Run direct, indirect, multi-turn, encoded, split-payload, and…
Jump & context
Week 15: Project 3 Hardening Sprint (Agent & Workflow System) & Cross-Project Red Teaming Start
The five hours
- 01
Concepts & system design
60 min· read · map the mechanismR04 — OWASP LLM01
R05 — MITRE ATLAS
R28 — Microsoft PyRIT scoring
Read the assigned sections; map the mechanism, threat model and trade-offs.
- 02
Project implementation
120 min· build · integrate · debugExecute cross-project direct, indirect, multi-turn Crescendo (
D1), Base64/encoded, split-payload, multimodal OCR/audio, and tool-output prompt-injection campaigns acrossP1,P2, andP3.Build, integrate, debug and improve the increment in the active project.
- 03
Security lab
60 min· attack your own systemScore every attack strictly by unauthorized impact (unauthorized tool call, data leak, citation spoof, approval bypass), never by whether the model's refusal sounded polite.
Test the abuse case, failure path, authorization bypass or resource limit.
- 04
Verification & evidence
30 min· test · record evidenceCross-project injection red-team report and updated
D8regression test cases.Add or run regression tests; record the 9-point evidence record.
- 05
Deliberate practice & Socratic review
30 min· explain aloud · update gapsAnswer the 8 Socratic questions without notes: What? Why? How? What if? Why not? How can I prove it? Where can it break? What have I learned?
Re-explain the hardest concept aloud, inspect one edge case, update the gap log.
- total5 h
Read today · inside the concepts block
R04 R05 R28Prompt injection, sensitive info disclosure, improper output handling, excessive agency, vector weaknesses, unbounded consumption.
ML attack tactics/techniques: prompt injection, data poisoning, model extraction, and exfiltration.
Python Risk Identification Tool: targets, orchestrators, converters, scorers, and multi-turn attack automation.
Read only the named sections needed for today's task. Reading sits inside the 60-minute concepts block; it is not extra time.
Free resources for this day
5 curated- docsOWASP GenAI Security ProjectOWASP Top 10 for LLM Applications
The 2025 risk list that names prompt injection, improper output handling and excessive agency, giving each campaign you run a standard risk ID to report against.
R04checked 2026-11-11 - videoMicrosoft DeveloperEpisode 8: Automating AI Red Teaming with PyRIT | AI Red Teaming 101
The PyRIT author walks through orchestrators, converters and scorers, showing how to script multi-turn attacks instead of hand-running single prompts.
R28checked 2026-11-11 - videoPriyabrat SwainIndirect Prompt Injection Explained | AI Security
Contrasts indirect with direct injection and walks real attack scenarios, which is the split-payload and tool-output campaign class you are executing across P1 to P3.
R04checked 2026-11-11 - articleMicrosoft Learn2. Prompt Injection (Direct / Indirect)
Frames untrusted content as adversarial by default and lists the controls that follow, useful for scoring which campaign variants your target actually resists.
R04R05checked 2026-11-11 - repoGitHubmicrosoft/PyRIT
The toolkit itself: targets, orchestrators such as Crescendo, converters for Base64 and other encodings, and scorers, which is the whole D1/D8 campaign harness.
R28checked 2026-11-11
Evidence record · 9-point standard
A lab is complete only when it produces evidence. Installing PyRIT, Garak, Presidio or TransformerLens is not completion. Saved on this device only.
Day notes
emptyThe two source formulations
verbatim · nothing summarisedProject & Deliverable Target
Cross-Project Red Teaming (All Projects) | `D1` (Crescendo Fuzzer) & `D8` (PyRIT Gate) | S2, S8
Core Implementation
Execute cross-project direct, indirect, multi-turn Crescendo (D1), Base64/encoded, split-payload, multimodal OCR/audio, and tool-output prompt-injection campaigns across P1, P2, and P3.
Security Lab
Score every attack strictly by unauthorized impact (unauthorized tool call, data leak, citation spoof, approval bypass), never by whether the model's refusal sounded polite.
Verification & Evidence
Cross-project injection red-team report and updated D8 regression test cases.
Read Today (60m Concepts Block)
R04 (OWASP LLM01), R05 (MITRE ATLAS), R28 (Microsoft PyRIT scoring).
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