Our reasoning for Outflank Security Tooling

TLDR: We open up our internal toolkit commercially to other red teams. This post explains why.

Is blue catching your offensive actions? Are you relying on public or even commercial tools, but are these flagged by AV and EDR? Hesitant on investing deeply in offensive research and development? We’ve been there. But several years ago, we made the switch and started heavily investing in research. Our custom toolset was born.

Today we open up our toolset to other red teams in a new service called Outflank Security Tooling, abbreviated OST. We are super(!) excited about this. We truly think this commercial model is a win-win and will help other red teams and subsequently many organisations worldwide. You can find all the details at the product page. But there is more to be explained about why we do this, which is better suited in a blog post.

In this post you will find our reasoning for this service, our take on red team evolution, the relation to that other OST abbreviation and a short Q&A.

Our inhouse offensive toolset opened up for others

OST is a toolset that any red teamer would want in his arsenal. Tools that we use in our own red teaming engagements. Tools that my awesome colleagues have and continue to spend significant time researching, developing and maintaining. Proven tools that get us results.

OST is not another C2 framework. It’s an addition. A collection of tools for all stages of a red teaming operation. The following is a selection of the current toolset:

  • Office Intrusion Pack: abuse non-well-known tricks in Office to get that initial foothold.
  • Payload Generator: centralised and structured way to generate different kinds of payloads. No more heavy programming knowledge required to get payloads with awesome anti-forensics, EDR-evasion, guard-rails, transformation options, etc.
  • Lateral Pack: move lateral while staying under the radar of EDRs. A powerful collection of different ways for lateral movement.
  • Stage1 C2: OPSEC focussed C2 framework for stage 1 operations.
  • Hidden Desktop: operate interactive fat-client applications without the user experiencing anything. It’s pure interactive desktop magic.

Overall principles in a changing toolset

The toolset will change over time as we continue our R&D and as we adapt to the changing demand. But the following overall principles will stay the same:

  1. Awesome functionality that a red team would want.
  2. OPSEC safe operations that help you stay undetected.
  3. Easy to use for different skill levels within your team.
  4. Supporting documentation on concepts and details so you know what you are using.

You can find all details at the product page here. Now let’s get into our reasoning.

Public tools for red teams will not cut it anymore

Looking at our industry we have seen a strong rise in strength of blue teams the last couple of years. Both in tools and skills. This means far more effective detection and response. This is a good thing. This is what we wanted!

But this also means that public tools for red teams are becoming less and less effective against a more advanced blue team. For example, PowerShell used to be an easy choice. But nowadays any mature blue team is more than capable of stopping PowerShell based attacks. So red moves their arsenal to .NET. But proper EDRs and AMSI integration are among us. So .NET is not ideal anymore. It’s a matter of time before these attacks follow the same path as PowerShell. This pushes red into the land of direct system calls and low-level programming. But the battle has started in this area as well.

This is a good thing as it also pushes the real attackers to new territory. Hopefully shredding another layer of cybercriminals along the way.

In other words: to stay relevant, red teams need to invest heavily in their arsenal and skills.

This means more in-depth research for red teams

Doing in-depth R&D is not for the faint of hearts. It requires a distinct combination of knowledge and skills. Not only the level of detailed knowledge becomes a challenge. The broadness of knowledge as well. For example: a red team can have in-depth knowledge on low level lateral windows protocols. But without knowledge on getting your initial foothold, you miss a piece of the puzzle required for a complete operation.

It is becoming harder to have all required R&D skills in your red team. And we believe that is totally OK.

Novel R&D is not the role of a red team per se

At its core, doing novel R&D is not per se the role of the red team. Sure, it might help. But the end goal of red teams is helping their clients becoming more secure. They do this making an impact to their client via a realistic cyber-attack, and subsequently advising on how to improve. Super l33t R&D can help. But it is a means to a goal.

Take the following somewhat extreme examples:

  1. Red team A has not got the ability to do novel research and tool development. But it does have the ability to understand and use tools from others in their ops very effectively.
  2. Red team B does great detailed research and has the best custom tools. They built everything themselves. But they fail to execute this in a meaningful manner for their clients.

Red team B fails to help its client. Red team A is by far the more successful and effective red team.

This is not a new thing. We see it throughout our industry. Does a starting red team develop its own C2? No, it buys one of the available options. Even we – a pretty mature red team – still buy Cobalt Strike. Because it helps us to be more effective in our work.

This got us thinking. And eventually made us decide to start our OST service.

We founded Outflank to do red teaming right

Back in 2016, we founded Outflank because we wanted to:

  1. Help organizations battling the rising risk of targeted cyber-attacks.
  2. Push the industry with research.
  3. Have some fun along the way.

Starting with just 4 people, we were a highly specialized and high performing team. Not much has changed since then. Only the number has increased to 7. We don’t hire to grow as an objective. We grow when we find the right person on skill and personal level. It is the way we like our company to operate.

This has many benefits. Not at least a client base full of awesome companies that we are truly honoured to serve. And as we help them progress with their security, we are having fun along the way. This is what I call a win-win situation.

OST helps with heavy R&D economics

Our Outflank model does not scale well. We can’t serve every company on the planet and make it more secure. But in a way, we do want to help every company in the world. Or at least as many as we can. If we can’t serve them all, maybe we can at least have our tools serve them indirectly. Why not share these tools and in a way have them help companies worldwide?

This new model also helps with the economics of heavy R&D. As discussed earlier, modern red teaming requires tremendous research and development time. That is OK. We love doing that. But there comes a point that huge development time isn’t commercially feasible for our own engagements anymore. With OST, we have a financial incentive for heavy research which in turn helps the world to become more secure.

Or to put it boldly: OST enables us to finally take up major research areas that we were holding off due to too heavy R&D time. This then flows into the OST toolset, allowing customers and their clients to benefit.

We love sharing our novel tools and research

Our final reason is that we are techies at heart that love sharing our research on conferences, blogs and GitHub. We have done so a lot, especially if you look at the size of our little company. We would be very sad if we have to stop doing this.

But when you find your own previously shared research and tools in breach investigation reports on cyber criminals and state actors, it makes you think (example 1, example 2, example 3).

This brings me to that other OST abbreviation.

We are not blind to the public OST debate

OST is also an abbreviation for Offensive Security Tooling. You know, that heated discussion (especially on Twitter) between vocal voices on both blue and red side. A discussion where we perhaps have forgotten we are in this together. Red and blue share the same goal!

All drama aside, there is truth in the debate. Here at Outflank we highlighted the following arguments that we simply can’t ignore:

  1. Publicly available offensive tools are used in big cyber-attacks.
  2. Researchers sharing their offensive tools make other red teams (and blue teams) more effective. This in turn makes sure the defensive industry goes forward.
  3. The sharing of new research and tools is a major part of our industry’s ability to self-educate. This helps both red and blue.

The Outflank Security Tooling service contains tools built upon our research that we did not share before. We haven’t shared this because some of this research resulted in mayhem-level like tools. We don’t want these in the hands of cyber criminals and state actors. This decision was made well before the OST debate even started.

We counter the first and second arguments by not releasing our very powerful tools to the wide public, but to interested red teams.

We counter the third argument by continuing to present our research at conferences and share some PoCs of our non-mayhem-level tools. This way we can still contribute to the educational aspect that makes our industry so cool.

With our OST service we believe we make a (modest) step to a more secure world.

We are excited about OST and hope you are as well

We think OST is awesome! We believe it will allow other red teams to keep being awesome and help their clients. At the same time, OST provides an economic incentive to keep pushing for new research and tools that our customers will benefit from.

While we continue to release some of our non-dangerous research and PoCs to the public, OST allows us to share the dangerous tools only to selected customers. And have some fun while doing this. Again, a win-win situation.

We are excited about bringing OST to market. We hope you are as well!

This is not the end of the story

Instead, this is the start of an adventure. An adventure during which we already learned an awful lot about things such as the ‘Intrusion Software’ part of the Wassenaar Agreement, export controls and how to embed this technically into a service.

We believe that sharing information will make the world a better place. So, we will make sure to share our lessons learned during this adventure in future blog posts and at conferences. Such that our industry can benefit from this.


Does this mean you will stop publishing tools on your GitHub page?

No, sharing is at our core!

We will continue releasing proof-of-concept code and research on our GitHub page. We will keep contributing to other public offensive tools. Only our most dangerous tools will be released in a controlled manner via the OST service. Non-directly offensive tools such as RedELK will remain open source.

You can expect new public tool releases in the future.

Is OST available for everyone?

Due to the sensitivity of the tools, our ethical standards and because of export controls on intrusion software, we will be selective in which red teams we can serve with OST.

It is our obligation to prevent abuse of these tools in cybercriminal or geopolitical attacks. This will limit our clientele for sure. But so be it. We need clients that we can trust (and we take some technical measures against tool leakage of course).

Can I make my low skill pentest team be a l33t red team with OST?

Not really, and this is not the goal of OST. A toolset is an important part of a red teaming operation. But a team of skilled operators is at least as important!

We want red teams to understand what is happening under the hood when our tools are used. And OST supports them in this, for example by in-depth documentation of the techniques implemented in our tools.

Can I get a demonstration of the OST toolkit?