Ransomware groups are increasingly inserting AI bots into the negotiation loop to triage victims, collect leverage and scale their operations.
At Fortra, I have observed a growing trend of attackers deploying chatbots for first contact, with humans stepping in only after certain thresholds are met. This approach allows criminal organizations to manage multiple simultaneous negotiations efficiently while reserving human effort for the most profitable cases.
AI enables attackers to bridge language barriers, present more polished and sophisticated communications and, in some instances, obscure attribution signals by varying style and metadata, making it harder for defenders to trace activity to a single actor.
Defenders now face faster attack tempos due to agentic AI that can chain tasks and compress the timeline from intrusion to ransom demand. And AI-assisted ransomware campaigns can narrow the window from initial compromise to extortion from weeks to days, sometimes even hours. This acceleration forces incident response teams to make high-stakes decisions under extreme time and psychological pressures.
Practical identification
Determining whether you are communicating with an AI-driven negotiator, a human or a hybrid system is critical, as each requires a different approach. Indicators often emerge through linguistic and behavioral analysis. Uniformly polite and perfectly structured messages that arrive instantly at any hour suggest automation. Consistent mirroring of sentence structures and keyword reuse can also indicate a language model rather than a human operator. A sudden shift in tone or complexity after a pricing threshold often reveals a handoff from bot to human.
Defenders can probe these boundaries with low-risk behavioral tests. Ask a localized question, such as, “It is 5 p.m. in Denver, confirm your time.” Confusion or avoidance indicates automation. Offer oddly precise counters like “17.3% reduction” to test adaptability. Bots tend to normalize numbers or ignore nuanced phrasing. Repeating similar requests at timed intervals can potentially expose automated escalation sequences that respond at fixed rhythms.
Automation can also create predictable patterns. If messages reference policy or committee precisely at round percentages, or if countdowns advance mechanically without variation, you are likely dealing with an AI system rather than a distracted human.
Maintaining humans in the loop
Attackers exploit fear, fatigue and deadline pressure to force payment before victims can assess options. AI can help defenders by stabilizing emotional reactions, suggesting multiple tactical responses, and analyzing negotiation data. However, predictable machine phrasing can become a liability if attackers learn its patterns. The goal is not to automate negotiation entirely but to merge AI analytics with human unpredictability and judgment.
AI experts should still maintain human oversight at every stage. Automation should assist by generating and analyzing drafts, but only authorized human personnel should send communications. Require legal review and logging of every outbound message. These measures ensure that automated systems do not inadvertently reveal sensitive information or commit the organization to unintended actions.
Strategic response
Organizations should establish a written position that aligns with federal guidance: Do not pay ransom as a default stance. Define narrow business exceptions and pre-identify who has authority to approve them. Build a hybrid workflow in which AI assists by drafting and analyzing, but have a human lead, legal counsel and executive sponsor approve all responses.
Communication should focus on verification and stabilization rather than concession. Request proof that decryption keys exist and ask for sample decrypts of low-value files. Avoid implying willingness to pay. Use neutral business constraints, not legal or insurance details, to justify pauses. If automation is present, it will react uniformly to delay tactics, providing useful confirmation.
During price discovery, offer non-round numbers and staged counters tied to verifiable milestones such as decryption samples or deletion attestations. Watch for tone changes after specific thresholds, as this often indicates a switch from bot to human control. When that is detected, deliberately slow the tempo to regain negotiation leverage.
Hybrid negotiation operations in response to AI ransomware attacks should follow a structured approach. AI generates several candidate messages labeled cooperative, skeptical and firm. A human selects and edits one version, and legal performs a compliance review. Each interaction should be logged to monitor response time, tone shifts and escalation patterns. I recommend maintaining a phrasing library of paraphrased responses to reduce predictability and running tabletop exercises to red-team the negotiation process. Metrics such as price movement per round or escalation frequency can reveal patterns that adversaries may exploit.
Decision checkpoints for executives
Protecting human life and public safety takes priority over financial considerations. If encrypted systems affect patient care, critical infrastructure or safety services, escalate immediately. Always attempt to verify that decryption capabilities exist before considering any payment. If attackers cannot provide verifiable samples or hashes, the focus should likely remain on restoration from backups. Remember that if data has been exfiltrated, paying the ransom may not prevent future leaks or secondary extortion attempts. Federal agencies consistently emphasize this uncertainty.
Quick reference: Signs of an AI-driven negotiator
-
Replies arrive instantly and remain consistent at all hours.
-
The counterpart avoids specifics and repeats policy statements verbatim.
-
Sentence structure and uncommon word choices mirror your own.
-
The responder ignores benign questions about local time or logistics.
-
Pressure escalates on a fixed schedule that never drifts.
-
Writing style shifts abruptly once money thresholds are crossed, indicating human takeover.
Looking ahead
The negotiation landscape is evolving. Attackers are using AI for scalability, while human operators focus on complex or high-value victims. Defenders must mirror this structure intelligently by combining automation with disciplined human judgment. Teams balancing these elements will achieve faster stabilization and fewer decision errors under stress. The objective is not speed but precision, control and accountability. Those who pair AI efficiency with human insight will be best positioned to withstand and recover from the newest generation of ransomware extortion.
Get more commentary and insights focused on AI, cybersecurity, IT leadership and the latest trending topics three times a week with the InformationWeek newsletter.
