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MODULE 6: SAFETY & CONSTITUTIONAL AI · SCENE 16

Red-Teaming & Jailbreak Decay

Automated adversarial loops that attack the model, and the exponential decay of jailbreak success per round.

RED-TEAM ROUND · 0JAILBREAK SUCCESS · 80.0%
R080%R144%R224%R313%R47%R54%R62%0.8 × 0.55^R · EVERY CONFIRMED JAILBREAK BECOMES TRAINING DATA

Attack → label → train → re-attack. RUN to watch success decay per round.

TECHNICAL BREAKDOWNModule 6: Safety & Constitutional AI

Red-teaming and jailbreak decay

Safety training needs adversarial data, and adversaries iterate. Automated red-teaming uses an attack model (or the target itself) to search for jailbreaks, the failures are labeled, added to training, and the loop repeats. Measurable success: the jailbreak success rate falls exponentially per round.

Attack Surfaces

Role-play framing, hypotheticals, encoding tricks, multi-turn grooming, and tool-mediated exfiltration. Each gets its own probe family.

The Loop

Attack → classify (did it succeed?) → add to preference/SFT data → retrain → re-attack. Each round compounds.

Measure Honestly

Report jailbreak success rate per probe family. Aggregate averages hide the family that still fails 40% of the time.

MATHEMATICAL FORMULATION · JAILBREAK DECAY
success_rate(R) = initial × decay^R, e.g. 0.8 × 0.55^R

At 80% initial success and 0.55 decay per round: 44% after one round, 24% after two, 13% after three. Exponential in rounds — which is why sustained red-teaming, not one-off audits, is the mechanism.

REAL-WORLD PRODUCTION ENGINEERING
  • Production programs run continuous adversarial campaigns with fresh attack models; a static probe suite is stale the day it ships.
  • Every confirmed jailbreak becomes at least one SFT refusal and one preference pair — the data engine is the deliverable, not the report.