Transcription performed by LeahTranscribesJACK: 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, and 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 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.
DAD: Okay, so, anytime I get a photo or if I want to save it, there’s like three little dots top-right corner.
JACK: Yeah.
DAD: Like saving a photo. I hit the dots ‘cause I want it to save a photo. It used to say Save. Now it says Save to Account. So, I’m clicking on that, Save to Account, but the account is something called OneDrive. Oh, it says Add Account. How do I add an account? ‘Cause OneDrive I don’t use. I don’t even know what that is. This is ridiculous.
JACK: Yeah, where’d you get this tablet?
DAD: You gave it to me. It’s like, all of a sudden my photo — Save Image is gone.
JACK: Where did you get the photo?
DAD: Well, I just pulled up any one so I could explain to you it.
JACK: Okay, so, you took the photo.
DAD: I took it on the tablet.
JACK: [To audience] Did I hear that right? He took a photo on his iPad of 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…
DAD: Oh, wait a minute. No, I found it pushing buttons.
JACK: Good.
DAD: You did it again. I’m gonna go to Photos and see if it’s there. Yep. Okay.
JACK: Awesome.
DAD: I’m not really sure what the sequence is, in a nutshell. You’ve figured it out for me.
JACK: Good work. [To audience] There you go. He figures it out all on his own without any help from me at all. I’m just listening to the problem. That’s how a lot of these calls go. He just figures it out over time and then thanks me. Now, as much as I hate handling these calls because they’re 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. There was another call a few days ago where he got a new doctor, and the doctor wanted him to fill out a twenty-five-page form of all his medical history and stuff. While he was filling it out, he couldn’t figure out how to send the form to his doctor. So, he called me up.
DAD: So, do I hit the X and go to Inbox and then just forward that?
JACK: Yeah, you could send it to them in an e-mail attachment.
DAD: Okay then. I’m gonna hit the X on this patient form.
JACK: What patient form are you looking at?
DAD: The one that they sent me.
JACK: The one you filled out?
DAD: Yeah.
JACK: And it has…?
DAD: Yeah. [Crosstalk] Now I went to my e-mail.
JACK: Does the patient form have all the stuff you typed into it?
DAD: The one I typed into; yes.
JACK: Okay, so it’s got your data on there, and when you hit X, did it ask you to save it?
DAD: Okay, stop, stop, stop. I just wanted to — where I sent it to myself, and there’s nothing on it. Holy cripes. No, I’m not in this…
JACK: Yeah, that’s why I’m asking you if it saved it. So, can you open the form again and see if your stuff is still there?
DAD: No, it’s all gone. How is it all…? Oh, you gotta push Save, probably. All the stuff, you know?
JACK: Yeah, that’s one option. [To audience] This call was particularly maddening. He was so frustrated that he lost all this data from filling out a twenty-five-page form.
DAD: It doesn’t say anywhere on here Save. I’m looking at the new form they sent me, all frickin’ twenty-five pages, and nowhere does it say Save and Send.
JACK: Okay. You know the — one option is to just go down to their office and say, give me the form; I’ll fill it out right here.
DAD: Oh, now I gotta go get ink and I gotta print that — I gotta fill this out here. I can’t do an hour doctor’s office…
JACK: Well, you got nothing else to do today.
DAD: The prescriptions, when did you have surgery — oh, my goodness. Unbelievable.
JACK: Oh, my gosh.
DAD: I know, I should have called you before.
JACK: 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 ten minutes of trying to connect to his home computer, I finally asked him…
DAD: Modify one item…
JACK: No, you’re not — is this all on your iPad or is this on your home computer?
DAD: No, this is on the iPad.
JACK: Oh, I didn’t know that. I thought I was connecting to your computer. That’s why I was using…
DAD: Oh, no. The big computer doesn’t work.
JACK: If I would have known this from the get go I would have been trying a whole different set of instructions. Oi, oi, oi. Oh, man. Okay.
DAD: The big computer doesn’t work.
JACK: 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. 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 to the modern world like this? He’s been using a computer every day of his life since the nineties, 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 is ignorance just no excuse anymore?
Intro: [Intro music] These are true stories from the dark side of the internet. I’m Jack Rhysider. This is Darknet Diaries.
JACK: Okay, this is the epic story of those penetration testers who broke into the Iowa County Courthouse. 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 gonna replay the original episode right now, and then in the last twenty 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. Alright, let’s go. Alright, so let’s jump in and meet our guests for this episode.
JUSTIN: 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, physical exploits to gain access to facilities.
GARY: Yeah, my name is Gary DeMercurio, and pretty much mirror everything Justin said, except I’m a managing senior and I run the Bellevue office in Washington.
JACK: I know they said it quickly, but the important part here is that they’re both penetration testers.
GARY: I’ve been at Coalfire for six years and I’ve probably been in the military another three. So, I’ve got about nine years of experience of physical pen testing.
JUSTIN: Right. I’ve been with Coalfire for over four years, so physical penetration testing for over four years.
JACK: They’ve come here today to share some penetration testing stories with us. Now, even though these two live on opposite corners of the US, one Florida, one Washington State, they team up together on assignments all over the US. The assignment is typically like this; a company will call up Coalfire, the company that Justin and Gary work for, and ask for a security assessment. They might want someone to test their website to see if it’s secure or do a password assessment to see how strong the users’ passwords in the network are, or conduct some compliance checks. This is all to make the company more secure. [Music] The Iowa Judicial Branch is a state department of Iowa. It’s a government facility, and specifically they handle the court cases and such within the state of Iowa. So, it was the Iowa Judicial Branch that called up Coalfire and asked the company to come and do a penetration test on the courthouses themselves.
JUSTIN: It was full-scope for a team penetration test. So, it included things l external pen testing, web application testing, 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 kinda do a real-life scenario. Like, can you gain access to our facilities? Can you plug in a — what we call a drone, a remote device, to be able to access that network later once we’re offsite, and then conduct the internal network penetration test from there? Throughout the whole time, we’re contacting with the guys at iowacourts.gov.
JACK: 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. 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, 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 8, and Friday, September 13. 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? Yes. Does Coalfire have permission to use lockpicks to get in? Yes. Does Coalfire have permission to plug USB drives into computers that they get access to? Yes. Does Coalfire have permission to disable alarms? No. 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.
JUSTIN: So, that gets filled out 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 JB building we discussed with the client Floors 3 and 4 are specifically off-limits during daytime hours because there was gonna 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 3 and 4. Then we enumerate with them; we’re like, okay, well, what if we’re in there after hours? What do you want to see from there? Is that open access? Like, yeah, that’d be more acceptable, but you know what? Let’s play it safe and just show us to see if you can breach the doors that enter on that floor. So, the contract will say something like, okay, JB building, Floors 3 and 4 are off-limits, and you see how big those fields are in that table. So, it’s really like the bare information that the project manager wants in there. Then we have a good understanding what the client — of what they’re actually looking for.
JACK: So, actually, this rules of engagement document I’m looking at is twenty-eight pages long, 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 words. It’s not fully documented in the scope of work or rules of engagement.
GARY: 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…
JUSTIN: This — we couldn’t work.
GARY: A hundred pages long. The amount of discussion that we have on what it is exactly they want us to do, it would be unfeasible as far as a rules of engagement would be concerned. So, again, that’s why we have the phone call. That’s exactly why we have, so we can say this is what we understand, what exactly do you guys want, and then we’re all on the same page when we show up.
JUSTIN: They’re like, we’re gonna 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 document, which would have been great if we did, but…
JACK: The Iowa Judicial Branch has actually worked with Coalfire 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. 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. These are three people who worked in Iowa’s Judicial Branch who contracted Coalfire to do these tests. 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.
JUSTIN: We touched down Sunday night. We entered in a facility. So, I don’t want to provide too many details that haven’t been already disclosed.
JACK: Alright, fine. Unfortunately we’re not gonna be able to go into every detail of what happened, because I don’t want to expose any actual vulnerabilities over there at the Iowa County Courthouses. But let me give you an idea of what they’re capable of. [Music] First of all, these guys mentioned 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. This is for doors that have a handle, that when you push down, it opens the 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. 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. It’s actually pretty simple. 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 lock-picking, it might take you a while, maybe ten minutes, maybe thirty minutes to get a lock open. So, it just takes more skill and time.
GARY: 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…
JUSTIN: A Von Duprin.
GARY: 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 doors, double doors that come together without the — what’s it called in the middle there?
JUSTIN: The mullion.
GARY: The mullion; is that what it is?
JUSTIN: Yeah. There’s another term for it, too. But there’s an — there’s a bar that runs in-between the doors where you’re not supposed to be able to insert tools.
GARY: Right. 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 and it opens the door. What we have come up with that we 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 cutting board. 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 door, you pull it down until that cutting board rests on top of the latch. Then you’ll apply pressure down on that latch and you start pulling the cutting board towards 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. If that latch doesn’t have the deadlatch latching it properly, you will open the door every time.
JUSTIN: So, typically when we’re talking about door bypasses, we’re inserting a tool through whatever method that we can, whether it’s in the inner-leaving 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 Von Duprin crash bar or the latching mechanism itself or some peripherals like a request-to-exit sensor.
GARY: But I can, what, 80%, if you had to put a number on it — 80% of doors can be bypassed by bypassing the latch.
JUSTIN: Right.
GARY: Just by manipulating the latch itself, you can get into 80% of facilities.
JACK: Just coincidentally, can you tell us where you guys are this — or what you guys are doing this week?
JUSTIN: This week we’re doing three two-day courses comprised of physical access control systems, alarm bypass techniques, and then safe manipulation. So, really kind of an action-packed week for us. That’s all the kinda juicy James Bond-style stuff.
JACK: 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 used to bypass the doors of these buildings, you can take a pretty good guess that they’ve got many options they can use to get into each door that they run into.
JUSTIN: So, pretty much we walked up, assessed the perimeter and kinda 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.
GARY: When we get into a place, it depends on — it also depends on who, 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 is a certain — you know, he’s your teammate, so you’re proud. You’re like, wow, dude, that was really fast. Like, that was really, really fast. Justin and I have been working together since he’s been here. 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, with a guy, and then when he’s on his fifteenth red team, and you’re like, dude, you’re getting really, really, really good at this.
JUSTIN: Yeah.
GARY: But you get to see that progression. So, there’s — 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 and years and years.
JUSTIN: I was gonna say, I’m tearing up over here, ‘cause Gary is honestly — like, I do need to take a moment to thank him. He taught me so much of what I know. Like, yeah, of course Deviant and some huge stars in the industry — you can learn so much by watching YouTube and learn how to assess the security of your facilities. But Gary was the first guy who handed me the under-the-door tool and taught me how to use this when I didn’t even know which end of the stick to be holding onto, which is a very common thing when people are given an under-the-door tool.
JACK: So, they get in, they look around for ways to plug in a drone and to take any photos of security problems 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.
JUSTIN: But we had gained access and we left a calling card. I just left a business card on one of the point-of-contact’s desk to the point where the next day he had e-mailed me and said, I guess I owe you a congratulations. We’re going back and forth over e-mail. I’m like, yeah, we found some really severe vulnerabilities that — 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. Then, yeah, Tuesday rolls around.
JACK: [Music] So, it’s Tuesday night 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.
GARY: We make it through the first door really easy, and then the second door — we could have used the same attack, but we were trying other things.
JUSTIN: Right.
GARY: And we weren’t having a lot of luck with the other things, but we didn’t really want to try the first attack ‘cause we wanted to see if we could use different techniques to get in, right? We found other areas that we can attack, so we went around a different area and we were working on — Justin was working on one door and I was working on another. I don’t know, did you ever get that door opened?
JUSTIN: I picked the lock.
GARY: Multiple…
JUSTIN: Yeah, like each way, and nah, something else was going on. There was a secondary latching mechanism there.
GARY: 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 cameras.
JACK: 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 and what’s going on in the whole building.
GARY: 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 sheriff’s desk during the day that sits there. So, they’ve got a sheriff that — or a deputy sheriff…
JUSTIN: Right.
GARY: That monitor or that’s there on duty for the courthouse that sits in this — it’s almost like a…
JUSTIN: Eh, a front desk, almost.
GARY: Yeah, like a front desk-type thing, where a receptionist would sit in a company. So, the deputy sheriff sits there, and it has access to all these different cameras. It would show the courtrooms or office areas. So, at night when you got your security guard there who isn’t a deputy sheriff, they will also use those same cameras that the deputy sheriff normally sits at to check the different offices to make sure that nobody’s in there, the lights aren’t on, and so forth.
JACK: So, one of the first things they 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, looking for security problems and being careful to stay very quiet. As the two of them wandered around this courthouse, they opened a door which tripped an alarm. [Alarm ringing] Suddenly the doors were buzzing and the alarms were sounding.
GARY: [Music] What had happened is they have — 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 for jail 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. Because of the — again, an assumption, because of the people that are [inaudible] there, they make sure that if that door is left open, that an 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 propped the doors open. Let’s close that; duh.
JACK: 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. But another successful mission for these two.
GARY: But that was fun.
JUSTIN: Oh, it was a great time.
GARY: Yeah. We were pooping and snooping and we were dodging the security guards, and he was looking at the cameras and we were hiding out and stuff. It was good stuff.
JACK: 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 Adel, Iowa. Let me describe the scene to you. [Music] The town of Adel is small. It has like, 5,000 people living there at most. It’s cute, though. It has a historic Main Street USA type of feel to it. In their downtown area the roads are covered in a red cobblestone brick, which gives it a more rustic feel, and all the buildings downtown look like they could all be historic buildings. The most prominent building in all of Adel is the Dallas County Courthouse, their target. 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.
GARY: Well, we stopped and got the Bomb Burrito at the gas station. That’s important.
JUSTIN: Yeah, that does come up later.
GARY: We did have a snack. [Laughing] [Crosstalk] We did have a snack. We took like a thirty-minute break and just hung out at the gas station talking to the clerk that was there. He was a nice guy.
JUSTIN: He was a nice guy. He gave us free donuts.
GARY: Yeah, he did give us free donuts. Instead of throwing them out, he just gave us some free donuts. Yeah, so we had our break, which was literally — I mean, the gas station was across the street from…
JUSTIN: Just about, yeah.
GARY: Yeah, like, almost across the street from the courthouse. We sat there for thirty minutes. We kind of scoped the place out just to make sure that they didn’t have some sort of patrol or something, city cops or deputy sheriffs that were patrolling the courthouse. So, we parked at the courthouse.
JUSTIN: Oh yeah.
GARY: And we — again, we’ve got a get-out-of-jail-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.
JUSTIN: Right.
GARY: We don’t have to be super sneaky. 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…
JUSTIN: Right. Don’t degrade our security. Like, don’t disable a sensor so that anybody could go up, bypass the store, and gain entry without an alarm going off. So, that’s a pretty common theme with a lot of our clients. 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 off alarms.
GARY: Right. So, in this instance we walked up to the north door, I think it was.
JUSTIN: [Music] So, we go up to this courthouse. We jiggled the door. There’s a little technique that you just see if the latch is engaged, and pop the door real quick. Much to my surprise, the door was open.
JACK: 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?
GARY: When he opened the door, the alarm did not go off. So, our assumption was there was a fault setting in this alarm system for 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. Then I tried a badge we had cloned from another building just to see if they had multi-building access. That didn’t work. It’s kind of like, well, should we give them the benefit of the doubt or should we just use this? So, we elected to basically close the front door and say, okay, well, let’s start over.
JACK: So, they both stepped back outside. This time, they closed the door all the way. It latches shut. This must have been a fluke 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 in through these doors, they have no trouble getting the door back open. [Alarm beeping] Now, as they get this door open, they immediately hear the alarm is beeping.
GARY: Right, just like in your home security system when 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.
JUSTIN: Yeah, and we already had an idea before that. We kind of expected that alarm to go off. So, just, again, a little bit of precursor to that. The other locations, nobody had showed up. Nobody responded, so we had 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 kinda coming up here, and we’ve been there throughout the day and we had seen the alarm panel. It said, OK, disabled. That night it said, OK, armed. So, we expected it to go off. We’re going — coming up to this facility hoping for once, this final facility, the alarm would go off at this location. So, it was almost like bittersweet but good. Okay, great, the alarm’s going. It’s beeping at least, once we go in there.
GARY: At least it’s armed.
JUSTIN: Right? So, eventually the alarm counts down and then it starts sounding. [Alarm ringing] So, very audible at this point. The entire downtown of Adel is going off and you can hear the sounders going off.
JACK: The sleepy town of Adel is now being woken by these alarms coming from their precious, historic, iconic courthouse building in the middle of town.
JUSTIN: [Music] So, at that point, alarms are blaring throughout downtown. We decide to go up to the third floor. So, we’re very well aware at that point. It’s very audible that the alarms have been activated. They’ve been tripped. At this point we go up to the third floor and get a vantage point and hoping that police presence responds to the incident, to the alarm going off, ‘cause it’s not uncommon. I’ve been in banks in the past literally a hundred feet from a police station where they either were not paying for the service or it wasn’t connected or configured properly, where it didn’t dial out and call police to respond to the incident. So, yeah, so it’s not terribly uncommon for that to happen. So, we go up to the third floor, get a vantage point, and at this point, for our reporting purposes, hoping that police respond to the alarms going off. At which point within — it was extremely quick 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? There are police. It’s a very – not a high-stress situation, 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 and Gary’s calling out commands. 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. We didn’t hear any doors opening or closing, so we start proceeding downstairs.
JACK: 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.
JUSTIN: The 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, what’s up, fellas? We’re like, hey man, we’re here testing the security. Do you want to talk? Can I open this door? Just keeping my hands static, not moving anything. He’s like, yep, go ahead, open the door. I’m like, okay, I’m gonna open up the door now. So, pushed the crash bar, we walk outside, and we greet him. At that point just start conversing with him; officer, we’re here, we were hired by Iowa State Courts. We’re assessing the 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 backpack pocket. Do you mind if I make a move and pull that out of my pocket? Sure, go ahead. Then at that point present our paperwork. So, from there, he asked for our IDs. At that point I think somebody else had shown up right at that point. So, they were escorting us, they had hunkered down with us while somebody else had taken the IDs and the paperwork away and started verifying our information.
GARY: At some point I think the sergeant even told us to relax, ‘cause we were trying to be ultra-careful and professional, and every time we wanted to move our hands, we were like, hey, is it alright? We okay to get our wallets? 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 guys can — you don’t have to be that paranoid. We are pretty sure that you’re not doing anything nefarious here. They were ultra-professional. They handled themselves perfectly.
JUSTIN: Yeah, those guys were great.
GARY: They were nice, they were professional, they were doing the whole 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 gonna make sure. We’re gonna verify that you are really supposed to be here. So, we can’t — if nothing else, we can’t thank the deputies enough because they were ultra-professional and just really, really stand-up…
JUSTIN: Agreed.
JACK: They immediately gave the police their get-out-of-jail-free card. You don’t want to mess around 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 of the state employees that hired Coalfire to do this penetration test. The police call the first number. No answer. They call the second number. The line was disconnected. They called the third number. Someone picks up. The police ask if they knew that these guys were trying to break in the courthouse. They said…
JUSTIN: Yeah, we’re doing security testing. Those guys are supposed to be there. They’re testing the security of the courthouse. This is my story of what happened, ‘cause I’m not on that call there with them. They had walk away a little bit from us.
GARY: 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.
JUSTIN: So, they run our credentials, everything on spec. We give them our names and our driver’s license. They do get ahold of our point of contacts. They’d say, yes, these guys are here testing security. So, at that point the sergeant, the guy in charge for — or head in charge…
GARY: The ranking officer on the scene.
JUSTIN: Ranking officer, thank you. That’s what I was trying to get to — had come back to us, handed us back our IDs, and he’s like, yeah, as far as I’m concerned, you guys should be good to go. Everything’s all clear here. So, at that point things get really jovial. We’re laughing, joking around with the officers. They’re asking us, man, this job’s crazy. Like, you guys break into buildings. Like, how does this go? How’d you get jobs like this? How can we test security? How do we get a job like that?
JACK: [Music] Just as Gary and Justin were about to leave, another squad car pulls up. This one has Sheriff written on the side. The guy gets out and walks up.
GARY: The sheriff shows up. He’s visibly upset. From our perspective, the mood completely changed. So, prior to him showing up, everybody was happy and smiling and we were – there had to be eight deputies that responded, all of us standing on the courthouse steps, and then there was one City of Adel officer there as well, so there was at least nine people there including us.
JUSTIN: There’s not a lot going on in Adel, Iowa at 2:00 in the morning.
GARY: Yeah. So, when the sheriff shows up, all the smoking and joking stops, right? This giant fun sponge walks in the room and everybody just stops talking. Just — everything just goes silent. He walks up. He has some choice words to say to us that we didn’t necessarily agree with, kinda talking down to us in a certain respect.
JUSTIN: To put it mildly.
GARY: 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 knew that. We told him our perspective which was, hey, we’re under contract, we’re working for these people. [Music] His response to that was, well, they don’t own this courthouse and I don’t care if you’re under contract. They don’t own this courthouse.
JACK: Whoa, what? The state doesn’t own the courthouse? 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.
GARY: Nah, 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. Not frequently, but it happens. So, if that happened in this case, we were fine with it, ‘cause we know that the truth’s gonna come out, they’re gonna realize that we’re actually working for a company and that we were really contracted by the state. So, worst case scenario, we gotta spend an hour or two in a holding cell. Not that big a deal. [Music] The sheriff tells everybody that was there; says, well, we’re gonna arrest these guys for trespassing. Hold them. I’m gonna go make a phone call. So, in our minds he’s gonna go talk to our contacts. At least in my mind that’s what he was doing. In that time that he was gone — ‘cause he was gone for like, a good ten minutes, it felt like.
JUSTIN: Yeah, it seemed like he was, for sure.
GARY: In that time he was gone, the mood went right back to what it was before he was there, which was everybody was asking us questions, asking us how we did stuff. What’s the craziest thing we’ve ever seen or heard about in our line of work? Like, it went right back to that. One of the officers was super interested on how we got in, so we showed him our tools, we showed him how we got in, we showed him the technique that we used. 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. It was — everything was — just went back to normal. About ten minutes later, again, what we’re thinking, he came back in and he was just like, you need to arrest these guys for burglary. All the sheriff’s deputies kind of looked at each other. 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. I don’t know what Justin’s – who the sheriff or the deputy sheriff was that arrested Justin, but the guy that grabbed me, he puts his hand on my shoulder and says, hey man, I’m really sorry about this. You’re gonna…
JUSTIN: I think something very similar happened with me, as well.
GARY: Yeah, he goes, you turn around. I’m gonna have to put these cuffs on you.
JUSTIN: Right, and I totally understand. Like, okay, man. I get it. I see where you’re coming from.
GARY: Yeah, and both our responses are like, hey man, it’s okay. You’re just doing your jobs. It’s not a big deal. This won’t be the last time this happens, I’m sure.
JACK: So, both of them get handcuffed. 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.
GARY: No.
JUSTIN: ‘Cause think about it from our perspective; 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 Adel, Iowa to start breaking into courthouses on our [inaudible] paths. We knew we had every shred of evidence in our favor. We knew that this was totally above ground. It’s not totally uncommon for law enforcement to respond to an incident. It does happen. It is extremely rare, I’d say, for somebody to get detained or furthermore arrested. That’s as far as it had ever gone, and as far as we’re aware, nobody’s ever been actually formally arrested and pressed with charges.
GARY: Yeah, charged, nobody’s ever been actually charged, yeah.
JUSTIN: Right. So, we’re thinking, okay, we’re gonna go down to the station. We’ll work this out, not a big deal.
JACK: Now, because this is Adel, 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, ‘cause when we come back from the break, we’ll hear what happens to Gary and Justin. Gary and Justin are now both at the jailhouse, and they have been separated. The police are questioning them and processing them separately.
GARY: That’s when the aggravation started to kick in a little bit, [music] 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.
JUSTIN: No, I never talked to the sheriff.
GARY: Yeah, yeah. So, I interacted with the sheriff a couple of times, and it was like, hey sheriff, are you just gonna hold us or are you actually gonna charge us? It was later discussed or during that conversation that I won’t really go into ‘cause 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 of it…
JUSTIN: De-escalate.
GARY: Right. Yeah, that’s a better term, de-escalate the situation. Like, hey, maybe you could contact one of our contacts. Talk to somebody at Iowa State Court and talk to somebody, because we’re legitimately just working here, sir. We were ultra-polite. There’s multiple videos out there that show that I don’t think we were ever unprofessional. We were just like, hey sir, could you possibly do this or check with this person? Or, maybe this is a big misunderstanding. It was always met with nope, you’re going to jail. Nope, you’re getting arrested.
JUSTIN: I mean, at some point along that process it became very clear that regardless of any amount of paperwork that we would have had on us…
GARY: It did not matter.
JUSTIN: …or anything that we could have said, there was something else going on. It wasn’t about that. We had the paperwork. The deputies already verified, cleared, identified us but let us go, essentially. So, despite all that, 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 that point. We’re both being very professional throughout the entire process. But I’m a very big privacy advocate, and as we’re going through this, they’re asking what’s your marital status? What’s your highest level of education? I’m very — understand at this point we’re being wrongfully arrested because we’re here for a job. This isn’t something that needs to be dragged through a criminal process. At most, if there’s contract discrepancies or 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 number. So, it’s not like we’re resisting 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 booking or reception room, however you want to call it, got very upset with that. So, we have to give up all of our tools, all of our gear. We go through the process of explaining what these tools are, ‘cause we’re being booked not only for burglary but possession of burglary tools. So, they want to have circumstantial evidence of us having tools that are used typically in burglary trade but obviously in a security setting at this point.
JACK: They finally get to make some phone calls, but at this point it’s like, 2:00 a.m.
GARY: I had about thirty. But unfortunately everybody was sleeping and no one would answer my call. Like, even my wife slept through all of the phone calls that I sent. I sent all sorts of messages to people. The only person I was able to actually get ahold of was one of our contacts. I said, hey, are you aware that we got arrested? Yeah, yeah, we’re aware. Such-and-such told me. Are you doing anything to get us out? He said, well, yeah, we’re gonna be there first thing in the morning. We’re gonna talk to X, Y, and Z. I don’t remember who he said we’re gonna talk to. We’re gonna smooth this all over. It’s one big misunderstanding. You’d think — I believe almost verbatim his thing was, you’d think that the sheriff would be a little more understanding of what we’re trying to do. I said, well, guess what? He’s not. He said, yeah, I can see that. Again, we’ll be there first thing in the morning. We’re gonna hammer this out. There was a lot more to that conversation, but that’s the gist of it.
JACK: Now, for me, my first call would have been to my boss. I would have called Coalfire 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 Coalfire, so Coalfire should be capable of helping them out.
GARY: Yeah, and we tried to get ahold of Coalfire. We just couldn’t get ahold of anybody just because of the late hour. I think most people when they sleep, they put their car — they put their phone on vibrate. Because again, we’re talking about a scenario that has never happened before. So, maybe you want to say some complacency, whatever you want to put in there. Who knows what it was? But most people were like, okay, 2:00 or 3:00 in the morning, not really that big of a deal. What’s the worst that could happen? Well, we figured out what the worst that could happen was.
JACK: By 2:30 a.m. the police finished processing them and gave them both orange jumpsuits to change into, the kind you see prisoners wear. 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 with other criminals and cell mates. [Music] They tried to lay down and sleep, but the beds were really hard 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.
GARY: When we were — when we walked over there in the morning, although it was incredibly uncomfortable and embarrassing that we were over there in literally shackles, right, the whole around-your-wrists and then tied around your waist and then the chain that goes from your wrist or your waist all the way to your ankles, and then you’re attached to the guy in front of you, and you do the – what is it? The railroad gang or whatever across the street with deputies in front of you, in the back of you. I was like, you gotta be kidding. We get over there, and the whole time I’m thinking we just gotta make it to 9:00 in the morning. The state’s gonna be here, they’re gonna explain everything, and then the judge is gonna be like, this is silly. Why are you guys here? Go ahead, issue on your own recognizance. You can go home.
JACK: So, they get to the courthouse, they sit down in the courtroom, and await their names to be called by the judge. 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.
GARY: I was first.
JUSTIN: Yes.
GARY: There was a gentleman that was sitting next to the sheriff. The sheriff was in the gallery, I guess you could say. There was only one man standing next to him. So, my thought was, good, that is the court representative from the state court, right? He’s talking to the sheriff, they’ve talked about this, they realize this is just a big misunderstanding. Everything’s gonna be good, they’re gonna let us go, is what’s still playing in my mind. I sit there, I go in front of the judge. They ask your name. They say, what’s your name? Yeah, my name’s Gary DeMercurio. How much money do you make? I make X amount of money. Who do you work for? I work for a company called Coalfire. So, at that point they decide whether or not you can qualify for a public defender.
JUSTIN: Legal representation.
GARY: Right, public defender. She says, you do not qualify for a public defender. Would you like to defend yourself or would you rather get outside counsel? I’m like, well, I’m hoping outside counsel isn’t necessary because, ma’am, I believe this is just a big misunderstanding. So, I launch into my reason why I think this is a misunderstanding. I explain to her what it is that we do, what we were doing that night, who we work for. She looks at me and she says, you must think I’m stupid. [Music] At that point I’m like, oh, Lord. You’ve got to be kidding me. This is not happening. She launches into this, I don’t know, diatribe, 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 employee, 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, etc, etc, etc. I just went from being hopeful to just seeing red. I was just irate.
JACK: Keep in mind that both Gary and Justin barely slept the night before, and they’re in these orange jumpsuits with shackles on. They aren’t presenting themselves as best they could given the situation, 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…
GARY: You are a judge. You are — literally the point of your position is to be able to look at someone 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.
JUSTIN: Which obviously he’s not saying that to the judge, but that’s going through both of our…
GARY: Yeah, that’s obviously what we’re thinking.
JACK: 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.
JUSTIN: Same deal. I’m like — as not the person on front stage but obviously still in the same boat, I’m like, oh no, there’s no way. This is like a bad joke. You gotta 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. My jaw has dropped to the floor looking at the situation transpire in front of us.
GARY: There’s still this gentleman sitting next to the sheriff. I’m like, okay. I’m like, well, again, internal monologue, well, hah, joke’s on you judge, this guy’s from the state and he’s gonna explain everything. So, this guy walks up next to 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. I’m like, oh Lord. 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. They told us they were gonna show up. They ghosted us, 100% ghosted us.
JACK: 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. This was just too soon for anyone from Coalfire to be able to come down and help, either. So, they were just standing there completely baffled and irate that this was happening.
JUSTIN: 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…
GARY: He just smiled and shrugged. He didn’t say anything. Again, in 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 nature.
JUSTIN: Sure, yeah, anything.
GARY: Not a word.
JUSTIN: Nothing.
JACK: What a frustrating situation. Yes, they broke into 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.
GARY: Then she read the address of where we broke in. She realized that it was her courthouse and her courtroom, and she was mad.
JUSTIN: Irate.
GARY: She was like, how dare you break into my courthouse and my courtroom at this address? She just went off. Then she’s like, bail is set for $50,000. Our bail originally was $5,000.
JUSTIN: Ten, ten times [inaudible] bail for burglary.
GARY: Yeah, ten times the amount.
JUSTIN: Yeah.
JACK: That’s just how much bail was set for Gary.
JUSTIN: So, I go up shortly there — 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 to perform this testing. After seeing what Gary had gone through, I’m like, there’s no point. Don’t open your mouth and say something that could be potentially incriminating here. So, I’m like, okay, we’re gonna do this, I suppose. Gary and I again trudged back across the street, back into our holding cells where Gary has cell mates 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 disrespected you. Even the inmates just looked at us. They were like, man, you guys are so innocent. They didn’t even have to listen to our story. They were 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?
JACK: Justin’s bail was also set for $50,000. So, the way bail works in the US 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.
JUSTIN: At that point we’re facing felony charges. We’re facing felony burglary charges and felony possession of burglary tools. So, we’re in a criminal trial at that point, so…
GARY: And looking at seven years in prison as well, seven.
JUSTIN: Right, right.
JACK: Still, they hoped any moment their point of contacts would come and sort everything out. But the situation was becoming less hopeful, so Gary and Justin got some more phone calls and eventually got Coalfire on the phone and tell them everything, and Coalfire immediately started working to bail them out and to get help. So, about twenty hours after going to jail, the $100,000 in bail money came through and they were let go. At this point it’s Thursday and their return flight is on Saturday.
JUSTIN: Oh yeah, Coalfire gave us permission. They’re like, do whatever it takes. Get out of that state. Come back home, boys.
GARY: Leave that place.
JUSTIN: Yeah, we booked earlier flights.
JACK: [Music] Both Gary and Justin go back home and get lawyers to help them with this. 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.
REPORTER: Two men arrested for breaking into the Dallas County Courthouse say they were hired to do it by the state. Justin Wynn and Gary DeMercurio are both now charged with third-degree burglary and possession of burglary tools. They were taken into custody around 12:30 Wednesday morning. As KCCI’s Alex Schuman shows us now, the men say they were doing cybersecurity work.
ALEX: 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.
BYSTANDER: They need to be arrested. There’s no trying to break in, period. Lock ‘em up. Throw away the key. I don’t care.
JACK: Well, that bystander 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 gonna happen, but then Coalfire 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. But then Coalfire said, we left a calling card on your desk overnight and you e-mailed 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 were 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 ran out of fingers for pointing at Coalfire 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 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 authorization 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, 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 into the building. So, from the prosecutor’s perspective, they thought these two guys were actual criminals.
GARY: Well, so, here’s the caveat, is after all this was said 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. The final findings, which are public — the very end of those findings, that lawyer is looking at some sort of precedence, right? All law is based on a case before, right? That’s where you get your legal precedence. Well, what was — in a similar scenario, what was the judgment? 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.
JUSTIN: Yeah. It’s their authority to protect that courthouse and administer security for it.
GARY: Right, and the things within that courthouse.
JUSTIN: Right.
JACK: But the prosecutors held their position. They started looking through the contract to try to find anything that wasn’t right. Justin and Gary both went back to work for Coalfire 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. This is hard to find time to do when you’re typically spending a week at a client’s site doing a penetration test. This news made its way around, so if Gary or Justin got on a call with a client to do a pen test, some clients wanted to hear the whole story about what happened in Iowa. So, it was just really distracting. Of course, they were arrested with felony charges, so 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. 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 Ars Technica, which got a lot of the documents and posted them publicly. Here is where I see the rules of engagements and the positions that the state took on various things and how they broke into 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 outside 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. 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 Coalfire to run these tests and the state point-of-contacts all approved that Coalfire was hired to do it, all this came together and was given to the county prosecutor.
JUSTIN: 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 pressing charges, at which point they decided, okay, felony charges aren’t really relevant here, but we’re gonna 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, we’re legally hired for this job. No chance in hell we’re gonna 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. That fight took place over the next four months.
GARY: All sorts of fights between our lawyer and the prosecutor.
JUSTIN: Oh, constantly.
GARY: To even get to the point where the prosecutor’s like, okay, well, maybe we’ll drop it down to criminal trespassing. 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. 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 to – I mean, they were grasping at straws to do anything and everything in their power 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, these Class C felony charges with seven years of prison time behind it for I don’t even – I still to this day have no idea why they kept pushing so hard for this stuff.
JACK: 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 were given felony charges.
JUSTIN: So, that’s kind of why we’re still so upset at this point. We’re gonna carry this for the rest of our lives. We have felony arrest records. Even though charges are dismissed, 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, and any number of things; volunteer work, it’s gonna show we’ve been arrested on felony charges. So, we’ve been stripped of rights with no due process on wrongful arrest.
JACK: Yeah, it’s a shame. Any traffic stops these guys get — when the police look up their record, it’s gonna show that they were once arrested with felony charges. 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, they have real charges. Any background checks that someone does on these two is gonna show their criminal history. I mean, what do you write when you’re applying for a job and it asks you, have you ever been arrested? What do you put? Yes, but it was wrongful? It doesn’t sound fair to me.
GARY: Big things, little things. It just affected our lives for the last six months, like all the time.
JUSTIN: And honestly still will continue to do. Like yeah, with the arrest charges. But man, just honestly, I know a lot of people say a lot stuff; oh, damages, I’m so stressed out over this, and they want to do a counter-lawsuit. Like, no, I think my physical brain chemistry has changed over this, being so stressed out. I sound like a wimp about it, but man, you wouldn’t believe it until you’re in it and going through something like this how stressful and traumatic — I don’t even want to use that term ‘cause I don’t think — but it is 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 in the right, and then to see the legal system fail you repeatedly. There were so many opportunities and avenues for the county to understand or get more information and then drop the charges, and it just never happened.
GARY: 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. It was just – it was — for the lack of a better term, it was like I was flabbergasted, like totally old school, right? It’s just, 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. Why are you still pushing seven years of prison time? Why are you still pushing this on us? It’s like, they had absolutely no mindset, for lack of a better term or maybe it is the best term, destroying two professionals who have absolutely sparkling clean records who’ve never even been in trouble for jaywalking before. They’re just like, oh, no, yeah, no big deal. We’ll just keep throwing these Class C felony charges at them. Yeah, you know, if we drop it later, whatever. It doesn’t affect us. It doesn’t harm us. What do we care? Just like, the – what do I want to say? The lack of sympathy or empathy…
JUSTIN: Professionalism, empathy.
GARY: Professional, whatever term you want to throw there, just for – not even us, but just another human being…
JUSTIN: For doing what’s right. If you’re representing the law, it’s a failure of the legal system, which I had no idea America worked that way. It’s just not the America that I was brought up in. I thought innocent until proven guilty, and just to see us stripped of so many rights and to go through this, it was just such an awful experience to be thrown into this mix.
GARY: Oh, it was terrible. 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.
JACK: And that is where we left off back in 2020, when this episode first aired. 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. [Music] They were outraged from this. This jeopardizes a whole industry. People who have gone to college to get degrees in this are now seeing like, wait, so 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. 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. [To John] After that news hit, what did you do?
JOHN: Oh, we immediately went to the town of Adel, Iowa, and we did Awareness Con. We invited the entire community to come down and ask the security community questions about what we do.
JACK: [To audience] Yeah, and because John Strand is the founder of Black Hills Infosec, 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. You heard that one 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 gonna 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 this.
JOHN: It’s absolutely wonderful. The sheriff, Leonard, he came and he talked.
JACK: Here’s that clip from Awareness Con, where the sheriff came to give his opinion of this whole thing.
JOHN: I’m very, very, happy Sheriff Leonard has shown up, and I asked him how he wanted me to introduce him to the group. I’m not joking; he said, you can introduce me as the bad guy. [Audience laughter] So, he has a great sense of humor. So, everybody, could you please give a round of applause for Sheriff Leonard? [Applause]
SHERIFF LEONARD: Well, first off, I’m sorry. I’m obviously the reason you’re all here, so — 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. That’s not — there’s just a whole lot of things that went into this that night that were still in question. So, you know, like I was talking earlier; getting a lot of hate mail and a lot of stuff from the industry worldwide, I mean London, everywhere, just getting ‘how dare I do this’. You know, you gotta 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 — and I had five deputies running 140 miles an hour to get there — that doesn’t work well, because if one of your family members was t-boned 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 gotta look at. The only reason — and the other thing; those of you that do the job, I would never charge you with a crime and let it continue — I don’t have the ability to dismiss it, but I can work with the county attorney and those type of things. But at the end of the day, if we believe that it truly needs to go away, it’ll 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. I rely on you folks to help us. The two gentlemen that night, they’re good guys, but you gotta understand that when you come here in rural Iowa from Florida, you’re from Seattle, Washington, chances of you coming back when I ask you to come back and answer questions are slim to none, I promise you that. So, we just — I just met you, so you’re not gonna — there’s a whole lot of questions that go into these things in the middle of the night that we have to — 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 kinda wait for it. We’re not out to prosecute anybody. I would never charge any one of you with a crime if I didn’t think it was valid. 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. 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 would have helped you do it. You know, I would have helped them accomplish their mission that night, so — and we wouldn’t have any of these problems. So — but anyway.
JACK: I think Awareness Con 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. They were starting to come around and feel sorry for them. Some were even saying, please don’t judge Iowa based on this. So, while I was at DEFCON, I ran into those two penetration testers from this Iowa County Courthouse 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. [To guests] So, you got arrested, got your charges, got the charges dropped. Story’s over, right? Anything else happen since then?
GABBY: A couple things.
JACK: What’s new with you?
GABBY: I mean, so, have you ever heard that thing where like — you go to prison and you turn gay? Yeah, I’m not gay, but definitely turned into a girl.
JACK: Gary has changed her name to Gabby.
GABBY: Well, it’s my handle. I just, I guess, absorbed the handle Gabby, yeah, ‘cause I can — like to be anyone I want to be.
JACK: 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.
GABBY: I don’t feel like it was like that at all because there was so many things they said that just were not accurate or just outward lies, fabrications like changing the narrative just to say, oh, cool, we’re innocent. Well, no shit. Obviously we’re innocent the entire time, which is why we never settled for anything the entire time. So, them dropping it would almost be like them doing us a favor, which was not the case. They did themselves no favors by dropping it other than embarrassing themselves further. That was for them, definitely not for us.
JACK: Well, what more can you do after charges are dropped?
GABBY: 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 dragged through the mud, they lie about everything, and then there’s zero repercussions unless you go after them for a personal suit.
JACK: [Music] 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.
JUSTIN: I think Gabby was already thinking about you looking at her mugshot, smiling in there. She was already thinking about the lawsuit as soon as the cuffs went on.
GABBY: Pretty much.
JACK: You were in the jail cells saying, as soon as I get outta here I’m gonna sue these guys.
GABBY: Oh, my — ‘cause I knew we had done — 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.
JUSTIN: Oh, I don’t trust them to give me my information. I saw how they secure things.
GABBY: But that was — it’s a good learning point, right? Because we’re like, we did nothing wrong. We’re gonna be completely cooperative. We’re gonna do everything, and then you do everything right, and then they just lie about stuff to try to cover their own butt and to try to make it look like they didn’t do anything wrong. You’re like, wait a minute, 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. So, not cooperating to me sounds like the right choice after going through that.
JACK: 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.
GABBY: We actually had our original lawyer and we asked him. Like, I think we would really like to go after the county and the state and the sheriff, because people need to know that this is not okay. Like, they just can’t get away with stuff like this. He had a real — he was afraid to do it, for lack of a better term, because he’s like, this is small-town Iowa. It’s not big. Everybody knows who I am, and I feel like if I go after the county and the state and 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.
JACK: So, their lawyer made a few phone calls and found them another lawyer named Marty who was just about to retire.
GABBY: He’s a civil rights lawyer and he loved the case. He’s like, I will take it on. I’ll do it pro bono. He’s like, I’ve made my money. Like, I — he’s literally at the twilight of his career. He extended his career to finish this case.
JACK: So, they got a new lawyer, and they wanted to sue the sheriff, the prosecutor, the judge, all these people who treated them bad. But this is where Gabby and Justin started learning some new words, words like…
GABBY: Qualified immunity.
JACK: 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. Then there’s sovereign immunity, which means you can’t sue the government unless the government agrees to be sued.
GABBY: 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 gonna sue you. Are you guilty? You’re like, of course I’m not. They’re like, oh, sorry, can’t sue you now because you said I’m — I said I’m not guilty. So, the state immediately threw it out.
JACK: 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, but then when they looked at it, they just kicked it back down to the state, who just closed it right away.
GABBY: So, it’s just like, they tried so hard to stack the deck against us at the — 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 they could take to stack the deck in their favor, they absolutely tried to do and absolutely did.
JACK: So, this lawsuit they wanted to wage was dead in the water before it even got a chance to begin, which is really frustrating because what mechanism can you even use here to bring justice to a situation like this?
GABBY: So, we were left with the county and the sheriff. 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. So, we had to go through the process of saying, these are all the things that we think he did wrong, and then the judge said, yes, yes, no, no, no. Then we eventually are 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. So, we had to go after the actual sheriff, which means he’s also covered by the county’s insurance policy, and nothing, not one cent comes out of his pocket. He doesn’t get reprimand — like, nothing, absolutely nothing happens to him. It’s a moral victory at best.
JACK: Okay, so they started a single lawsuit that got accepted in the courts against 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. [To guests] Now, my question is, what were you hoping to get out of the lawsuit?
GABBY: One dollar.
JACK: One dollar?
GABBY: That was all I cared about. I told… 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, that’s all I care about, which is — the entire time, which is why we were like — they were like, you should just take the trespassing charge, and — nope, nope, nope, the entire time. My entire goal was just to show that this — show this person for who he really was, which is just a lying, corrupt individual.
JACK: 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, and Gabby’s just coming out with claws out. This is gonna be a good fight. 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.
JUSTIN: We submitted the maximum amount that the insurance company would have covered for the county. So, we didn’t want taxpayers having to front more money for having a poorly-elected sheriff. So, yeah, that’s the dollar amount that we set. 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 isn’t okay. You can’t put hackers in jail and try to prosecute them when you hired them to help defend you.
JACK: 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. My guess is that they wanted to split $1 million. 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. 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 $1 million, I think that sounds reasonable for the amount of hardship they endured. But Gabby was still furious from this whole ordeal.
GABBY: Like World War II, the — what’s the saying? They woke the sleeping giant. Japan thought if they came in and they smashed us that we would back off and just slink away and not do anything. Kinda the same thing here where, oh, if we just throw our 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. We don’t fuck up. Justin and I, we do things by the letter, by the contract. Everything we do is meticulously perfect for that reason, because of what we do. We don’t want to mess up. 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, and they were unable to. 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. [Music] 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.
JACK: 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. 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, and the government just doesn’t care. 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 testers. This is an epic story. This case could set a precedent.
JUSTIN: It was just the right thing to do, I think. We didn’t have a choice, I mean, to have our counter-sue back at them. It was the only way to try to restore any sliver of justice around our case and that state. So, in our minds, it didn’t even cross it. Just a no-brainer; had to sue back. But the funny — like David and Goliath, I think that’s hackers, right? It’s like the power that one individual can hold is why governments can be so scared of these individuals. You can do a lot even as a single person. So, against the government, it is a mighty entity, but still, again, that’s kinda for our lawyer to handle.
GABBY: It’s all about the information, and we have all of it.
JACK: 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, to put the government in check when it overreaches and force it back. So, how does the county react to this? Of course they delay it. Their original court date was supposed to be in 2020, but that got delayed, cancelled, 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.
GABBY: The further they could get away from the moment, the better for them, because they wanted it to fall out. They didn’t want people to bring it back up.
JACK: 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 patience. 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 lawsuit’s gonna have, it’s not gonna 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, too, Justin and Gabby’s relationship with Coalfire started to sour. They didn’t feel like they were getting paid enough or treated right by them.
GABBY: The first year after we got arrested, we had over $5 million come in directly of people saying, hey, we want to work with Gary and Justin, and we want to work with the Iowa team, and blah, blah, blah.
JUSTIN: I think.
GABBY: We don’t care.
JUSTIN: Our story was one of the most valuable things that happened to Coalfire. Even the CEO recognized, yeah, the number-one reason Coalfire is known is because of this case. It is funny; if we ever talk to anybody and we mention, oh, we work at Coalfire — like, oh man, you ever hear that crazy story of those guys that got arrested? I’m like, no, tell me about that.
JACK: Gabby quit her job at Coalfire and went to apply at other places. [To guests] I didn’t quite get the full picture. Is Coalfire good or bad?
GABBY: Individuals at Coalfire are very bad. I think Coalfire as an entity during that time was good.
JACK: She was able to quickly get interviews at other places, but even though she was the best for her job and the most qualified, 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.
GABBY: Like, really started to come into question; like, damn, am I even gonna be able to keep doing this because of what happened?
JUSTIN: Great opportunity to start your own business, then, and do it on your own terms.
GABBY: Right? Yeah.
JUSTIN: Yeah.
GABBY: 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…
JACK: Starting something new yourself.
GABBY: 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.
JACK: Thus, Kaiju Security was born, a fresh, new penetration-testing company based near Seattle, Washington.
GABBY: Adversarial simulation offensive security.
JACK: Gabby started it with another guy named Marcus, and Justin moved on to the team shortly after it was formed. After getting this new company started up, the lawsuit was finally making some movement in year five.
JUSTIN: Yeah, recently in 2025 it was about showtime. So, then we started getting hot and heavy with it, doing depositions, getting things on record, getting prep for the trial case. So, we were definitely shaping up — yeah, go show up in court. Again, going back to the hacker community, we had some great people like Deviant, Andrew Porter, that agreed to testify in our case just as expert witnesses. So, yeah, we’re going through. We really thought we were gonna 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. They were throwing out low-ball numbers. I think they had like — just about like our bond or bail is what they first wanted to offer, like $50k.
GABBY: Yeah, $50,000.
JACK: 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. $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.
GABBY: 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. They were like, oh, we’ll give them fifty. Then so, the judge, TLDR — the judge comes by to us, and through the entire process — it 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 gonna get. So, I’m gonna go back and I’m gonna beat these guys up pretty good, and he leaves. Marty looks at us and is like, I’ve been doing this for fifty years or something like that, or forty-two years, and he’s like, I have 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, ‘cause 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.
JACK: 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 bodycam footage, get testimonies and depositions and bring in expert witnesses. They even took time off work to go attend this trial, and they booked their flights and their tickets, and they were ready to go. 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 zero-dollar settlement, or the government wins at trial. For them to receive more than $50,000 from this lawsuit is 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. 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 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. [Music] But then a few days before the trial was due to begin, in February 2026, they got a 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. The lawsuit was closed. They got paid. They won. This allowed them to celebrate.
JUSTIN: Still, I think the biggest one for the community is now we have better precedent, right? So, before, we were just arrested. Felony 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. 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 the county could have to pay out or — yeah. So, really good to have the win under our belt for the community.
GABBY: Everybody else, yeah. I’m obviously much more selfish than Justin is.
JACK: Now, finally they can go back to their normal lives feeling like justice has been restored in the best way it possibly can be. Now they’re focusing on building Kaiju Security all with a new feather in their cap.
JUSTIN: I love saying that, too, ‘cause I fought the law and the law won. No, man, the law fought us and we won.
JACK: [Outro music] A big thank-you to Justin Wynn and Gabby DeMercurio for reaching out and finding the time to share this story with us. 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 Low. 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 gonna have to wait for the public release, which is coming later this month. This show is created by me, pony pie, Jack Rhysider, 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 mark as read or mark as read? This is Darknet Diaries.