, I would never charge you with the crime and let it continue.
Starting point is 01:15:06 I don't have the ability to dismiss it, but I can work with the case. county attorney and those type of things. But at the end of the day, if we believe that you truly needs to go away, it will go away. But I guess I just wanted to stop and let you guys know that we do appreciate you and what you're doing. And it is a needed. What you do is very needed. I couldn't do it. I don't know how to do this stuff.
Starting point is 01:15:29 And I rely on you folks to help us. And the two gentlemen that night, they're good guys. But you got to understand that when you come here and rural Iowa, from Florida, you're from Seattle, Washington. Chances of you coming back when I ask you to come back to answer questions, or slim to none, I promise you that. So we just, you know, I just met you. So you're not going to, there's a whole lot of questions that go into these things
Starting point is 01:15:53 in the middle of the night that we have to put all that together. So I just wanted to stop and tell you that there is no friction between, as far as I'm concerned, between us, just asking that you kind of wait for it. We're not out to prosecute anybody. I would never charge any one of you with the crime if I didn't think it was valid. And if it's proven down the road and if we get through this investigation with all these other agencies and it needs to go away, I'll advocate for it to go away. I wouldn't want any one of you to have a criminal history that you didn't deserve.
Starting point is 01:16:27 So if I could recommend anything, it would be work with your local law enforcement when you're doing it. I would have helped. If I would have known about it, I'd have helped you do it. you know, I would help them accomplish their mission, you know, that night. So, and we wouldn't have any of this problems. So, but anyway. I think Awareness Khan did, in fact, change the hearts and minds of those living in Iowa. Because after that, there was much more support for these two penetration testers who got arrested.
Starting point is 01:16:56 They were starting to come around and feel sorry for them. Some were even saying, please don't judge Iowa based on this. And so, while I was at DefCon, I wrote. ran into those two penetration testers from this Iowa County Cornhouse story. And it's now been six years since this happened. And we last spoke. So I wanted to get together with them and find a spot at DefCon and sit down and hear what's new. So you got arrested, brought your charges, got the charges dropped.
Starting point is 01:17:24 Story's over, right? There's anything else happened since then? A couple things. What's new with you? I mean, so have you ever heard that thing where you go to prison and you turn gay? Yeah, no, I'm not gay, but definitely turn into a girl. Gary has changed her name to Gabby. Well, it's my handle.
Starting point is 01:17:45 I just, I guess, absorbed the handle, Gabby, yeah, because I can like to be anyone I want to be. You got your charges dropped. So after charges are dropped, are you like, I'm good? Like, I can finally go back to my life. Everything is fine. I don't feel like it was like that at all because there was so many things that said that just were not accurate or just outward lies. Fabrications like changing the narrative and it just to say like, oh, cool, we're innocent. Well, no shit.
Starting point is 01:18:19 Like obviously we're innocent the entire time, which is why we never settled for anything the entire time. And so them dropping it would almost be like them doing us. favor, which was not the case. And they did themselves no favors by dropping it other than embarrassing themselves further. Like, that was for them, definitely not for us. What more can you do after charges are dropped? That's part of the judicial system that's messed up is you're guilty until proven innocent. You spend time in jail. You get your name drug through the mud. They lie about everything. And there's zero repercussions unless you go after them, like, for a personal suit.
Starting point is 01:18:56 A personal lawsuit. Is that possible? Can you sue for wrongful arrest? They felt like something seriously unjust happened to them, and they wanted to do something to make it right. I think Gabby was already thinking about it. You look at her mugshot, smiling in there. She was already thinking about the lawsuit as soon as the cuffs went on.
Starting point is 01:19:17 Pretty much. You were in the jail cell saying, as soon as I get out of here, I'm going to sue these guys. Because I knew we had done the... We were the most cooperative, at least one of us was for 99% of the time. The other was 100%. But, again, you had nothing wrong with what you did. They were being super invasive.
Starting point is 01:19:40 No, I don't trust them. Give me my information. I saw how they secure things. But that was, like, it's a good learning point, right? Because we did nothing wrong. We're going to be completely cooperative. We're going to do everything. And then you do everything, right?
Starting point is 01:19:52 And then they just lie about stuff to try to cover their own. and try to make it look like they didn't do anything wrong. And you're like, wait a minute. Like, I was truthful. I was honest. I cooperated with you guys. And then you turn around and you completely spin the narrative so you don't get in trouble or you don't look bad or to save your job or whatever it is. And so like not cooperating to me like sounds like the right choice after going through that. Suing the sheriff felt like the right choice for them. Making him pay for the wrongs that he's caused, expose the errors in his ways, make him the guilty one. But to conduct a lawsuit such as this, it was going to cost a lot of time and a lot of money.
Starting point is 01:20:31 We actually had our original lawyer, and we asked him. I think we would really like to go after the county and the state and the sheriff because, like, people need to know that this is not okay. Like, they just can't get away with stuff like this. And he had a real, like, he was afraid to do it, like, for lack of a better term, because he's like, this is a small town. and Iowa's not big. Everybody knows who I am,
Starting point is 01:20:56 and I feel like if I go after the county and the state, in the sheriff and all these lawmakers, especially after they had that investigation, and he's like, I don't know that that would be great for my career at all. So their lawyer made a few phone calls and found them another lawyer named Marty who was just about to retire.
Starting point is 01:21:14 And he's a civil rights lawyer, and he loved the case, and he's like, I will take it on, I'll do a pro bono. He's like, I've made my money. Like, I am literally, he's literally at the Twilight's career. He extended his career to finish this case. So they got a new lawyer, and they wanted to sue the sheriff, the prosecutor, the judge, all these people who treated them bad.
Starting point is 01:21:34 But this is where Gabby and Justin started learning some new words. Words like... Qualified immunity? And sovereign immunity. See, qualified immunity means you can't sue government workers, especially judges, prosecutors, and cops. They're shielded by the government itself. so they can't sue the actual people who did them wrong, who made these mistakes.
Starting point is 01:22:00 And then there's sovereign immunity, which means you can't sue the government unless the government agrees to be sued. Well, we tried to go after the state, and it's very convoluted because the state is the one that passes judgment on whether or not the state is guilty or not. So it's like somebody coming to you and saying, we're going to sue you, are you guilty?
Starting point is 01:22:28 And you're like, of course I'm not. They're like, oh, sorry, I can't see you now because you said I'm not guilty. So the state immediately threw it out. They tried to make this a federal case to sue the state. Since the state wouldn't pick it up, maybe the federal government could oversee it and decide. It got picked up by a federal court.
Starting point is 01:22:44 But then when they looked at it, they just kicked it back down to the state who just closed it right away. So it's just like they tried so hard to stack the deck against us at the, like, at every single turn just to make it where it was not going to be, or didn't feel like it was impartial at all through the entire process. Like every step that they could take to stack the deck in their favor, they absolutely tried to do it. Absolutely did. So this lawsuit they wanted to wage was dead in the water before it even got a chance to
Starting point is 01:23:15 begin, which is really frustrating because what mechanism can you even use here to bring justice to a situation like this? So we were left with the county and the sheriff. And so even though the sheriff has qualified immunity, or the prosecutor is the one, the prosecutor is the one that has qualified immunity, the sheriff has some protections but not complete. And so we had to go through the process of saying,
Starting point is 01:23:41 these are all the things that we think he did wrong. And then the judge said, yes, yes, no, no, no. And then we were eventually left with what the lawsuit ended up. And so they said there is enough evidence to show that the sheriff did do these things wrong. So we were able to go after the sheriff, but we went after the sheriff's position, not Chad Leonard, the person.
Starting point is 01:24:01 So we had to go after the actual sheriff, which means he's also covered by the county's insurance policy, and nothing, like not one cent comes out of his pocket, he doesn't get reprimand, like nothing. Absolutely nothing happens to me. It's a moral victory at best. Okay, so they started a single lawsuit that got accepted in the courts against the,
Starting point is 01:24:21 the county and the sheriff's position. Finally, this thing was starting to get some traction. And this felt like progress, since Justin and Gabby really wanted to use the system to seek justice of everything that went wrong. My question is, what were you hoping to get out of the lawsuit? $1.1? That was all I cared about.
Starting point is 01:24:38 I told Marty. I was like, as long as I can drag this dude through the mud like he did with us, except with facts instead of stories, like that's all I care about, which is the entire time, which is why we were like, They were like, you should, you should just take the trespassing charge and nope, nope, nope, like the entire time. My entire goal was just to show that this, like show this person for who he really was, which is just a lying corrupt individual.
Starting point is 01:25:07 Dang, this is getting pretty good. They got a lawyer who's all in, retired, working for free, doesn't care about what people think of him anymore. Gabby's just coming out with claws out. This is going to be a good fight. and they eventually decided to ask for more than a dollar. They wanted this to hurt, and they also wanted to cause panic and fear within the county. And they also wanted the townspeople to see what happens when you elect a corrupt sheriff? We submitted the maximum amount that the insurance company would have covered for the county,
Starting point is 01:25:35 so we didn't want taxpayers having a front more money for having a poorly elected sheriff. So yeah, that's the dollar amount that we set. And I think the other part of it, too, that's really important what we wanted out of the case was to set new precedent that this is okay. You can't put hackers in jail and try to prosecute them when you hire them to help defend you. So they were now seeking quite a bit of money from this lawsuit. I'm not sure exactly how much. They wouldn't tell me.
Starting point is 01:25:59 My guess is that they wanted to split a million dollars. Keep in mind they already paid $50,000 each just to get out on bail, and then they spent the night in jail and they were threatened with seven years of prison that they had to fight tooth and nail to get that charge dropped. And those lawyer fees added up, too, of course. That's a lot of stress, real costs and anguish that they had. to go through. So to split a million dollars, I think that sounds reasonable for the amount of hardship they endured. But Gabby was still furious from this whole ordeal.
Starting point is 01:26:27 Like World War II, what's the saying? They woke the sleeping giant. Like Japan thought if they came in and they smashed us that we would back off and just slink away and not do anything. Kind of the same thing here where we just throw a weight around and we threaten these guys with six years in prison and all this other stuff. They'll just take the deal and they'll go away. And that was not the case. Like, we don't fuck up. Like, Justin and I, we do things by the letter, by the contract. Like, everything we do is meticulously perfect for that reason, because, like, of what we do, we don't want to mess up. And I think all that, this whole thing just showed that and highlighted it, because if we had done something wrong, they would have found it.
Starting point is 01:27:06 And they were unable to. And so now, five years later, the tables had turned, and we had all the evidence. We had all the data. We had the video cameras. And we had the recordings. And We had everything, and then it was the exact opposite, where the county and the state was like, oh, shit, they've got everything, and we literally have nothing except a really, really bad arrest from a corrupt individual. Together, they had collected tons of evidence supporting their case, and they were feeding it to the court, and the county was starting to sweat a little. And despite how confident Gabby felt that they would win this case, it's still a scary thing to go up against. the government. I mean, they could drag this case on for years and exhaust you and run you dry of money and energy only to ultimately drop the case or reject it due to some clerical error, making the entire process pointless. Years of your life can be wasted in a process like this,
Starting point is 01:28:03 and the government just doesn't care, and they do these kind of things fairly regularly too. They use the process as the punishment. The stress of courts and judges and charges weighs heavy on a person, like really heavy, and they know that. So even though they knew they probably couldn't even win that original criminal case against them, they still wanted to use those charges as a form of punishment. So fighting back at the government like this is the story of David and Goliath. Not only were these two penetration testers the first ever to be wrongfully arrested for penetration testing, but they're also the first two to ever sue the government to protect their rights as penetration.
Starting point is 01:28:44 testers. This is an epic story. This case could set a precedent. And it was just the right thing to do. I think we didn't have a choice. I mean, to have our countersuit back at them. I mean, that was the only way to try to restore any sliffer of justice around our case in that state. So in our minds, Damning Cross it. Just no-brainer, had to sue back. But the funny, David and Goliath, I think that's hackers, right? is like the power that one individual can hold. That's why governments can be so scared of these individuals. You can do a lot even as a single person.
Starting point is 01:29:16 So against the government, it is a mighty entity. But still, again, that's kind of for a lawyer to handle. It's all about the information. And we had all of it. He felt like he had no choice. And that was the right thing to do. Wow, those are some powerful words. This is what patriotism looks like in practice.
Starting point is 01:29:35 To put the government in check when it overreaches and force it. So how does the county react to this? Of course, they delay it. The original court date was supposed to be in 2020, but that got delayed, canceled, pushed back again and again. The county tried to distance themselves from this in every way possible. They tried to slither out of it, hoping that Justin and Gabby would grow tired or forget about this or just give up. The further they could get away from the moment, the better for them because they wanted it to fall out.
Starting point is 01:30:06 They didn't want people to bring it back up. So year one goes by. Very little happens. Basically, they spent the whole year just opening the case. Year two goes by. Nothing happens at all. Year three, they just keep delaying things, keep pushing it back. And this is really starting to test Justin and Gabby's patients.
Starting point is 01:30:23 Like, come on, we've presented all the evidence to you. Why are you not looking at this case and trying to get it closed? Also, at some point during all that, Chad Leonard, the sheriff that they were upset with, retired and moved out of state entirely. So whatever outcome this law, It's going to have. It's not going to bother him at all because he's just relaxing in some Florida community somewhere now. But their lawsuit was with the sheriff's position, not the sheriff himself. So the case continued around this time to Justin and Gabby's relationship with coal fire started to sour. They didn't feel like they were getting paid enough or treated right by them. The first year after we got arrested, we had over $5 million come in directly for people saying, hey, we want to work with Gary and Justin. And we want to. work with the Iowa team and blah, blah, blah.
Starting point is 01:31:10 I don't care. Our story was one of the most valuable things that happened to Coalfire. Even the CEO recognized it's like, yeah, the number one reason Coal Fire is known is because of this case. It is funny. If we ever talked to anybody and would mention, oh, you work at Coalfire, like, oh, man, you ever hear that crazy story? Those guys that got arrested?
Starting point is 01:31:26 I'm like, no, tell me about that. Gabby quit her job at Coalfire and went to apply at other places. I didn't quite get the full picture. Is Coal Fire good or bad? individuals in coal fire are very bad. I think coal fire as an entity during that time was good. She was able to quickly get interviews at other places, but even though she was the best for her job and the most qualified,
Starting point is 01:31:52 her reputation from this case alone made people turn her down. She had a hard time finding another penetration testing job because of this story with the Iowa courthouse. She took six months off just to clear her head and relax. Like really started coming in question like, damn, am I even going to be able to keep doing this because of what happened? Great opportunity to start your own business then and do it on your own terms. Yeah. Yeah. Justin and I had actually talked about it multiple times in the past about starting something different and doing things a little bit differently and treating. Starting something new yourself.
Starting point is 01:32:24 Yeah. And just building a company that treats people the way that we thought they should be treated. We had a vision of we wanted to do things a little bit differently. And so we did that with Kaiju. And thus, Kaiju Security was born, a fresh new penetration testing company based near Seattle, Washington. Adversarial simulation offensive security, yeah. Gabby started it with another guy named Marcus, and Justin moved onto the team shortly after it was formed. And after getting this new company started up, the lawsuit was finally making some movement in year five. Here recently in 2025, you know, it was about showtime. So then we started getting hot and heavy with it, doing depositions, getting things on record,
Starting point is 01:33:05 getting prepped for the trial case. So we were definitely shaping up. You had to go show up in court. And it was, again, going back to the hacker community. We had some great people like DeVient and Drew Porter that agreed to testify in our case just as expert witnesses. So, yeah, we're going through. We really thought we were going to end up in court. We started getting presented with options to settle pretty quickly. I mean, they wait to the last minute with everything like that. And they were throwing out lowball numbers. I think they had like just about like our, Our bond or bail is what they first wanted to offer for like 50,000. Okay, so the county didn't want to go to trial and did want to settle this, but their offer was for $50,000 each. The amount that they paid to get out on bail,
Starting point is 01:33:51 $50,000 each, that doesn't even cover their lawyer fees that they spent trying to clear their names. What an insult. So no, of course, they didn't take $50,000 each. They needed more. So we ended up going through arbitration where they take a former judge and goes back and forth and tries to settle the case. But at that time, they were still being super, super, super stingy, and they were like, oh, we'll give them 50.
Starting point is 01:34:13 And then so the judge, TLDR, the judge comes by to us and through the entire process that took all day long, comes to us and goes, I don't think in my entire career I've ever seen a case so clear cut as this. This isn't a matter of if you win. This is a matter of how much money you're going to get. So I'm going to go back and I'm going to beat these guys up pretty good. he leaves. And Marty looks at us and is like, I've been doing this for 50 years or something like
Starting point is 01:34:41 that or 42 years. He's like, I've never heard an arbitrator say that, ever. I've never, not only had he never heard it, he'd never heard of anyone else saying that an arbitrator had said that. So that was the point I think that our confidence started to go like this, because he had seen, he had seen all of our, everything that we had. And he was just like, yeah, no, this isn't, I don't think this is up for debate. But even with that, the county stayed silent. Instead, they set a trial date, which was three months away, again, making them wait more. So they prepared for trial. They spent an enormous amount of time and energy to gather their materials, find body cam footage, get testimonies and depositions, and bring in expert witnesses. They even took time off work
Starting point is 01:35:29 to go attend this trial. And they booked their flights and their tickets, and they were ready to go. And let me just emphasize what the odds are in this situation. Over 95% of wrongful arrest lawsuits are thrown out due to qualified immunity. Of the few that make it through, 95% of those usually get closed with a $0 settlement or the government wins at trial. For them to receive more than $50,000 from this lawsuit, it's about the same odds as hitting the lottery. It's extremely rare to sue the government over wrongful arrest and win a substantial amount of money. And usually in those situations, it's because the person was in jail for weeks or months under the wrongful arrest. So it's even more rare for someone to spend just one night in jail
Starting point is 01:36:12 and get a large settlement offer. In those situations, you would have to prove, without a doubt, the government conducted an egregious violation, which is what Justin and Gabby was saying happened. But then, a few days before the trial was due to begin, in February 26, they got a number of new settlement offer from the county. The county was offering them $600,000 total, $300,000 for each of them. And this was actually the lowest that they would accept. So they took it. And the lawsuit was closed.
Starting point is 01:36:50 They got paid. They won. And this allowed them to celebrate. Still, I think the biggest one for the community is now we have better precedent, right? So before we were just arrested, fell in new charges. Okay, cops can just arrest pen testers doing their job and try to put them in prison for seven years. But now we can look back. And if that's ever happening in real time to other testers out there, hey, sir, let's just take this slow, take your time, fully cooperative.
Starting point is 01:37:16 But if you want to research, this has happened before. And it's probably not a good idea to try to prosecute or put me in jail for doing my job. Look what happens. Or, you know, the county could have to pay out. Yeah. So really good to have the win under our belt for the community. Everybody else, yeah. I'm obviously much more selfish than Justin's.
Starting point is 01:37:33 And now, finally, they can go back to their normal lives, feeling like justice has been restored in the best way it possibly can be. And now they're focusing on building kaiju security, all with a new feather in their cap. I love saying that, too, because I fought the law and the law won. No, the law fought us, and we won. A big thank you to Justin Wayne and Gabby DiMecchio for reaching out and finding the time to share this story with us.
Starting point is 01:38:07 I really like these two, and I look forward to the next time I meet them. Hey, I just launched a new show. It's called Lo. It's a five-part series. It's the most crazy story I've ever heard. And right now, it's hidden within the Darknet Diaries Premium Feed. If you want to listen to it early, please go to plus.darknetdiaries.com. Otherwise, you're going to have to wait for the public release, which is coming later this month.
Starting point is 01:38:32 This show is created by me, Pony Pie, Jack Re Cider, mixing by proximity sound, and our theme music is by the mysterious breakmaster cylinder. There's an option in WhatsApp, and I can never figure out. Is it Markaz Red or Markaz Read? This is Darknet Diaries.

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