I'm curious to hear your take on the situation in the article.

Based on your experience, do you think there are specific ways the author could have communicated differently to elicit a better response from the lawyers?

It would take a bit of time to re-read the entire chain and come up with highly specific ways. The way I read the exchange, the lawyer basically wants the programmer to shut up and not disclose the vulnerability, and is using threatening legal language. While the programmer sees themself as a responsible person doing the company a favor in a principled way.

Some things I can see. I think the way the programmer worded this sounds adversarial; I wouldn't have written it that way, but ultimately, there is nothing wrong with it: "I am offering a window of 30 days from today the 28th of April 2025 for [the organization] to mitigate or resolve the vulnerability before I consider any public disclosure."

When the lawyer sent the NDA with extra steps: the programmer could have chosen to hire a lawyer at this point to get advice. Or they could ignore this entirely (with the risk that the lawyer may sue him?), or proceed to negotiate terms, which the programmer did (offering a different document to sign).

IIUC, at that point, the lawyer went away and it's likely they will never contact this guy again, unless he discloses their name publicly and trashes their security, at which point the lawyer might sue for defamation, etc.

Anyway, my take is that as soon as the programmer got a lawyer email reply (instead of the "CTO thanking him for responsible disclosure"), he should have talked to his own lawyer for advice. When I have situations similar to this, I use the lawyer as a sounding board. i ask questions like "What is the lawyer trying to get me to do here?" and "Why are they threatening me instead of thanking me", and "What would happen if I respond in this way".

Depending on what I learned from my lawyer I can take a number actions. For example, completely ignoring the company lawyer might be a good course of action. The company doesn't want to bring somebody to court then have everybody read in a newspaper that the company had shitty security. Or writing a carefully written threatening letter- "if you sue me, I'll countersue, and in discovery, you will look bad and lose". Or- and this is one of my favorite tricks, rewriting the document to what I wanted, signing that, sending it back to them. Again, for all of those, I'd talk to a lawyer and listen to their perspective carefully.