Pressure Zone a podcast by Hack The Box
Pressure Zone is a game-driven cybersecurity podcast where CISOs and executives are placed inside escalating, realistic risk scenarios that mirror the complexity of today's cyber leadership. Each rung requires the guest to make a decision under pressure, explain the rationale, and translate the impact into business terms, just as they would with a board, CEO, or executive team. The episode unfolds as a structured game, creating an engaging format that reveals authentic leadership judgment, tradeoffs, and security insight without feeling like a traditional interview or sales pitch.
Each episode is built around escalating rounds: connected, sequential scenarios that move from early warning signs to high-stakes incidents, where every decision shapes the context and pressure of what comes next. Guests must assess the risk, make a clear call, and defend it in business terms. If they dodge a question or avoid a decision, they trigger a Confession Card penalty, prompting an honest, insight-revealing response such as a hard lesson learned or an unpopular opinion. This keeps the tension high while preserving the realism, pace, and authenticity of the game.
Pressure Zone a podcast by Hack The Box
The Zero-Day Squeeze
Use Left/Right to seek, Home/End to jump to start or end. Hold shift to jump forward or backward.
An unauthenticated Remote Code Execution (RCE) vulnerability hits a deep open-source dependency inside your production microservices. The solo maintainer drops a proof-of-concept exploit and refuses to release a patch until corporate users pool a $600,000 sustainability fund.
In the fourth episode of Pressure Zone, host Christine Bartlett puts Chief Strategy Officer Caroline Wong into the executive hot seat. What begins as an ethical open-source strike quickly spirals into a high-pressure crisis involving SEC disclosure dilemmas, boardroom pressure to alter risk dashboards, an internal developer mutiny, and active internet scanning.
Faced with brutal trade-offs, Caroline must choose whether to risk database corruption with an experimental memory patch, pull rank on exhausted engineers, or aggressively amputate application features to save core database records.
Welcome to the Pressure Zone, a podcast where we push the world's top security leaders past their comfort zone. Today we are stepping into the ultimate supply chain deadlock, and we are joined by Caroline Wong, Chief Strategy Officer. Welcome. Thank you. Okay, let's dive in. Your global enterprise platform relies heavily on logback extension, an open source utility buried thousands of levels deep within your production cloud microservices. Three hours ago, the solo open source maintainer, deeply burnt out and frustrated by tech giants profiting off of his unpaid labor, posted a stunning announcement on GitHub. He has discovered a critical, unauthenticated remote code execution RCE vulnerability affecting all current versions of the library. He has not released a patch, nor has he logged a CVE. Instead, he dropped a proof of concept showing it works and stated he will withhold the fix until major corporate users collectively pull a 600,000 sustainability fund. The exploit is out there in the wild, no patches exist, your automated pipelines have nothing to pull, and malicious actors are already actively scanning the internet trying to reverse engineer his proof of concept. Okay, Caroline, you've spent your career teaching us what gets measured gets managed. You've built mature app sec programs founded on Software Bill of Materials, S-BOMS, aka the ingredient list, scalable gates, and continuous improvement. But right now, the open source foundation your entire software supply chain rests upon is facing an ethical strike. There is a live remote code execution in your stack. The maintainer is striking and the scanning traffic is flashing red. Let's see if your metrics can save you when the open source world decides to collect its debt. Are you ready to step into the zone?
SPEAKER_01I'm ready. Let's do this.
SPEAKER_00Alright. Okay, round one, the visibility chaos. It's 11 p.m. on a Friday. The maintainer's manifesto drops. Your automated software composition analysis, STA, dashboards are lagging, throwing timeout errors due to the massive nested dependency trees across your 4200 active microservices. Your instant commander asks for an immediate blast radius map. What is your leadership command? Okay, you get four choices. A the Delta Inventory, order a code freeze, and instruct your AppSec team to manually query the latest static SBOM artifacts in your artifact repository to map dependencies, accepting that offline data might miss shadow deployments. B the runtime trace deploy an emergency runtime profiling agent or EBPF probe directly into production clusters to observe live class loading and cache catch logback extension actively running in memory. C the blanket web application firewalls or WAF shield. Leave the application discovery running in the background and immediately deploy a broad signature-based rule across your edge or WAF to drop incoming string patterns matching the proof of concept. Lastly, D the technical evacuation. Instantly invoke service mesh controls to isolate your highest risk internet-facing application segments into a strict zero trust sandbox, breaking peripheral business workflows, but cutting off external input vectors.
SPEAKER_01When I'm looking at these different uh scenarios, um then I am interested in uh understanding what the latest SBOM says. I am interested in the Delta Um because ultimately I really need to know if this extension, if we're even using it. I need to know if we're affected. Um and so um that's why A is one of my possibilities. Um I also really like B. Um, A has problems, right? Because whatever the S bomb shows is a point in time. Uh, some time has gone on since then. Um so it could be out of date. And I don't know if it's five minutes out of date or if it's five months out of date. So that's kind of the um, you know, issue, if you will, with A. Now, B I like a lot because it says what's running right now. However, whatever is running at this particular point in time may or may not be the same as what's gonna run in five minutes or in five days. Um, and so both A and B, in my opinion, are a little bit constrained because they're each a point in time. I don't know if I'm allowed to do like multiple choices, but right now I like A, I like B. Um, you know, a signature-based WAF with which is which is C, the web application firewall, I wonder like, where's this signature coming from? Um, like, is it is it legit? Like, if if if a few assumptions are correct, which is that we can actually identify an active attack based on a signature. Like, if that actually works, yeah, I like C, and that's you know, defense in depth. Um, I don't love D. I don't love D because D has the potential to uh compromise availability. Um, and I'm not sure what kind of organization this is, um, but certainly there are organizations where like one second of downtime is real bad and we cannot stand for it. Um, there are others where it's okay. Um, so at a high level, um, you know, I don't know if I'm allowed to do this, but I would say like A, B, and C, not D. Any of the various options is not gonna give us a comprehensive or a perfect answer. Um and so I think kind of in reality, I would send folks after A, B, or C. Um. I'll pause to see what you think about that.
SPEAKER_00I'll I mean, I'll let that slide, but then the next one you definitely have to pick one.
SPEAKER_01All right, let's do this. Cool, let's go.
SPEAKER_00Okay, round two, uh, the materiality threshold, the SEC dilemma. It is 9 a.m. on Saturday. Your team has mapped the vulnerability, but your threat intelligence team detects early indicators of unauthorized scanning attempts hitting your perimeter. No breach has occurred and no data has been exfiltrated. But your corporate legal counsel is asking if this supply chain deadlock constitutes a potentially material cyber incident that requires preparing disclosure documentation. What is your move?
SPEAKER_01A okay, cool, cool. I was like, I know exactly what we're doing, but but let me let me hold for the multiple choice.
SPEAKER_00Okay. A proactive disclosure. Instruct legal to begin drafting an immediate SEC filing and notify flagship clients transparently to stay ahead of the narrative, risking market panic over an unexploited flaw. Okay, you're shaking your head no. B defensive non-disclosure, classify the event as an unexploited software vulnerability rather than a material breach. Focus entirely on internal remediation and defer any regulatory filings until a confirmed compromise occurs. Okay, that's looking good. C the vendor escrow play. Agree to prepare the documentation, but structure the filing to focus entirely on third-party systemic open source risk, intentionally shifting the accountability metrics away from your internal secure development lifecycle. And lastly, D, the quiet scrub, focus your team on quietly scrubbing and rotating all highly sensitive access tokens and PII caches currently sitting in application memory spaces trying to neutralize the potential blast radius before an exploit path opens.
SPEAKER_01We're definitely going with B. Um, in my opinion, um there is a time to do A, and then if if it's time to proactively disclose, then there's a time to do C. Um, and there's a time to kind of shift the blame, or, you know, however you want to say it, you know, one way to say it is you're shifting the blame. Another way to say it is to explain to folks how these different things happen. Um, you know, this is a supply chain attack, so there are dependencies involved. Um uh but yeah, I'm I'm definitely gonna go with if they're if the if the lawyer's looking to me to make a call as to whether I'm gonna call up the SEC and tell them that I have a material problem. Absolutely not until I'm sure that's the case. And I do not know right now. I don't know if I'm even uh affected. Um, and so there's absolutely no way uh that I would do that.
SPEAKER_00Okay, so you're going with the calculated silence.
SPEAKER_01Yeah, we're we're we are silent and we continue to investigate. Um, because it while it's possible that there is a ginormous material thing that should be reported to the SEC, if at some point we can absolutely confirm and validate that, then that's the right thing to do. We are not there right now.
SPEAKER_00Okay. Roger that, boss. Okay, here we go. Round three, the dashboard manipulation. It's Saturday afternoon. The chairman of the board reviews your security metrics, dashboard, and sees thousands of red flags. He panics because your primary competitor is preparing a hostile takeover evaluation on Monday. He tells you our evaluation cannot survive a systemic security failure right now. Downgrade the transistor dependency risk on the executive dashboard to medium until the weekend passes. Keep the raw logs accurate, but change the visualization colors. How do you respond? A the absolute technical veto, refuse to alter the dashboard presentation under any circumstances, state that data manipulation violates your professional code of ethics and prepare to resign if overridden. B. The contextual recalculation. Agree to modify the chart visualization, but explicitly relabel the metric as unexploited third-party exposure to accurately represent that no breach has occurred, changing the visual weight without lying about the numbers. C. The budget ransom. Agree to present a modified risk-weighted dashboard to the board only if the chairman signs a binding commitment to double your app sec engineering and technical debt budget starting Monday morning.
SPEAKER_01I mean, I kind of love that. Like if it works, but anyway, please continue. This is great.
SPEAKER_00D, the architectural pivot.
SPEAKER_01Oh, we're getting at least 10. Anyway, sorry.
SPEAKER_00The architectural pivot, refuse to alter the data, but pivot the presentation entirely away from vulnerability counts to focus on your active containment metrics, showing the board what percentage of the network has been isolated.
SPEAKER_01I love this question. Um I am not a sort of here here's how I look at it. If there's potentially a hostile takeover, and if they're examining our security posture, there are dozens of dimensions to that security posture. Uh the incident that we're talking about in the scenario is one out of thousands of other things that are going on that are that are effectively the same amount or probably like way worse. Like undoubtedly, there's something way worse than this going on. You know, I think about um I believe it was the previous question when it was like your perimeter is being scanned. Like, of course my perimeter is being scanned. Like, am I connected to the internet? You know, like, like, so I I think that um I think that for me I mean, I guess I'm I just I'm fascinated by C. You know, I'm fascinated by C. Um, like in what kind of a world can somebody get away with this? I don't actually think I could get away with it. So I'm gonna say not C, although, although it is, it is enticing because I do love the idea of a bigger security budget. Um I'm definitely gonna go for either B, which is contextual, sort of modify the chart. You know, I'm I'm a big believer that there's data and then there's a story. And how you present that data can greatly influence how that story is received and interpreted. Um, and as far as I understand from the scenario, we have not confirmed an active breach. Um we might be vulnerable. Um, and that does not need to be in any sort of cover letter. Um so I'm definitely going with um kind of a B or a D. And I think that, you know, if we're like a Fortune 500 company, more than likely we've got some sort of comprehensive risk assessment. Um, and while we, you know, uh there there's there's gotta be other data that's actually more reasonable to provide in a situation like this. Right, right. There's no Yeah, there's just no there's just no reason to focus on this enormous question mark uh that we have in this point in time.
SPEAKER_00Okay, okay. So you're looking at more of like a flexible narrative.
SPEAKER_01Definitely flexible narrative.
SPEAKER_00Labeling things accurately, but having- Yeah, we're not I'm I'm not for lying.
SPEAKER_01Yeah, you know, I'm not for lying. I'm for let's look at the actual facts, let's look at the big picture, and let's tell the truth. Uh, that's what I'm for, which which could result uh if we're gonna go for the multiple choice in in either B or in D.
unknownD.
SPEAKER_00Okay. All right, we'll move to round four. We're making our way through it. The technical debt rebellion. Now it's Sunday morning. Your engineering teams have been working in a high stress war room for 36 hours. A group of principal developers pulls up an old architecture ticket from a year ago, showing you that flagged extinct.
SPEAKER_01Could have, did not, but could have.
SPEAKER_00Those things exist, they come back to bite you. The showing you that flag flagged that the technical debt of relying on your underfunded logback extension library, but deferred the refactoring project to meet commercial feature velocity targets. They're exhausted. They threaten to pause remediation efforts unless you publicly acknowledge that the company's metrics program structurally prioritizes speed over stability. What is your move? A. The accountability town hall, hold an intimate, unscripted call with the engineering wing, explicitly own the historical backlog prioritization mistake, take personal accountability and commit to shifting your core metrics toward architectural health. B the instant command mandate, remind them that the war room is under emergency instant command structure, defer all cultural and retrospective debates until post-incident triage and command them to focus solely on the active mitigation. C the financial retention injection, bypass the cultural debate by offering an immediate, significant crisis delivery bonus.
SPEAKER_01Oh my gosh, where does all this extra money come from? I just I love these scenarios where there are just like pots of money available for the taking. Um, love it. Please continue.
unknownOkay.
SPEAKER_00Yeah, you get a car, you get a car. Um, crisis delivery bonus to the engineering team to cross the finish line, delaying the retrospective entirely. And lastly, D, the shared accountability spin, reframe the narrative by explaining to the developers that the flaw isn't a failure of internal prioritization, but a systemic failure of global open source software sustainability that no enterprise framework could fully mitigate.
SPEAKER_01So I'm definitely gonna call and talk to these people. Um they they need to be heard out, right? Um they're feeling emotional, they're exhausted, they feel like this could have prevent been prevented. Um, and in a leadership position, I I need to call these people and I need to talk to them. They need to be heard. Um, I think that's extremely important. Um again, where is this like mystery bonus coming from? Like, shouldn't we have just fixed it? Like when they told us to fix it a year ago if we had all this extra money. Anyway, so C is out of the picture, I think. Um you know, I think, I think D, which is the shared accountability, there's a recognition that that that we can discuss that says, look, this is the this is the state of global enterprise software today. Um and and ultimately we need to get back to B. Ultimately, we're in the middle of an active incident. Don't quit me wrong, I'm never gonna let a good incident go to waste. I'm actually gonna try, once we address the incident, to squeeze as much money as culturally possible to get it. Um, but now is not the time. Uh, and so we've really just got to focus on instant command. I want to hear these folks out. Uh ultimately, uh, my choice is is gonna be B.
SPEAKER_00Okay, okay. So pulling rank in the middle of a crisis.
SPEAKER_01You're do your freaking job, people! Do your job. You are working for a Fortune 500 company, do your job.
SPEAKER_00But but then you you run the risk of potentially uh a toxic cultural feature.
SPEAKER_01Oh, we've got that already. Don't you worry. This is a Fortune 500 company, right? I mean, people people are already pissed, you know, and and I can look like if it gets resolved beautifully, you know, then then maybe at sort of performance evaluation time there's an opportunity to say, hey, these folks really stepped it up, you know, but it's not sort of this right, right. I mean, there it's it's not sort of this like, oh, I have this mystery $500,000. It's just like sitting around. I might as well freaking pay the ransom. We're not actually paying, we're not actually paying. But but um, but I but I do enjoy I do enjoy having that as a possibility.
SPEAKER_00Oh no, I love that. I love that as a post post toxic workplace already there.
SPEAKER_01Don't even worry about it.
SPEAKER_00Yeah, good luck. Let me know when you walk into a perfect perfect environment. It's never that way. Something's always hiding behind the scenes. Um okay.
SPEAKER_01Not at this scale, right? Tiny startups, maybe. Enormous global enterprises, Fortune 500.
SPEAKER_00Yeah, good luck for that. For downtime is not an option. Yes.
SPEAKER_01Yeah, there's it's just yeah.
unknownOkay.
SPEAKER_01This is the job. Do the job.
SPEAKER_00Round five, the 72-hour climax, the logic containment. It's Monday morning, the 72-hour deadline is expiring, and the maintainer has not received his funding pool. Scans against your platform are peaking. Your AppSec team presents an unvetted experimental runtime hot patch that uses monkey patching to intercept and neutralize the specific vulnerable function calls inside the memory. It has an 80% chance of stabilizing the flaw, but a 20% chance of causing state deserialization corruption across your primary transaction databases. What is your final command? A, do it live, authorize the deployment of the experimental memory hot patch. We accept the 20% risk of data corruption to eliminate a known critical RCE threat before the markets open. B the layered containment, reject the unstable patch, rely strictly on your layered network segmentation, aggressive cloud security groups, and service mesh throttling to catch and contain the exploit attempts, accepting that some applications may fail gracefully. C, the sustainability contribution, direct your executive team to pay a hundred thousand corporate contribution to the maintainer sustainability fund alongside other enterprise users to secure the official patch. Uh sorry, yeah, to secure the official patch. Safely. D, the hard feature amputation. Run an automated script to aggressively strip the logging module out of your containers entirely. This will break user metrics, logging, visibility, and 80% of your customer facing deaths or features, but it leaves your core database records 100% secure.
SPEAKER_01I need to uh review a couple of assumptions. So I think that we've got an assumption that someone on my team on my side has confirmed that this thread is like for real. Like some somebody has confirmed, like, this is absolutely real. Like, this is for real RCE. This is not like at this point, that's been confirmed. Like, it is gonna happen. It's gonna be bad. Um, I actually do think that before this point in time, we would be engaging with sort of peer firms. We would have like kind of reached out to a network of CISOs and said to folks, like, hey, we need to, we need to coordinate, right? And and and that doesn't necessarily mean we're all gonna pitch in and and pay the 600k, um, but we are all in a scenario that gives us an opportunity uh to work together. So my my my hope and expectation is that those uh conversations started sort of on day one. Um I'm kind of into uh B, you know, I like this sort of layered uh networking approach. Um I I I don't love A only because it seems um like here's the thing about like random brilliant appsec people. Like sometimes they're brilliant and they're right and they save the day. And then other times they're not. And like at this point in time, like I I just have no way of not worth 20% gain. Um D is also not bad. D is also not bad. I think that there is some information that matters more than others. I do care more about my core database records than I do about like relatively peripheral sort of visibility and and logging. Um, so I'm finding myself a little bit B, a little bit uh D if we for sure know that this is absolutely gonna result in uh RCE, unauthorized access.
SPEAKER_00Okay, okay, okay. All right, so it sounds like you're leaning a little bit more towards B, potentially, with a little bit of help from so you're betting on company's integrity on the perimeter and the network isolation controls to do I really think they're good.
SPEAKER_01You know, I think that I don't think they're good. I I I think I think I think if I could choose two, it's B and D. If I could choose one, it's D. Get it out of there. If you can get it out of there without causing damage to the core database, get it out.
SPEAKER_00Yes, yes.
SPEAKER_01And we'll deal with whatever happens after. I mean, I I don't I don't love castrating our application layer. What a what a what a great word. I I I intentionally didn't make a side comment about the 72-hour climax, um, but maybe we'll get into that uh in Vegas. Um okay, so clarification. Uh option D is the application rendered unusable? Like, can users not use it? Because that would be a big problem.
SPEAKER_00That we don't necessarily specify.
SPEAKER_01Okay, it's not specified. Yeah, so um so given given, you know, kind of the parameters of the game, uh, I'm going for D. Pull it out, save the database. Who cares about extra logging? Let's prevent this RCE from happening.
SPEAKER_00Let's do it. All right, so now we're gonna recap.
SPEAKER_0172-hour climax.
SPEAKER_00So that clock has stopped.
SPEAKER_01I didn't write the script.
SPEAKER_00Take fun for that.
unknownI know.
SPEAKER_00Your production environment is either running under constrained isolation or your database is choking on an unpatched memory exploit. You've just watched a global tech stack hang by an open source thread. Caroline, you faced a supply chain strike, an SEC puzzle, and uh dashboard pressure from or sorry, yeah, dashboard pressure from the board and an engineering mutiny. Before we reveal your score, I have to ask, you do get everybody gets scored. Yeah, don't worry, nobody's nobody's gotten 100%. Um did you miss the days when application security was just about running a clean static code scan where risk was a predictable metric on a screen versus a human being walking away from a repository.
SPEAKER_01Yeah, I mean, I I it's it's never it's never been that unfortunately, right? AppSec was never simple. Um we're we're on the cusp of AppSec in the AI era. Like, what even does that look like? We actually have no idea. Um, but I'm in this industry for the chaos and for the fun and for the high pressure. So, you know, I'm here for it.
SPEAKER_00Yep, yep, never ending, right? So we're gonna go with based on how you answered, um, the strategic architect. You've got balanced risk and pragmatic defenses. You handled the you handled this like a true systems thinker, and you balance the board's anxiety against real-world blast radius management, relying on layered containment, um, your team's visibility and service meshes rather than silver bullet patches, um, aside from the amputation.
SPEAKER_01Cut it off, cut out the cancer, get rid of it. I don't care, you don't need that leg.
SPEAKER_00You'll still function. It's okay.
SPEAKER_01You'll you're gonna stay alive. Let's let's focus on let's focus on staying alive.
SPEAKER_00Yeah, you manage the metrics and you didn't let them manage you. So you get a score of 88 out of 100. Congratulations.
SPEAKER_01I'll take it. I like that. Chinese people love the number eight, so that's like I'll I'll this is extra extra bonus points. Even better. Okay.
SPEAKER_00I did not know that. All right.
SPEAKER_01Yep, yep, fun fact.
SPEAKER_00Okay, before we unlock you out of the hot seat uh and let you out of the zone, we have one final question that we ask every elite security pioneer who survives the crucible. Caroline.
SPEAKER_01The script is so good. I need to know the name of your writer. We can talk about it after. This is really awesome.
SPEAKER_00You've dedicated your career to the pursuit of visibility, scaling, uh, it's scalable engineering frameworks and data-driven security metrics. You have helped shape how a generation of absec professionals views code safety. But we saw today the supply the software supply chain is ultimately built on human trust, human fatigue, and systematic vulnerabilities that a spreadsheet can't always predict. If you could send one sentence or your thoughts, cryptographically signed message back through time to your 22-year-old self, starting out in your first tech role, what would it say about the balance between the data we can measure and the human chaos we cannot control?
SPEAKER_01The humans are always the least predictable, and all the biggest problems come from the people and the decisions that they make. Um yeah, that's a little depressing. I mean, I wonder if I'm allowed to tell my 22-year-old self, like, go to medical school. Just totally kidding. I actually I love this industry. AI is gonna be great. Uh, Christine, thank you so much for having me.
SPEAKER_00Okay, I'll just I'll okay, that's awesome. I'll do a quick wrap. Um, and that's a wrap on the episode, on our episode of Hack the Boxes Pressure Zone. To our listeners in the engineering and executive suites, remember that your software bill of materials might look flawless on a dashboard and your compliance gates might all be green, but your modern application architecture is intimately connected to a global open source community. That's right, that requires sustainable support, visible prioritization, and strategic technical debt management. Your code is only as strong as the most invisible link in your dependency tree. Um, so make sure to actively manage your software foundations, or someone else will.
SPEAKER_01Or someone else will. Or someone else will. I I gotta tell my 22-year-old self, um, you should probably just get into jujitsu right now. Because every once in a while you're gonna you're gonna burn out, you're gonna need some stress relief, you're gonna spend so much time in front of a screen. You just gotta get physical and master of fighting sport.
SPEAKER_00Get it out. Yeah, hey, this is why I run, you know?
SPEAKER_01So I yeah, I feel like yeah, we are we are physical creatures, right? Like do stuff with your body too. We are not just brain blobs in computers, like typing on a machine. Move your body, move your body, totally, totally.
SPEAKER_00Okay, so join us next time. We bring another global technology leader to the hot seat and see if they can survive the crucible until then. Track your data, respect your engineering pipelines, and watch your dependencies. Thank you for joining the HTV Pressure Zone Podcast.
