Red Teams

Ryan McGeehan
Starting Up Security
12 min readMar 30, 2015

When you can’t find the bad guys, make some up

You've spent money on security products that escalate nothing. You have a 24/7 SOC that hardly pays attention to their tools, or knows how to use them. You have intelligence feeds but have no idea what consumes them. Logs are inaccessible, slow to query, or non-existent. Defenders have stopped hunting and lost a sense of purpose.

That means it’s time for a Red Team to come in and fuck shit up.

Why Red Teams

High immersion, staged intrusions will exercise incident response capability in a way that further improves all facets of a security program. It’s possible to stage incidents that live somewhere between reality and drill. These exercises occur on our terms as Red Team designers, but are responded to as a real incident by a security response team (defenders).

Observe that professional athletes compete on a schedule. A clear schedule to hone their craft to peak at any moment. Defenders have no schedule. They are called to action by any number of adversaries at any time and expected to be at a constant peak or preparedness.

Likewise, it must be satisfying after training for a boxing match to finally punch someone in the face. So while putting millions into your company’s security, you better be damn sure you’re dusting off for a battle every now and then. Otherwise there’s no emotional or tangible reward for your preparation.

Previous Work

We ran four “live fire” Red Team exercises at Facebook, for two of which I can discuss the design decisions that mix story telling and realism with red teaming. Each one is named after the incident handling codename.

Red Team One: “Vampire”

We had a third party contracted Red Team take over our corporate Domain via a physically planted laptop that was hidden behind a cabinet, and connected to our network. The Red Team planners walked them right towards Domain Admin and chaperoned their access afterward. This allowed (supervised) lateral movement, malware, and exfiltration.

Let’s be very clear: to get the Red Team beyond “defense in depth”, we placed them behind defenses they’d normally have to breach. Without this it would only be a penetration test. This is cheating, and is OK.

An effective exercise must take you through a worst case scenario. Cheating helps you get there in reasonable time. It’s about the final production.

With this access, the Red Team then impersonated one of our greatest historical adversaries and threatened our security team for ~24 hours with terrifying extortion emails. This placed our team into a worst case scenario situation appearing as if the only mitigation was a complete wipe of corporate IT from servers to laptops. Defenders weren’t given a heads up about this exercise. They had to deal with it anyway.

Yep.

During the response, we had to “cancel” vacation plans, calm panicked employees, and negotiate the tough decisions around production system shutdowns. Defenders were tasked with building a recovery plan which considered how much, if not all, we’d have to be rebuild. This is a significant amount of the headache you deal with when you’re really in the thick of a worst case intrusion, and has little to do with forensics or IR.

Next morning, we broke the news to the team that this was a staged (albeit real) good-guy intrusion. There was long silence, red faces, and we were doing a lot of explaining. I wasn’t sure how the team would react. A former FBI agent we hired to do malware research broke the silence with a “…Then that’s fucking awesome!” and the room lit up.

Someone then reminded the room that it was April Fools Day.

Even after explaining, several defenders came up to me saying “but we found real and unknown malware” so that “it must have been a real incident”. They were in temporary disbelief when we told them we had malware custom written for the exercise to add to the realism. People showed up late to this meeting, which caused a lot of awkward laughs as we had to break the news to every late arrival in front of everyone over and over.

That evening we had plans to take the team to a bar to decompress. They were a bit dazed for a day or so, but were absolutely pumped about the future. We now had a group of defenders who have been through the stress of a worst possible breach, together. That experience is invaluable.

Vampire murdering trophies for impactful incident responders

We rewarded the contributors of the incident response with these “Vampire” Stakes and let them know we were proud of their response. The rest of the week was cleanup and post mortem, all very calm and settled.

Deep relationships were formed between the Security and IT teams because of the shared experience. There was also a new level of empathy from IT towards Security’s goals after experiencing how bad a full intrusion could be for the company.

Evolving the Exercise

It was very clear that Facebook wanted to continue these exercises after experiencing a terrifying incident firsthand. There were three more comprehensive exercises in the years afterward, while I was there. These were some of the big parts of the exercises we’ve made public:

  • We made use of a browser zero day that was used to give a Red Team access to an engineer’s laptop (While we disclosed it to a vendor).
  • A former employee sat in on the Red Team, to simulate some “insider” knowledge an APT group may gain over prolonged access.
  • We asked the FBI to give us a the equivalent of a breach notification to kick off an unannounced exercise.
  • Larger production systems were added to the scope of exercises, increasing risk of a damaging mishandling.

My team was fully aware of the amount of resources we’d put into these exercises based on the previous two rounds, and knew that future exercises would involve new firepower (or we wouldn’t be doing them). They all involved strategic cheating, exploits, lateral movement, and some high value target at the end of it.

The Window

In later exercises, we announced a two month time window when these Red Team exercises would take place at, giving FB Security their “bout” to train for. This was different than being totally unannounced, like Vampire. This tiny detail was an 100x lesson for me related to Red Team design. Telling the team when the incident could happen had a hugely positive side effect.

For the month leading up to the Red Team window, the team leaned towards obsession. IR Weaponization occurred. Old tools were dusted off. Comprehensive training. Re-calibrated paranoia. They wanted to beat the Red Team instead of a faceless, description-less adversary that might not even exist. Everyone wanted their contribution to be the one that caught a massive Red Team exercise.

As a result, our prevention, detection, and IR momentum increased beyond our measure at the time. We hit an even higher security peak that lasted beyond the exercise.

The Box

We gave the Incident Response team a theme to follow:

One Lead is All You Need

This means that after an intrusion is discovered from a single IOC, all lateral movement should be discovered if our response capability is strong.

To symbolize this, we gave responders a wooden box. The box had 10 or so wax sealed envelopes. Each envelope had an IOC that the Red Team knew about. The response team could open them whenever they needed to move things along, the goal being to open the least amount possible. This was mostly used as a time box for the game, not any measure of success. But it became a point of pride for the team to open the least amount possible.

Almost all of the IOC’s were discovered through our existing forensic and monitoring tools. This was a strong sign that we’re getting better as we probably wouldn’t have discovered them all years earlier, or at least as quickly.

Puzzle Pieces with IOC’s etched into them in envelopes to gamify the IR process

Some envelopes had a “black spot” from pirate lore, which meant that the responder had to sit out and show another team member how to respond in their place. For Red Team Four, we used puzzle pieces.

Red Team Design

These influences were important in designing the four exercises.

“Game Master”

You need someone running the show, preferably the one who designed the exercise. This role talks to the Red Team, the Defenders, as-senior-as-possible leadership if things get wacky. They’ll make judgement calls when the Defenders need to ask the Red Team a question, and whether it’s allowed to be answered. It’s very likely that the defenders might find a real compromise, and will need to ask the Red Team whether it was them or not.

The Game Master should hold the Red Team accountable for their notes. Making sure they have detailed record of their intrusion is pure gold for follow up, and comparing how well the defenders discovered their badness.

This role should also be very sensitive to issues around panic, shaming, and generally how much effort and exhaustion is building up from the responders. They should have strong relationships to the organizations that manage PR, legal, any sort of law enforcement outreach, etc.

Alternate Reality Games

An goal of an ARG is to partially buy into an overwhelming fictional experience. I did my best to design Red Teams to have a sense of realism to them, even if they were fictional.

If you’re not familiar with ARG’s, there are many lessons to be pulled from them. It’s most important to have participated in one and understood how it can sort of wash over your normal day to day. I personally had a lot of fun with The Jejune Institute in San Francisco, but there are many online ones as well.

While participants should feel the urgency of a real incident, it shouldn’t feel so over the top that they can’t function. You want your team to stretch their incident legs with this experience, so that any future incidents run much smoother.

Panic

It’s important to manage a healthy amount of urgency, reasons to panic, and actual panic in designing an exercise.

Don’t make physical threats part of an unannounced exercise. That goes too far. Even with an announced exercise, it could go screwy.

Vampire was high panic because it was unannounced. We didn’t allow the drills to run more than 24 hours without an “all clear — this was a drill”. They were extremely stressful this way. We would not let fully immersive drills go longer than 24 hours.

Announced exercises involving a window were able to develop panic for several reasons despite being announced. The first was that large networks and production systems were put at actual risk, due to the potential of botching the IR. Second, everyone wanted to discover what sort of new capability would be used, and be the one to catch it. So despite it being real panic — emotions and enthusiasm were positive.

Gamification

I didn’t want to gamify things too much to deter from realism, but The Box was a very important tool to prevent these exercises from becoming a months long exercise. Real intrusions can easily become that long and painful. Each envelope served as a series of wins — opening an envelope and finding an IOC that was already discovered was a reason to celebrate. It kept momentum going, which is satisfying for a responder.

Other than that — it was important to use our real tools, defenses, and systems in the exercise. None of that was pretend or table topped.

Rewards

Red Teams are a terrible way to find under-performers and a great way to find rockstars. Because of the high amount of stress, there has to be a high amount of reward as well. Be sure to celebrate a Red Team season and have fun however possible.

Red Team Cheating (Fourth Wall Sabotage)

Real adversaries have unlimited time and we do not. We have to force the Red Team’s intrusion quickly.

So we have to cheat!

Give the Red Team important passwords. Walk them through doors, hand over design docs, or outright share a vulnerability they can exploit. Cheating effectively creates an incident to respond to, which is more important than finding actual vulnerabilities for our purposes of improving response and empathy towards security among participants.

This goes strongly against the use of a Red Team as an assessment tool. Remember — this is an exercise to improve full incident response and empathy towards security. I would argue that this more effectively improves actual security. Focusing strictly on assessments builds a policy of never-having-a-vulnerability. When measuring risk, there are no denominators to comfort you.

Positioning

Observe the kill-chain when designing an exercise and consider each milestone for realism. Billion dollar adversaries do not shoulder surf their way into your company, so imitate realistic scenarios for better panic.

Have a plausible storyline with motivated adversary, their tactics, a successful intrusion, lateral movement, and exfiltration. Plan for interesting forensic artifacts in each step that a security team can discover and pivot their investigation with. Involve systems that would complicate forensics. Target production. See what happens.

Choose organizational areas with weak security and involve their leadership in planning the exercise. Making them a part of the experience will be useful. For instance, If you’re having trouble with corporate endpoint security, design an exercise around spear phishing and malware that stretches those muscles (or lack thereof). However, don’t go so far that a team is simply decimated by the exercise and is forced to observe their uselessness up close.

Time and Preparation

These exercises took 1–2 months of preparation, and the windows the defenders expected a potential Red Team attack were 1–2 months long. For Red Team Three, we had 5 consultants from two firms for two weeks. We planned ahead for Post-Mortem resources, company all hands to describe lessons learned, etc.

Security Team Knowledge

The first exercise was an un-announced emotional system shock. It was a reality check and a pretty significant experience for several team members. The second was not, and announcing ahead of time for the third and fourth exercise became a major hype tool and inspired internal motivation from the team to win.

Red Teams need to be planned in absolute secrecy. The responding team cannot know a thing about what’s going on to be effective. No spoilers!

Involving senior leadership to bless the exercise pans is also a great way to involve them for remediation and post mortem functions. It will be less about getting them on the hook for helping, but getting them interested in the crazy stuff you’re about to pull.

Follow Up

Never let a good crisis go to waste. Because it’s not a real incident, extensive and calm note taking can take place without pressure. This helps set an example for future incidents which will have a very different form of urgency. The lessons from Security Breach 101 can be followed very closely.

Things to measure

Make sure team members that are panicking are comforted. Security incidents make people feel like their careers are in jeopardy, especially if they were hired to prevent the same intrusion they have to respond to. If you’re not emotionally in tune with this, do not do a Red Team exercise. If someone is panicking, tell them it’s a Red Team if it’s not entirely clear.

The time lag between each response milestone are important. How quickly was a system imaged and distributed to investigators? How fast was an IOC turned around to a firewall rule? How quickly could you clear employees as non-compromised?

Understand which team members were able to run down important resources in other organizations because of their tight personal networks with other employees. Discover any bad blood between two organizations. Find the boundary spanners on your team and make sure they are appreciated for repairing any bonds.

Watch for Legal, PR, Sales, etc working without full information or approval. You can’t let a salesperson tell you “I wanted my customer to hear about the breach from me first!” when they somehow hear about something. See more about this in Security Breach 101.

Shame

Don’t fuck this up because you shamed employees or teams with bad security awareness. Seriously, don’t. They’ll never come back and will never involve you or your team again.

Future

Security prevention should be unit test-able like any other technology. With the status quo — unit testing of security is a very manual process or only vulnerability assessment focused. I’m advising a company called AttackIQ — they’re working to automate Red Team lessons and hold defensive technology accountable when not actually working, much like a Red Team would. For instance, it really shouldn't take an enormous Red Team exercise to know if you’re highly responsive to an incident or if a malware appliance, you know, actually catches malware. Same with firewalls, ids, multifactor, etc.

Conclusion

Immersive Red Teams are extremely high risk, high reward. They give Defenders something to fight on a regular basis, improve morale, and weaponize security at a company to match up with reality.

They’re really fun to plan, too.

@magoo

I’m a security guy, former Facebook, Coinbase, and currently an advisor and consultant for a handful of startups. Incident Response and security team building is generally my thing, but I’m mostly all over the place.

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