CyberWire-X 4.19.20
Ep 5 | 4.19.20

Complementary colors: teaming tactics in cybersecurity.


Dave Bittner: [00:00:04] Hello, everyone, and welcome to CyberWire-X, a series of specials designed to highlight important security topics affecting organizations around the world. We often hear cybersecurity professionals talking about red teams, blue teams and purple teams. In this episode of CyberWire-X, we explore what those terms mean, how security teaming approaches have changed over time and the value of teaming for organizations large and small. The first part of our show features a lively conversation with our experts, Austin Scott from Dragos and Caleb Barlow from CynergisTek. In part two, we'll hear from Dan DeCloss from PlexTrac, the sponsor of today's episode. Stay with us. 

Dave Bittner: [00:00:49]  And now a word from our sponsor PlexTrac. PlexTrac is the ultimate purple teaming platform, guiding the healthy collaboration of your red and blue teams through a single web-based interface. PlexTrac does this by first elevating red teams, eliminating the struggle of reporting and allowing the team to focus on what's important - identifying security issues. Red teams are provided with an easy-to-use platform that allows reports to be created and then exported with a click of a button, saving the team valuable time. PlexTrac also powers up blue teams by providing them with a platform to consolidate findings and then remediate them in an efficient and timely manner. Gone are the days of 500-page penetration test reports as PlexTrac streamlines the process with a status tracker, integrations with ticketing systems, dashboards and analytic capabilities and much more. You can visit their website at to learn more. That's And we thank PlexTrac for sponsoring our show. 

Austin Scott: [00:01:59]  Red teaming - I believe it comes from military jargon, where you are doing adversary simulation. 

Dave Bittner: [00:02:07]  That's Austin Scott. He's a principal penetration tester at Dragos. 

Austin Scott: [00:02:11]  And, of course, within cybersecurity, the definition of that changes depending on who you ask. And, I mean, I don't want to start a religious war or anything like that here, but I can talk about my definition of red teaming. So a red team, of course, is an adversary simulation where you're trying to identify risk in the network. You're looking at a network from an adversary's perspective. So at the end of the day, you're trying to identify if an adversary, when they're faced with your network, if it's an unsurmountable, unclimbable marble wall or if they can cut through it like a hot knife through butter. So this can really help you identify ways you can protect, detect and respond to cyberthreats through this sort of simulated adversary. 

Caleb Barlow: [00:03:01]  Can the red team get around that two-factor authentication in some way? 

Dave Bittner: [00:03:06]  That's Caleb Barlow, CEO at CynergisTek. 

Caleb Barlow: [00:03:10]  Or can they validate that it's working? Or can they find a place where maybe a system that is not in place, and it should be? So, you know, a lot of the resourcing on this is going to be directly derived from either controls that you want (ph) to validate and test, or it can be looking at areas where you know you have a vulnerability - because I'll tell you, in most security assessments, there are large numbers of vulnerabilities or known issues that get identified, and nobody has the budget to fix all of them. But what you can do is you can say, well, what are the odds of this being exploited? 

Dave Bittner: [00:03:48]  Now, how about blue teaming? What's involved there? 

Austin Scott: [00:03:51]  Blue teaming is the opposite side of the fence as red teaming. 

Dave Bittner: [00:03:55]  That's Austin Scott from Dragos. 

Austin Scott: [00:03:57]  Blue teams are the network defenders. They're the guys who are trying to protect and detect and respond to the adversary. With a red team exercise, there may be a blue team present, or maybe it would just be the normal SOC operations team. They may be aware or they may be unaware that the red team will be doing an exercise or is working to compromise their network. 

Dave Bittner: [00:04:23]  So red plus blue equals purple. How do you define purple teaming for folks? 

Austin Scott: [00:04:28]  So a purple team is much more of a collaborative approach. It's where the red team and blue team are working together to identify gaps in cyberdefenses. 

Caleb Barlow: [00:04:41]  The difference with a purple team is you're informing yourself of the vulnerabilities in the knowledge on the inside. 

Dave Bittner: [00:04:49]  That's Caleb Barlow from CynergisTek. 

Caleb Barlow: [00:04:52]  So you're giving that team the opportunity to say, hey, we know we might have some problems in this area. Can you expose them? And that might be to prove positive that a defense is working or prove negative that it's not working. 

Austin Scott: [00:05:09]  So in a purple team exercise, you might have the red team and the blue team all in the same boardroom, and the red team will be going through their exercise in a very transparent way. It'll be a much more of a white-box approach. The red team is sharing information with the blue team, and the blue team is sharing information with the red team. So as they're working through a network, a red team member might tell the blue team, we're going to try this particular attack; we're going to run this script, and tell me what you see. 

Austin Scott: [00:05:38]  And the blue team will look. They'll check their security operations center and try to understand what's going on, see if they can detect and respond to that. And in my experience, in these purple team exercises, the blue team can even tune their detections in real time. They may get us to fire an attack multiple times so they can adjust their detection mechanisms to better defend their network. So it's a much more collaborative approach to penetration testing. 

Dave Bittner: [00:06:08]  And I suppose it sort of takes away that even friendly adversarial relationship that I imagine could form between the two teams. 

Austin Scott: [00:06:19]  Yes. That's very true. When you take an adversarial approach, you're inherently kind of working against each other. So the opportunities to share knowledge and to grow kind of as a team aren't really there, where, when you're working together, collaborating in the purple team, you know, the blue team gets to learn a lot about the red team tactics, and the red team learns a lot from the blue team tactics as well. So there's a lot more opportunity for cross-sharing and team building as well. 

Dave Bittner: [00:06:46]  When you're doing these sorts of exercises, is there an opportunity to gain some insights on where you should be putting your resources? In other words, you know, hey, it seems like our defenses are good - or maybe not. Or our defenses are really good, and we need to focus more on trying to chip away at them. 

Austin Scott: [00:07:09]  Absolutely. Any one of these red team or purple team engagement or type exercise will identify those gaps in the network. And this is something that you can't really necessarily get from, like, a vulnerability assessment or a Nessus scan or something like that because, you know, tools like that or approaches like that that are just terrifying vulnerabilities don't really take into consideration the human factor or misconfigurations in the network or weaknesses in network architecture. It doesn't take the bigger picture into account, whereas when you're doing these exercises and trying to move through a network as an adversary would, you're really taking all things into account and trying to leverage any weaknesses you can find, including the people, which are usually the weakest link in any security paradigm. 

Dave Bittner: [00:07:57]  What sort of recommendations do you have for organizations that are looking to put together their red teams, their blue teams and then foster this communication to make purple excel (ph)? 

Austin Scott: [00:08:09]  Well, I do recommend taking a purple team approach where possible, especially if you're just kind of getting started. I think the biggest opportunities to grow and learn and to expand knowledge come from purple team exercises, whereas a pure adversarial assessment, like a red team, you don't really have many of those opportunities. You'll definitely get a report at the end of the day, but you don't really see what the attacker was necessarily doing during the entire engagement, and you wouldn't have opportunities to tune or learn as you go. 

Austin Scott: [00:08:43]  And also, I found that the red team won't find as many things because, usually, the blue team or the - you know, the local resources know where all the skeletons are buried, and they know where to look for a lot of these vulnerabilities. So if you can enlist the blue team into your red team, you get a lot more value. Often, the blue team is looking for resources. Often, they want you to find these things. They want to identify the risks that they already are well aware of so that they can justify the expense of solving these problems. 

Dave Bittner: [00:09:14]  Yeah, and at the end of the day, we're all on the same team. 

Austin Scott: [00:09:18]  That's right. Yes. 

Dave Bittner: [00:09:19]  When you're coming at these sort of exercises, how much of it is sort of episodic, where you spin up, you go through this exercise, and then you're done, and you evaluate what has happened, versus an ongoing effort that's sort of continuous? 

Austin Scott: [00:09:37]  Where I've seen the more episodic approach is as a consultant. We usually have a plan - a daily plan of where we want to be or how we want to progress through the network. And we can move a lot faster with this approach with a purple team or a more white-box approach, you know? If we don't get to where we need to be on day one, then we'll move to the next episode. We'll move to the next network segment and kind of see what the network looks like from that perspective. This way, we can - even if we can't advance, even if we run into issues where we're unable to move through the network because the security posture's really strong, we can still jump around the network and sort of see - shine our flashlight into some of the darkest areas of these networks and see what they might look like from an adversary perspective. 

Austin Scott: [00:10:22]  But for a continuous program, I've seen organizations that have dedicated red teams that will continuously run operations and run programs and usually keeping the SOC in the loop as well, letting them know that these things are ongoing and to look for activities in various networks. So certainly, it's something that an organization could benefit from, having that run continuously. There's always been this sort of inherent challenge between the IT folks, and cybersecurity folks, and the operational technology folks and the engineering folks. Any opportunities to build bridges between them and to get everyone in a room to work together is a real win for industrial cybersecurity. So we find these exercises are a great opportunity to get all these folks together that don't normally work together, that don't necessarily trust each other to address these issues and identify these risks. 

Caleb Barlow: [00:11:20]  At the end of the day, what you want to do is, you want to incent people like an adversary would be incented. You want a little bit of a prize if they can pull it off. 

Dave Bittner: [00:11:29]  Caleb Barlow from CynergisTek. 

Caleb Barlow: [00:11:31]  And, you know, that prize might be driven by a little bit of bravado. Or, you know, maybe it's a box of donuts. I don't know. But either way, I do think there's an opportunity there. And, you know, there's a good example of - many of your listeners may have heard of this concept used in development called the Chaos Monkey. And I think this was originally pioneered by Netflix. I know they use it pretty heavily. And the idea was, a development team is going to infuse chaos into their operational environment every so often and see if the tools, the hardware and the operational team can deal with that chaos, right? 

Caleb Barlow: [00:12:11]  You know, so a certain amount of downtime, if you will, in production was going to be driven by events you caused yourself. Maybe you're going to take down a data center or take down a server and make sure your resiliency efforts work. You know, one of the things you see security teams doing now is using this same concept of a security monkey internally to effectively cause their own security issues and force their teams in production to respond to them. And of course, the team that's responding has no idea if it's real or if it's the Chaos Monkey. 

Caleb Barlow: [00:12:45]  And it's an example of a purple teaming-type activity that I think can be very effective because it gives you the ability to constantly exercise those SOC teams to know, hey, can we detect this certain vulnerability or this certain type of malware? Do we get the right response to it? But more than what you'd have on paper, how fast was the response? Did it get escalated in the right way? Did it get disposition properly? Was it documented properly? All of those things you can ask to really make sure you've got that muscle memory in place. 

Dave Bittner: [00:13:18]  Right. So it can provide justification for spending or focusing more resources on that issue. 

Caleb Barlow: [00:13:25]  Exactly. So my point, Dave, is, it's not just about the people. It's about what's your overall spend? Now, I think the other thing we have to keep in mind is, everybody, based on the last few weeks, should pull their security assessments and say, OK, what just changed as the world changed with coronavirus? The threat landscape changed in that adversaries are now, you know, targeting specific activities and kind of phishing emails around coronavirus. But also, I now have my entire workforce outside the firewall and working from home on who knows what device. 

Caleb Barlow: [00:14:01]  How does that change this assessment? Are there new risks here that weren't here before that I need to think about in a new way? Maybe I should purple team that. Or, worse case, if I can't fix the issue, I should at least go build a run book so that if it is exercised, I'm prepared to respond to it. I think purple teaming is the next thing for people to start to really look at because if you think about it, we've all stepped forward in front of our CEO or board and said, hey, I need to buy this really expensive security product. Well, OK, how are we going to measure the return on that? Well, I don't know. If it works, nothing will happen. 

Dave Bittner: [00:14:46]  Right. 

Caleb Barlow: [00:14:46]  And that's a really hard sell. One of the other advantages of purple teaming is now you're able to go forward and go, hey, boss. We have this vulnerability. We kind of pointed this to our purple team who went and tried to exercise it. It took them 15 minutes, and they were able to get into everything. I think we really need to go buy this tool that's going to stop that. That's now a totally different value proposition. 

Dave Bittner: [00:15:24]  Next up, we hear from Dan DeCloss, founder and CEO at PlexTrac. They're the sponsors of this show. 

Dan Decloss: [00:15:33]  So the blue team being those folks that are responsible for defending the organization, protecting the crown jewels of an organization and responsible for deploying the entire security program within that organization - that's what we would say is traditionally considered the blue team. The red team in the traditional sense is very focused on penetration testing and even deeper diving into the techniques and tactics that an attacker may have. But for our perspective, we abstract that out to be anything that's proactive, anything that is somehow related to the proactive assessment of security control, so not just the penetration testing activities, but anybody that's conducting a risk assessment or a questionnaire or a gap analysis. The proactive assessment is anybody that's doing something to identify a security hole in the infrastructure. 

Dave Bittner: [00:16:28]  Now, are you on board with this notion that purple teams aren't necessarily teams, that it's more of a concept rather than actual people assigned to things? 

Dan Decloss: [00:16:38]  Yes, absolutely. I mean, we actually call it the purple paradigm - right? - or that it's a paradigm - you know, that purple teaming itself is not a specific job function, but it's a role that everybody plays. So it's really meant to be that mindset that we're all on the same team, and we're all collaborating to improve the security posture and be able to collaborate more quickly and effectively and truly identify the major risks that should be focused on on a daily basis. So it's not a specific role. It's not a specific job function but something that is more, everybody's a part of the purple team. 

Dave Bittner: [00:17:15]  You know, I can imagine that your red teams and your blue teams might have a healthy amount of competitiveness between them. But I suppose part of what you're after here is that you don't want that to turn adversarial. You need to put the tools in front of them so they can remain collaborative. 

Dan Decloss: [00:17:33]  Yeah, exactly. I mean, though, at the end of the day, we're all on the same team, trying to achieve the same mission, and that's to protect ourselves against the adversary, the true adversary. So it's not meant - you know, purple teaming itself is not meant to be this pitting the red team against the blue team, and no one's sharing the techniques that they're using. And then at the end of the engagement, you know, they plop down a 300-page report that shows all the weaknesses that you have, and now, you know, good luck going to try and fix that, right? 

Dan Decloss: [00:17:59]  That's the - you know, that's potentially - you know, some people kind of used to do it that way. And so we want to avoid that by saying, hey, you know, we're on the same team. We're all trying to collaborate. And at the end of the day, we want to identify compromise as quickly as possible and as early in the attack life cycle as possible, so making sure that everybody understands that this is the true mission and this is how we make progress instead of having to just get more tools that hopefully automate - I mean, obviously, we're always kind of focused on automation. But there's a lot of manual effort and a lot of efficiencies that get lost. And so we really want to focus on having those teams collaborate together in order to streamline the process and make sure that things are getting fixed quicker and that time is spent on the actual cybersecurity work getting done. 

Dave Bittner: [00:18:52]  Yeah. And it seems to me like, by having it be dynamic in that way, that information is being shared back and forth, you know, in real time. I mean, that really does increase the efficiencies of both teams. 

Dan Decloss: [00:19:06]  Yeah. Absolutely, you know? And I mean, this was a pain on both sides of the fence that I live. You know, I was a penetration tester and hated writing reports. And you get to the end of an engagement, and it takes so long just to get all that information correlated and then put into, like, a Word document where you're - you know, you're spending a lot of time dealing with different formatting issues and all that jazz. And then you deliver it to a customer. Or, you know, even - I was on an internal team, so, you know, we're delivering it to the other departments. And then you just don't know what's going to happen to it, right? 

Dan Decloss: [00:19:37]  A lot of times, it gets put on a shelf, or, you know, some of the things get extracted and put into a spreadsheet or some other kind of tracking system. So you lose a lot of work, and you lose a lot of visibility. And so then from the blue team's perspective - you know, I built out a blue team and helped build up that capability for an organization. And, you know, what are you supposed to do with a really big, you know, Word document that's a pen test report or some other kind of security assessment, whether it's a PCI audit or something like that? So being able to have all that data in one spot and being able to quickly remediate those issues speeds up the process so much and really keeps the focus on, here are the things that we know we have to work on. 

Dan Decloss: [00:20:18]  And then also, you don't lose that data over time, right? So you can start to identify trends. Like, hey, we're consistently finding issues related to sequel injection or, you know, lateral movement. And how do we start to identify what areas we need to invest in to improve our security posture and our maturity over time? 

Dave Bittner: [00:20:38]  It's interesting to me that with each of these teams - your red team, your blue team or your purple team - at some point, you're going to have to do reporting. And it strikes me that particularly when you're reporting to the board, there could be a certain translation layer that has to take place there. 

Dan Decloss: [00:20:55]  Yeah. So, I mean, when I was a security director or the equivalent of a chief security officer today or information security officer, one of the challenges I had was being able to draw metrics from all the different tools and being able to present a clear picture of, like, the progress that we've made. And you can categorize them based on business unit or industry, all those types of things, so that you can really slice and dice the data the way that you want to be able to show the picture of like, hey, you know, maybe our business units - we want to have a little bit of a comparison between, here's who's trending in the right direction or here's who's not. And so that helps tell the story to the board of where that investment is going and where you feel the investment needs to get made for the next quarter or the next year. 

Dan Decloss: [00:21:43]  And you can also break it down across different clients or different constituents. So one example would be, you know, if you're involved in mergers and acquisitions, you could do some security assessments of the companies that you're acquiring and have a good idea of their security posture before you flip the switch to connect them or before you actually proceed with the merger. Same with on the insurance side - insurance companies can get a decent view of a variety of their clients or all of their clients from a central place and be able to start benchmarking and comparing. 

Dave Bittner: [00:22:15]  What's your advice to an organization that may be at the beginning of their journey when it comes to these things? Maybe not just red teaming and blue teaming, but this notion of purple teaming - they want to do a better job fostering that sense of communication. How do they begin? What sort of tips would you have for them? 

Dan Decloss: [00:22:35]  Yeah, good question. I think that definitely, you know, setting the mindset is important - right? - that we're all on the same team and we're all here to collaborate. So even setting up some small exercises where you can say, hey, we're going to just test one small thing - you know, I think some people start to get overwhelmed with that concept of, like, we've got to test the entire security posture. And my approach is to really take it in a much more iterative perspective so that, you know, you know it's kind of a - it's a marathon when building on a security program and improving your security posture - and so breaking that into a little, small chunks. 

Dan Decloss: [00:23:13]  You know, we love to reference the MITRE ATT&CK framework because it breaks down everything based on the attack life cycle, which, at the end of the day, that's what we're really trying to - you know, identify issues that are cropped up in each one of those different tactics. And so if you start there, you can actually focus on, like, just one small technique and say, like, hey, you know, we're going to test this out, and then we're going to work with you and collaborate closely on whether or not you identified that and what you need to do to fix it. So you kind of start to get in this quick feedback loop, quick iterative lifecycle for just testing small things and making that become the norm rather than breaking things into large assessments that take months at a time. 

Dan Decloss: [00:23:57]  I mean, you're always going to have that aspect, especially when we're talking about, like, an external assessment - but, like, within your enterprise and within your organization, breaking these things down and just identifying who's going to do the testing piece, who's going to do the remediation piece, how are you going to collaborate? And it doesn't have to be a specified role for either of those, right? You could have people that don't even have as much experience in it, and it starts to get them more exposure to the offensive techniques as well as the defensive. 

Dave Bittner: [00:24:25]  I'm curious about this notion of what I would describe as kind of load balancing, of - by using purple teaming to essentially connect your red team and your blue team to be able to look at the resources that are being assigned to each of those groups and the results that are coming out of them. Can you then take those results and use that to inform how you assign resources to each of them? 

Dan Decloss: [00:24:55]  Oh, yeah. No, that's a good point. I mean, yeah, you can definitely start to kind of get ideas for who's reporting more of different issues and those kinds of things. With people that are conducting, you know, red team assessments, they can immediately report those. And this happens a lot. But it's hard to capture - right? - in terms of, like, hey, we've identified something early in the engagement that we want to let you guys know about; they let them know about it; they fix it - can you retest it? - even before the engagement window is completed. And that's actually what we feel should be the norm - right? - is that as soon as things are identified, you can collaborate. You've captured when it was reported, so you still have all those metrics. And you're not losing the data as to, you know, the - if the - if it's a - say it's a contracted assessment. You know, did they did they find anything or not? I mean, that's going to be one of the big questions. And what did they do to conduct the assessment? You know, you can show that in real time. 

Dan Decloss: [00:25:49]  So you're not only fixing the issues faster, but you're still capturing all the metrics that you want from, you know, when it was reported, how you guys collaborated. And actually, showing that feedback is much more important because that's the value that somebody is going to provide from both sides of the fence. I think the important thing is, like, you know, for us, the purple team paradigm is really an abstraction, right? So a lot of times, people think of purple teaming as, you have this advanced red team that's going to sit down and - maybe even in the same room as the blue team, and they're going to just start running through things, which is still good. And that's still - you know, that's an important exercise. But abstracting the concept out to be much more collaborative at the, you know, general level from the red team being able to be anybody that's conducting any kind of assessment that identifies a security issue - that's one of the key things that we really try to hammer on. 

Dave Bittner: [00:26:51]  Our thanks to Caleb Barlow from CynergisTek, Austin Scott from Dragos and Dan DeCloss from our show's sponsors PlexTrac for joining us and sharing their expertise. CyberWire-X is a production of the CyberWire and is proudly produced in Maryland at the startup studios of DataTribe, where they're co-building the next generation of cybersecurity startups and technologies. Our coordinating producer is Jennifer Eiben. Executive editor is Peter Kilpe. And I'm Dave Bittner. Thanks for listening.