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Run direct, indirect, multi-turn, encoded, split-payload, and…

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Week 15: Project 3 Hardening Sprint (Agent & Workflow System) & Cross-Project Red Teaming Start

The five hours

  1. 01

    Concepts & system design

    60 min

    R04 — OWASP LLM01

    R05 — MITRE ATLAS

    R28 — Microsoft PyRIT scoring

    Read the assigned sections; map the mechanism, threat model and trade-offs.

  2. 02

    Project implementation

    120 min

    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.

    Build, integrate, debug and improve the increment in the active project.

  3. 03

    Security lab

    60 min

    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.

    Test the abuse case, failure path, authorization bypass or resource limit.

  4. 04

    Verification & evidence

    30 min

    Cross-project injection red-team report and updated D8 regression test cases.

    Add or run regression tests; record the 9-point evidence record.

  5. 05

    Deliberate practice & Socratic review

    30 min

    Answer 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.

  6. total5 h

Read today · inside the concepts block

R04 R05 R28

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 Project
    OWASP 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 Developer
    Episode 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 Swain
    Indirect 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 Learn
    2. 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
  • repoGitHub
    microsoft/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

0/9

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

empty

The two source formulations

verbatim · nothing summarised

Project & 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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