On February 28, OpenAI announced it had reached a deal that will allow the US military to use its technologies in classified settings. CEO Sam Altman said the negotiations, which the company began pursuing only after the Pentagon’s public reprimand of Anthropic, were “definitely rushed.”

In its announcements, OpenAI took great pains to say that it had not caved to allow the Pentagon to do whatever it wanted with its technology. The company published a blog post explaining that its agreement protected against use for autonomous weapons and mass domestic surveillance, and Altman said the company did not simply accept the same terms that Anthropic refused. 

You could read this to say that OpenAI won both the contract and the moral high ground, but reading between the lines and the legalese makes something else clear: Anthropic pursued a moral approach that won it many supporters but failed, while OpenAI pursued a pragmatic and legal approach that is ultimately softer on the Pentagon. 

It’s not yet clear if OpenAI can build in the safety precautions it promises as the military rushes out a politicized AI strategy during strikes on Iran, or if the deal will be seen as good enough by employees who wanted the company to take a harder line. Walking that tightrope will be tricky. (OpenAI did not immediately respond to requests for additional information about its agreement.)

But the devil is also in the details. The reason OpenAI was able to make a deal when Anthropic could not was less about boundaries, Altman said, but about approach. “Anthropic seemed more focused on specific prohibitions in the contract, rather than citing applicable laws, which we felt comfortable with,” he wrote. 

OpenAI says one basis for its willingness to work with the Pentagon is simply an assumption that the government won’t break the law. The company, which has shared a limited excerpt of its contract, cites a number of laws and policies related to autonomous weapons and surveillance. They are as specific as a 2023 directive from the Pentagon on autonomous weapons (which does not prohibit them but issues guidelines for their design and testing) and as broad as the Fourth Amendment, which has supported protections for Americans against mass surveillance. 

However, the published excerpt “does not give OpenAI an Anthropic-style, free-standing right to prohibit otherwise-lawful government use,” wrote Jessica Tillipman, associate dean for government procurement law studies at George Washington University’s law school. It simply states that the Pentagon can’t use OpenAI’s tech to break any of those laws and policies as they’re stated today.

The whole reason Anthropic earned so many supporters in its fight—including some of OpenAI’s own employees—is that they don’t believe these rules are good enough to prevent the creation of AI-enabled autonomous weapons or mass surveillance. And an assumption that federal agencies won’t break the law is little assurance to anyone who remembers that the surveillance practices exposed by Edward Snowden had been deemed legal by internal agencies and were ruled unlawful only after drawn-out battles (not to mention the many surveillance tactics allowed under current law that AI could expand). On this front, we’ve essentially ended up back where we started: allowing the Pentagon to use its AI for any lawful use. 

OpenAI could say, as its head of national security partnerships wrote yesterday, that if you believe the government won’t follow the law, then you should also not be confident it would honor the red lines that Anthropic was proposing. But that’s not an argument against setting them. Imperfect enforcement doesn’t make constraints meaningless, and contract terms still shape behavior, oversight, and political consequences.

OpenAI claims a second line of defense. The company says it maintains control over the safety rules governing its models and will not give the military a version of its AI stripped of those safety controls. “We can embed our red lines—no mass surveillance and no directing weapons systems without human involvement—directly into model behavior,” wrote Boaz Barak, an OpenAI employee Altman deputized to speak on the issue about X. 

But the company doesn’t specify how its safety rules for the military differ from its rules for normal users. Enforcement is also never perfect, and it is especially unlikely to be when OpenAI is rolling out these protections in a classified setting for the first time and is expected to do so in just six months.

There’s another question beneath all this: Should it be down to tech companies to prohibit things that are legal but that they find morally objectionable? The government certainly viewed Anthropic’s willingness to play this role as unacceptable. On Friday evening, eight hours before the US launched strikes in Tehran, Defense Secretary Pete Hegseth issued harsh remarks on X. “Anthropic delivered a master class in arrogance and betrayal,” he wrote, and echoed President Trump’s order for the government to cease working with the AI company after Anthropic sought to keep its model Claude from being used for autonomous weapons or mass domestic surveillance. “The Department of War must have full, unrestricted access to Anthropic’s models for every LAWFUL purpose,” Hegseth wrote.

But unless OpenAI’s full contract will reveal more, it’s hard not to see the company as sitting on an ideological seesaw, promising that it does have leverage it will proudly use to do what it sees as the right thing while deferring to the law as the main backstop for what the Pentagon can do with its tech.

There are three things to be watching here. One is whether this position will be good enough for OpenAI’s most critical employees. With AI companies spending so heavily on talent, it’s possible that some at OpenAI see in Altman’s justification an unforgivable compromise.

Second, there is the scorched-earth campaign that Hegseth has promised to wage against Anthropic. Going far beyond simply canceling the government’s contract with the company, he announced that it would be classified as a supply chain risk, and that “no contractor, supplier, or partner that does business with the United States military may conduct any commercial activity with Anthropic.” There is significant debate about whether this death blow is legally possible, and Anthropic has said it will sue if the threat is pursued. OpenAI has also come out against the move.

Lastly, how will the Pentagon swap out Claude—the only AI model it actively uses in classified operations, including some in Venezuela—while it escalates strikes against Iran? Hegseth granted the agency six months to do so, during which the military will phase in OpenAI’s models as well as those from Elon Musk’s xAI.

But Claude was reportedly used in the strikes on Iran hours after the ban was issued, suggesting that a phase-out will be anything but simple. Even if the months-long feud between Anthropic and the Pentagon is over (which I doubt it is), we are now seeing the Pentagon’s AI acceleration plan put pressure on companies to relinquish lines in the sand they had once drawn, with new tensions in the Middle East as the primary testing ground.

If you have information to share about how this is unfolding, reach out to me via Signal (username: jamesodonnell.22).