Ransomware Negotiator Mails $340,000 in Cash to Attackers After Security Training Only Mentioned Gift Cards and Bitcoin

DALLAS, TX—Crisis management consultant Derek Hastings is facing intense scrutiny after paying a ransom via cash with "extreme professionalism."

After successfully resolving a ransomware attack against logistics firm TransportCore by mailing $340,000 in cash via Priority Overnight to an address in Romania, citing that his company's mandatory security awareness training had only warned about gift cards and cryptocurrency.

The incident began on Monday when TransportCore's systems were encrypted by the BlackDawn ransomware group, who demanded $340,000 within 72 hours. Hastings, a third-party incident response consultant with eight years of experience and current on all compliance training, immediately took charge of negotiations and payment logistics.

"The training module was very clear about not purchasing iTunes gift cards if someone calls claiming to be the IRS," Hastings explained in a press briefing Thursday. "There was also an entire section about Bitcoin being untraceable and used by criminals. But nobody said anything about regular mail. I went through the whole 45-minute course twice to be sure."

According to TransportCore's incident timeline, Hastings withdrew the cash from three separate bank branches, packed it into a reinforced shipping box with bubble wrap, and sent it via overnight shipping. The package included a handwritten note requesting a decryption key and Hastings's business card "for future reference."

The cash arrived 36 hours later. The ransomware group, apparently confused by the payment method, initially refused to provide the decryption key because they assumed it was a law enforcement sting operation. After Hastings sent them the tracking history as proof of legitimacy, BlackDawn provided a working key and posted a message to their dark web portal praising his "creativity and professionalism."

Security experts note that Hastings's approach technically complied with TransportCore's security training, which was developed by their third-party compliance vendor. The training's final quiz included questions about identifying phishing emails, recognizing gift card scams, and the dangers of cryptocurrency, but contained no specific guidance about physical currency or international shipping of large cash sums to active cybercriminals.

"This is technically a gap in our training content," admitted SecureAware product manager Michael Torres. "We'll be adding a section about cash in our Q3 content update, along with revised guidance about money orders, personal checks, and, I guess, wire transfers to be safe."

Authorities raided the address on Thursday but found only a 19-year-old university student who claimed he had agreed to receive a package for $200 from someone on Telegram. The cash had already been collected by an unknown individual.

TransportCore has since updated its security training to include a new section titled "Approved Payment Methods for Cyber Extortion (There Are None)."

Hastings remains employed as a consultant and has received three inquiries from other companies requesting his services, though all three specifically asked him not to mail anything to anyone under any circumstances.