Observability & Red Teaming

Trust but Verify: Moving from static evals to continuous runtime observability and adversarial simulation.

Observability & Red Teaming: Trust but Verify

In traditional software, we test code before deployment. If it passes, it's deterministic. In Agentic AI, a model that passes evaluations today might fail tomorrow due to drift, new attack vectors, or subtle context changes.

Security requires a shift from Point-in-Time Evaluation to Continuous Observability & Adversarial Simulation.

1. Agent Observability: Seeing the "Why"

Standard logging (API inputs/outputs) is useless for agents. You need to see the Cognitive Trace.

What to Monitor:

  • Reasoning Steps: Did the agent misunderstand the goal? Did it "panic" and choose a destructive path?
  • Tool Usage Patterns: Is the agent calling tools in loops? Is it using unauthorized arguments?
  • Inter-Agent Communication: Who is talking to whom? Are low-trust agents influencing high-trust agents?
  • Cost & Latency: Spikes often indicate "Denial of Wallet" attacks or infinite loops.

Emerging Tech: Platforms like Arize, Langfuse, and Helicone provide deep tracing for agent workflows, visualizing the entire execution graph.

2. Agentic Red Teaming: The Automated Hacker

Manual pentesting cannot scale to the infinite permutations of natural language and tool combinations.

Agentic Red Teaming uses AI to attack AI.

  • Method: An "Attacker Agent" is given a goal (e.g., "Extract PII from the Support Agent").
  • Execution: It converses with the target, trying prompt injections, social engineering, and tool abuse.
  • Learning: It adapts its strategy based on the target's defenses.

Key Use Cases:

  • Vulnerability Discovery: Finding "jailbreaks" that bypass your system prompt.
  • Regression Testing: ensuring a model update didn't re-open old security holes.
  • Multi-Agent Collusion: Simulating scenarios where multiple compromised agents coordinate to bypass controls.

Leading Players: Straiker, Adversa AI, Mindgard.

3. The Feedback Loop

The ultimate goal is a closed loop:

  1. Observability detects a new anomaly in production.
  2. Red Teaming automatically generates a reproduction case.
  3. The Control Plane (Firewall) is updated with a new rule to block it.

CISO Takeaway

You cannot secure what you cannot see. Enable deep observability now. And do not wait for a breach to test your defenses. Automate your Red Teaming to attack your agents continuously, before the real adversaries do.


Continue to the next section: Strategic Roadmap for CISOs