forbes.com
By Thomas Brewster, Forbes Staff.
Nov 15, 2025, 08:00am ESTUpdated Nov 16, 2025, 06:40am EST

The U.S. government has been contracting stealth startup Twenty, which is working on AI agents and automated hacking of foreign targets at massive scale.
The U.S. is quietly investing in AI agents for cyberwarfare, spending millions this year on a secretive startup that’s using AI for offensive cyberattacks on American enemies.
According to federal contracting records, a stealth, Arlington, Virginia-based startup called Twenty, or XX, signed a contract with the U.S. Cyber Command this summer worth up to $12.6 million. It scored a $240,000 research contract with the Navy, too. The company has received VC support from In-Q-Tel, the nonprofit venture capital organization founded by the CIA, as well as Caffeinated Capital and General Catalyst. Twenty couldn’t be reached for comment at the time of publication.

Twenty’s contracts are a rare case of an AI offensive cyber company with VC backing landing Cyber Command work; typically cyber contracts have gone to either small bespoke companies or to the old guard of defense contracting like Booz Allen Hamilton or L3Harris.

Though the firm hasn’t launched publicly yet, its website states its focus is “transforming workflows that once took weeks of manual effort into automated, continuous operations across hundreds of targets simultaneously.” Twenty claims it is “fundamentally reshaping how the U.S. and its allies engage in cyber conflict.”

Its job ads reveal more. In one, Twenty is seeking a director of offensive cyber research, who will develop “advanced offensive cyber capabilities including attack path frameworks… and AI-powered automation tools.” AI engineer job ads indicate Twenty will be deploying open source tools like CrewAI, which is used to manage multiple autonomous AI agents that collaborate. And an analyst role says the company will be working on “persona development.” Often, government cyberattacks use social engineering, relying on convincing fake online accounts to infiltrate enemy communities and networks. (Forbes has previously reported on police contractors who’ve created such avatars with AI.)

Twenty’s executive team, according to its website, is stacked with former military and intelligence agents. CEO and cofounder Joe Lin is a former U.S. Navy Reserve officer who was previously VP of product management at cyber giant Palo Alto Networks. He joined Palo Alto after the firm acquired Expanse, where he helped national security clients determine where their networks were vulnerable. CTO Leo Olson also worked on the national security team at Expanse and was a signals intelligence officer at the U.S. Army. VP of engineering Skyler Onken spent over a decade at U.S. Cyber Command and the U.S. Army. The startup’s head of government relations, Adam Howard, spent years on the Hill, most recently working on the National Security Council transition team for the incoming Trump administration.

The U.S. government isn’t the only country using AI to build out its hacking capabilities. Last week, AI giant Anthropic released some startling research: Chinese hackers were using its tools to carry out cyberattacks. The company said hackers had deployed Claude to spin up AI agents to do 90% of the work on scouting out targets and coming up with ideas on how to hack them.

It’s possible the U.S. could also be using OpenAI, Anthropic or Elon Musk’s xAI in offensive cyber operations. The Defense Department gave each company contracts worth up to $200 million for unspecified “frontier AI” projects. None have confirmed what they’re working on for the DOD.

Given its focus on simultaneous attacks on hundreds of targets, Twenty’s products appear to be a step up in terms of cyberwarfare automation.

By contrast, beltway contractor Two Six Technologies has received a number of contracts in the AI offensive cyber space, including one for $90 million in 2020, but its tools are mostly to assist humans rather than replace them. For the last six years, it’s been working on developing automated AI “to assist cyber battlespace” and “support development of cyber warfare strategies” under a project dubbed IKE. Reportedly its AI was allowed to press ahead with carrying out an attack if the chances of success were high. The contract value was ramped up to $190 million by 2024, but there’s no indication IKE uses agents to carry out operations at the scale that Twenty is claiming. Two Six did not respond to requests for comment.

AI is much more commonly used on the defensive side, particularly in enterprises. As Forbes reported earlier this week, an Israeli startup called Tenzai is tweaking AI models from OpenAI and Anthropic, among others, to try to find vulnerabilities in customer software, though its goal is red teaming, not hacking.

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