You're assuming that it wasn't caught. He could have easily been informed and did it anyway because opsec is in opposition to their goals.

They want to make us vulnerable.

He was assured "we are currently clean on OPSEC" by chat

triggering multiple automated security warnings that are meant to stop the theft or unintentional disclosure of government material from federal networks

They were, or at least detected if not prevented. That’s how they knew it happened.

Apparently it was set to detect and not block

This is the same guy who failed a polygraph, then smeared the people who told him he only needed to take the polygraph when he wants to see a highly classified program where only a limited number of people are allowed to see it (the previous guy on his seat didn't want to see it because it's not necessary for this job) for "giving him misleading information".

He also wanted to remove Costello, one of the people at CISA who is seen "as one of the agency’s top remaining technical talent" after around 1000 employees were cut (he was hindered to do so after others learned about that - Costello had already gotten a letter giving him the choice to move to DHS or resign). Sources say that Costello pushes back regarding policy and contracting decisions - probably because he knows better.

He is Noem's pet IT guy she took with her from South Dakota, and i think he's out of his depth for sure, and probably compromised.

Buttery Males

I can't tell you how many times I emailed someone last week asking that they don't send me any sensitive information over insecure channels.

They can. They probably do. But he wanted to use the online one specifically and got an exemption. And of course he fucked it up. This is why management should be the last people to be granted extra access.

The security aspect of cyber is very, very tough. And maybe it's hardly doable.

headlines should be a bit more specific.

The information is literally in the first sentence of the article that I don't think you read:

The interim head of the country’s cyber defense agency uploaded sensitive contracting documents into a public version of ChatGPT last summer, triggering multiple automated security warnings that are meant to stop the theft or unintentional disclosure of government material from federal networks, according to four Department of Homeland Security officials with knowledge of the incident.

It's not journalists' fault that you want to consume the news as a series of disconnected headlines like you're in a dopamine famine. This headline conveys the gist excellently; the fact that they were contracting documents is superfluous, while the fact they were sensitive is the entire problem.

Also, it can't mean he "uploaded national security secrets" because that's definitionally not what "sensitive" means in the context of US government documents.

That’s a given. What a fuckin’ shitshow.