5 Cyber + AI Trends Smart CISOs Are Watching Now

Skeet Spillane
Dec 11
2 min read

Updated: 5 days ago

2026 isn’t waiting.

Between AI adoption, increasing cyber insurance pressures, and attackers getting smarter the risk landscape is already shifting.

Most teams will start thinking about this in January.

The ones who are ahead? They’re already paying attention to what matters.

Here are 5 cybersecurity and AI trends worth watching as you close out the year, because these are the conversations you’ll be having by Q1 whether you’re ready or not.

1. AI Is the New Insider Threat

Prediction: Shadow AI use by employees becomes the #1 blind spot.
What to Watch: Unsanctioned tools showing up in workflows, prompt-sharing risks, and no clear policy for what’s “safe” to use.
Why It Matters: The tools are already in use, but most orgs have no visibility, no inventory, and no boundaries. That's insider risk without malicious intent, but with real impact.

2. Detection Without AI Context Is Blind

Prediction: Traditional detection tools miss what matters when AI tools are in play.
What to Watch: Prompts, responses, and how LLMs are interacting with your data or apps.
Why It Matters: If your SOC can’t see what’s being prompted or how models respond, you’re operating blind. AI security requires context-aware detection, not just traditional alerts.

3. AI-Powered Phishing Gets Personal

Prediction: Voice, video, and written phishing attacks start mimicking real executive patterns.
What to Watch: Deepfake audio and video, spoofed writing styles, AI-generated “urgency” emails.
Why It Matters: These attacks won’t just look real. They’ll sound and feel familiar. User awareness training must evolve and executive teams must be directly prepared.

4. Your AI Stack Is a Supply Chain Risk

Prediction: AI plug-ins, APIs, and models inside vendor tools become weak links.
What to Watch: Opaque third-party models, unverified LLM integrations, and tools that update silently.
Why It Matters: If you don’t know what your vendors are running, and how those AI components work. You’re taking on silent risk.
Baseline Move: Your AI governance framework should require a documented inventory and Security review for every AI component in your environment.

5. Insurance Audits Start Asking AI Questions

Prediction: Underwriters get stricter and exclusions widen.
What to Watch: AI-related language in your cyber policy, controls around prompt use, and third-party AI exposure.
Why It Matters:
We don’t yet have a confirmed headline‑making example, and that’s exactly the point.
The opaque nature of AI vendors and the lack of audit trails create a scenario where insurers can (and increasingly will) deny claims. The silence around these events is a warning in itself.