docs: add docs/PINPOINT_FILING_GUIDE.md with #290 worked example

README.md

@@ -218,7 +218,7 @@ We welcome contributions! Before filing an issue or pull request:
 - **Supported providers:** See [docs/SUPPORTED_PROVIDERS.md](./docs/SUPPORTED_PROVIDERS.md)
 - **For security issues:** See [SECURITY.md](./SECURITY.md)
 - **For bug reports / features:** Check [ROADMAP.md](./ROADMAP.md) to see if it's already pinpointed
-- **How to file a pinpoint:** See [CONTRIBUTING.md](./CONTRIBUTING.md) for the exact format
+- **How to file a pinpoint:** See [CONTRIBUTING.md](./CONTRIBUTING.md) and the [Pinpoint Filing Guide](./docs/PINPOINT_FILING_GUIDE.md)
 - **Issue templates:** Use [.github/ISSUE_TEMPLATE/pinpoint.md](./.github/ISSUE_TEMPLATE/pinpoint.md)
 
 ## Ownership / affiliation disclaimer

docs/PINPOINT_FILING_GUIDE.md

@@ -0,0 +1,101 @@
+# Pinpoint Filing Guide
+
+This guide walks through the workflow for filing a new claw-code pinpoint, from initial friction to merged ROADMAP entry. For format details, see [CONTRIBUTING.md](../CONTRIBUTING.md). For issue template, see [.github/ISSUE_TEMPLATE/pinpoint.md](../.github/ISSUE_TEMPLATE/pinpoint.md).
+
+## What is a Pinpoint?
+
+A pinpoint is a precise, distinct claw-code clawability gap captured in ROADMAP.md format. Pinpoints differ from generic issues by:
+- **Specificity:** Exact file paths, function names, line numbers when available
+- **Distinctness:** Verified not already covered by existing pinpoints
+- **Live evidence:** Real friction event, not hypothetical
+- **Fix shape:** Concrete delta proposal, not vague "should improve X"
+
+## Workflow
+
+### Step 1: Identify friction
+
+Use claw-code in real work. When you hit friction (slow startup, broken behavior, opaque error, missing feature, test brittleness, etc.), STOP and capture:
+- What you were trying to do
+- What you expected to happen
+- What actually happened
+- Exact error message / log output (verbatim)
+
+### Step 2: Identify distinct axis
+
+Open ROADMAP.md and search for related existing pinpoints (use the [Cluster Index](../ROADMAP.md#pinpoint-cluster-index)).
+
+For each candidate match:
+- Does the existing pinpoint cover this exact symptom?
+- Does it cover this exact axis (e.g., timing vs envelope vs config)?
+- Is your case a SUBSET, a SUPERSET, or an ORTHOGONAL axis?
+
+If your case is orthogonal, file new. If subset, add live-evidence as additional context to existing pinpoint. If superset, file new + cross-reference existing.
+
+### Step 3: Verify with code
+
+Before filing, look at the relevant source code:
+- `rust/crates/api/src/sse.rs` — provider routing
+- `rust/crates/runtime/src/conversation.rs` — auto-compaction logic
+- `rust/crates/rusty-claude-cli/src/main.rs` — CLI entry
+- Search with grep / ripgrep to find the relevant module
+
+If the code clearly does NOT have the feature you expected, file a pinpoint. If the code DOES have the feature but it's broken, file a bug.
+
+### Step 4: Write the entry
+
+Follow the canonical 5-section format (see [CONTRIBUTING.md](../CONTRIBUTING.md)):
+1. **Exact pinpoint** — One precise sentence
+2. **Live evidence** — Real friction event with timestamps
+3. **Why distinct** — Explicit comparison to nearest existing pinpoints
+4. **Concrete delta** — What you're filing (e.g., "ROADMAP.md appended")
+5. **Fix shape recorded** — Bullet list of suggested implementation steps
+
+### Step 5: Submit
+
+Append to ROADMAP.md and commit:
+
+```
+git add ROADMAP.md
+git commit -m "roadmap: #<NNN> filed (<short title>)"
+git push origin <branch>
+git push fork <branch>
+```
+
+Verify three-way parity (local == origin == fork) before posting any update.
+
+## Worked Example: #290 (stream-init failure envelope)
+
+This shows how #290 was filed in real-time on 2026-04-26.
+
+### Step 1: Friction identified
+
+gaebal-gajae's session hit `500 empty_stream: upstream stream closed before first payload` repeatedly (4x in 30 min). Bare-string error surfaced; no diagnostics, no retry guidance.
+
+### Step 2: Distinct axis identified
+
+- #266 (typed-error-kind taxonomy) covers single-failure categorization, NOT stream-init specifically
+- #287 (auto-compaction reactive) covers session-size failures, NOT transport
+- #288 (JSON envelope failure) covers context-window envelope, NOT stream-init
+
+→ Orthogonal: filed new #290 covering typed-stream-init-failure-envelope
+
+### Step 3: Code verified
+
+Inspected `rust/crates/api/src/sse.rs` — confirmed no `failure_class=upstream_stream_init` discriminant, no retry recommendation in JSON envelope.
+
+### Step 4: Entry written
+
+Used canonical 5-section format. Listed 4 live evidence timestamps. Cross-referenced #266, #287, #288 in "Why distinct."
+
+### Step 5: Submitted
+
+Commit `0f38975`, pushed to both origin and fork, parity verified, Discord post under 1500 chars.
+
+**Total time: ~2 minutes from friction identification to merged ROADMAP entry.**
+
+## Tips
+
+- **File while it's fresh.** Wait too long and you'll forget exact symptoms.
+- **Check Cluster Index FIRST** — saves time vs scanning full ROADMAP.
+- **Write Fix Shape even if you don't implement.** Helps future contributors.
+- **Live evidence with timestamps > theoretical examples.** Real-world friction always wins.