When we debuted OST back in 2021, we wrote a blog detailing both the product features and the rationale for investing time into this toolset. In 2022, we joined forces with Fortra and we can hardly believe it’s been over a year already. It was a big decision to go from being a small team of red teamers to becoming part of a large company, but we’re very pleased with the switch. In this reflection on the past 12 months, we want to provide an update on our mission, detail our continued dedication to OST, discuss the process of growing the Outflank community, and touch on where we’re headed next.  

Read more: Reflecting on a Year with Fortra and Next Steps for Outflank

A Product Oriented Focus

One of our biggest challenges when we joined Fortra was the decision to put most of our energy into Outflank Security Tooling (OST). Everyone on the team is a dedicated security consultant with years of experience in conducting complex red team engagements, so shifting much of our focus to a product was unfamiliar territory. While there was some initial discomfort, the adjustment was well worth it. We have enjoyed being able to spend much more time on research and development and to be able to create novel new tools that had real value.

A big reason this transition has been so successful is the additional resources and support provided by Fortra, a company that has a strong foothold in the cybersecurity space and is familiar with its challenges, like export controls and quality control. Fortra is particularly well versed in offensive cybersecurity, with multiple solutions that focus on pinpointing risks. With their acquisition of Cobalt Strike, they have already proved that they know how to successfully manage and foster the continued growth of advanced red teaming tools with unique R&D needs.

We have also greatly benefited from having access to extensive knowledge from colleagues in supporting areas like sales, customer support, legal, and marketing. Knowing we can confidently hand off tasks to these experienced teams has allowed us to go full throttle on the technology, of which we remain fully in charge. Additionally, we’ve been able to take advantage of the other R&D teams. This is particularly true with Cobalt Strike’s experts, which we’ll go into more detail on later on.

A Fruitful Year: New OST Tools Released

Our increased focus on OST is evident by the steady expansion of the toolset. In the past year alone, we’ve added the following new tools and capabilities:

• Stage1 v.2: A major overhaul of our C2 framework. It now supports BOFs, Socks proxying, C2 via HTTPS, SMB, raw TCP and files, and many more other features, while keeping the extreme OPSEC focus alive.
• Cobalt Strike Integrations: An easy way for operators to make use of custom UDRLs and custom Sleep Masks straight onto their Cobalt Strike payloads.
• New EDR Evasion: Super effective techniques embedded in tools such as Payload Generator and Stage1 implant generator. This includes DRIP allocations, ROP gadgets, and stealthy loading techniques.
• Hidden Desktop v2: A significant rewrite of Hidden Desktop in BOF format that is stealthier, faster in operation and easier in deployment.
• KernelTool and KernelKatz: Uses the power of vulnerable kernel drivers to directly interact with the Windows kernel to scrape credentials and/or modify other processes while EDRs let you through.
• EvilClicky: An easy way to abuse ClickOnce functionality.
• KerberosAsk: Updated to enhance Rubeus-like Kerberos trickery, in an OPSEC safe and in BOF format.

Expanding the OST Community

This increase in development has progressed us from crawling to walking, but growth in other areas has really made us feel like we’re now keeping a steady running pace.

While we’re working hard on new tool additions, we’ve also run multiple knowledge sharing sessions for OST users, covering topics like EDR evasion, Windows Kernel drivers, ClickOnce technique and Stage 1 C2 automation. We have been able to onboard many more red teams. Coupled with the fact that the Outflank team is more available on the Slack community and more red teams are coming to discuss ideas, the OST community is in a way better position that it ever was.

Not Forgetting What Makes Us Outflank

We’ve continued to conduct some trainings and red team engagements this last year, as this remains a core function of Outflank. Not only is it something we’re all passionate about, but it also helps in our development of OST. A critical part of R&D is to stay current on what red teamers are seeing in the wild. Running engagements keep our skills sharp and allow us to keep a pulse on the needs of other red teamers.  

An Expanding Team of Experts

One of the key factors in choosing to become part of Fortra was the opportunity to work with the Cobalt Strike team. We have used this benchmark product since the inception of Outflank and have designed OST to work both in tandem and together with Cobalt Strike (although OST certainly can be used independent of Cobalt Strike). Becoming coworkers with this welcoming, intelligent team has been as valuable as we hoped it would be. Both products have benefited from having added perspectives and the success of our collaborative efforts are already evident, with new integrations like our custom User Defined Reflective Loaders, custom Sleep Masks and YARA based payload analyses. While our products will remain independent, it’s clear that there are countless possibilities for innovation and alignment that we’re excited to continue to explore.

The Outflank team has also grown. As a small team that relies on effective communication and joint efforts, we carefully considered the potential outcomes of adding new members. We wanted to ensure they were a good fit and that we were adding expertise that would help OST continue to excel. With this in mind, we recently welcomed Tycho Nijon, our first full stack developer who is focusing on broader application development and Kyle Avery, a principal offensive specialist lead who is more focused on specialized research and development.  

The Ongoing Evolution of OST

Perhaps the biggest takeaway from this past year has been the overwhelmingly positive response from the market. Simply put, many red teams do not have the desire or resources to develop their own tools. At the same time, EDR tools are rapidly becoming more powerful, requiring red teams to double down on their OPSEC. OST fills that gap. Ultimately, we found that modern red teams really require support from beginning to end, from initial access to actions on objectives, from tooling to knowledge. With Outflank being part of Fortra, we are better equipped than ever to deliver solutions to meet these needs. Moving forward, OST customers can expect more Q&As, info sessions, and of course, new tools that expand and simplify red team capabilities.

If you’re interested in seeing all of the diverse offerings in OST, we recommend scheduling an expert led demo.