Skip to content
Roadmap0/111
not startedstudy day 4 of 6 · covers original day 12

Add tool timeouts

P1 AssistantS2M5D1
not started0/5 blocks
0/5
Jump & context

Week 2: Prompt Injection, Crescendo Fuzzing, Streaming, Persistence & Cost Controls

The five hours

  1. 01

    Concepts & system design

    60 min

    R01 — Async timeouts & exception handling

    R10 — OWASP Error Handling & Logging Cheat Sheets

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

  2. 02

    Project implementation

    120 min

    Add per-tool timeouts, bounded exponential-backoff retries, and safe error contracts to P1.

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

  3. 03

    Security lab

    60 min

    Run D1 injection cases combined with simulated tool timeouts and malformed tool outputs.

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

  4. 04

    Verification & evidence

    30 min

    Combined tool-security regression suite and residual-risk notes.

    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

R01 R10

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 Cheat Sheet Series
    Logging

    Specifies what belongs in a log event and what must never appear (credentials, tokens, sensitive payloads), which is the constraint your safe error contract has to satisfy while staying debuggable.

    R10checked 2026-11-11
  • videoArjanCodes · 24:02
    Retry Pattern: The Secret to Resilient Python Code

    Covers the retry decorator, backoff, and which exceptions are safe to retry, including the idempotency question that decides whether a failed tool call may be repeated at all.

    S7checked 2026-11-11
  • videoYash Jain · 16:14
    Retry LLM API Calls Automatically with Python Tenacity

    Applies bounded retries with exponential backoff to LLM provider calls, showing how to cap attempts so a slow model cannot turn into unbounded spend.

    R03M5checked 2026-11-11
  • articleAWS Architecture Blog
    Exponential Backoff and Jitter

    Gives the full-jitter formula and the measured reason plain exponential backoff still synchronizes clients into retry storms, which is the difference between bounded and unbounded retries.

    M5S7checked 2026-11-11
  • repoGitHub
    jd/tenacity

    Retrying library with stop, wait, and retry conditions you can compose into per-tool attempt and deadline budgets rather than one global retry policy.

    S7checked 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

P1 | `D1` (Crescendo Attack Fuzzer) | S2, M5

Core Implementation

Add per-tool timeouts, bounded exponential-backoff retries, and safe error contracts to P1.

Security Lab

Run D1 injection cases combined with simulated tool timeouts and malformed tool outputs.

Verification & Evidence

Combined tool-security regression suite and residual-risk notes.

Read Today (60m Concepts Block)

R01 (Async timeouts & exception handling), R10 (OWASP Error Handling & Logging Cheat Sheets).

---