Secure AI-Assisted Spec & Automation Training (June 2026 edition v3.0) is a production-oriented
private multi-session workshop from Chokmah LLC for CISOs, security leaders, and security engineers who use AI to produce
threat models, compliance mappings, technical specs, and automation—and who need those outputs to be
defensible under review, not merely fast.
The curriculum treats the AI generation process itself as an attack surface: prompt injection, hallucination in high-stakes
artifacts, model supply-chain and sovereign risk, weak validation, and missing pre-mortem discipline.
Workshop facts
Provider: Chokmah LLC · Instructor: Dr. Daniyel Yaacov Bilar (dyb)
Materials policy: full prompt library and harnesses ship to participants—not as a free public kit
Goal: turn AI from a risky shortcut into a disciplined, auditable capability with human-on-the-loop controls.
Why This Matters in 2026
Generation risks
Prompt injection, hallucinated controls, and unvalidated mappings that look authoritative under deadline pressure.
Model supply chain
Explicit handling of sovereign and provenance risk when choosing or mixing models (including non-US-hosted options).
Pre-mortem discipline
Structured failure forecasting embedded into prompts, artifacts, and automation—not a slide at the end of a project.
Attestation & oversight
Human-on-the-loop controls, validation gates, and evidence patterns so AI-assisted work can stand review.
Program Outcomes
By the end of the workshop, participants can design, generate, validate, govern, and operationalize AI-assisted security artifacts while managing risks introduced by AI systems themselves.
1. Risk-aware prompting
Structured strategies for threat models, compliance, specs, and automation logic—with injection, hallucination, and supply-chain mitigations.
2. Pre-mortem leadership
Facilitate rigorous pre-mortems on AI/agentic systems and embed mitigation triggers into artifacts and process.
3. Sovereign model judgment
Evaluate model choice, provenance, and fallback posture; document assumptions that affect board and regulator trust.
4. Validation & attestation
Design practical validation, attestation, and human-on-the-loop controls for generated outputs and pipelines.
5. Compliance automation
Build and critique AI-assisted automated checks with logging, evidence, and failure handling suitable for real environments.
6. Executive communication
Translate AI security risk and control design into clear language for technical teams, executives, and boards.
Curriculum Modules
Module 1: Prompt Engineering & Hardening
~60 minutes · Labs + reflection
Risks of LLMs when generating security artifacts
Universal header and task-specific hardened prompts
Mitigating prompt injection, hallucination, supply-chain, and validation gaps
Side-by-side baseline vs hardened generation
Deliverables: comparison, improved prompt pattern, short reflection
Module 2: Threat Modeling with AI
~75 minutes · Structured critique lab
Generate a high-quality threat model with hardened prompts
Identify risks introduced by the generation process
Apply pre-mortem and output validation checklists
Iterate under human critique—not unattended “accept all”
Generate automated compliance check procedures with hardened prompts
Implement scriptable checks with evidence and failure handling
Add pre-mortem triggers, provenance, and attestation-oriented logging
Critique AI-generated automation for hallucinated controls and edge cases
Deliverables: procedure, working check pattern, enhanced governance hooks, reflection
Capstone & Assessment
Integrated across the workshop
Apply the full stack to a chosen scenario under lightweight rubrics
Self-assessment plus targeted human review
Capstone presentation of risks, controls, and residual judgment
Focus: integrated risk judgment under uncertainty—not tool demos alone
Full prompt library, secure automation harnesses, labs, and assessments are provided to workshop participants—not published as a free public kit.
Sample Teaser: Universal Header Constraints
Every generation path in the workshop starts from a hardened universal header. Excerpt of the constraint pattern (illustrative—not the full delivery library):
# Illustrative excerpt — workshop materials include the full libraryMANDATORY CONSTRAINTS — apply to every high-stakes security generation:
• Surface risks of the AI generation process itself
(prompt injection, hallucination, model supply chain, validation bypass)
• For non-US / third-country models: explicit sovereign,
data-provenance, and supply-chain callouts
• Every attack path or control includes a pre-mortem trigger
and a concrete validation / attestation step
• Flag claims that need primary-source confirmation or human review
• Prefer structured output with strict schemas where possible
Participants also receive task prompts (threat model, compliance, spec, implement, automated checks) and secure PowerShell harness patterns for controlled runs.
Workshop Scenarios
Labs and samples span realistic operational domains:
BESS / energy storage
Threat modeling and control reasoning for battery energy storage and related cyber-physical constraints.
Defense ISR swarm
Governance and attestation pressure where autonomy, latency, and exception-handling collide.
SOC automation
AI-assisted detection and response automation with logging, failure modes, and human oversight.
Teams responsible for threat modeling, compliance automation, or AI governance
Organizations evaluating or already using AI tools (Claude, Kimi, and others) for security work—and needing model-risk discipline
Delivery
Private workshop (team or closed cohort)
Live facilitation with hands-on labs
Schedule and scope arranged per engagement
What you leave with
Hardened prompt patterns and critique habits
Pre-mortem and attestation design practice
Automation check patterns with governance hooks
Scenario-grounded artifacts from the labs
Frequently asked questions
What is Secure AI-Assisted Spec & Automation Training?
Chokmah LLC’s June 2026 edition v3.0 private multi-session workshop for CISOs and security leaders who generate high-stakes security artifacts with AI and need defensible process controls.
How long are the core modules?
About 5 hours 15 minutes of core labs (Modules 1–4), plus capstone. Schedule is arranged per engagement.
Who teaches the workshop?
Dr. Daniyel Yaacov Bilar (dyb), Principal & Subject Matter Expert, Chokmah LLC.
Is the full prompt library public?
No. Full library, harnesses, labs, and assessments are participant materials only.
Inquire about a private workshop
Discuss fit, team size, scenario focus, and delivery window for the June 2026 Secure AI-Assisted Spec & Automation program.