Headroom Learn¶

Offline failure learning for coding agents. Analyzes past conversations, finds what went wrong, correlates it with what eventually worked, and writes specific project-level learnings that prevent the same mistakes next session.

Quick Start¶

# See recommendations for current project (dry-run, no changes)
headroom learn

# Write recommendations to CLAUDE.md and MEMORY.md
headroom learn --apply

# Analyze a specific project
headroom learn --project ~/my-project --apply

# Analyze all projects
headroom learn --all --apply

How It Works¶

Past Sessions → Scanner → Analyzer → Writer → CLAUDE.md / MEMORY.md
                  │           │          │
                  │           │          └─ Writes marker-delimited sections
                  │           │             (replaced on re-run, not duplicated)
                  │           │
                  │           └─ Success Correlation: for each failure,
                  │              finds what succeeded and extracts the diff
                  │
                  └─ Reads ~/.claude/projects/*.jsonl
                     (extensible to Cursor, Codex, etc.)

Success Correlation¶

The core innovation. Instead of cataloging failures ("Read failed 5 times"), Headroom finds what the model did to fix each failure:

Failed: Read axion-formats/src/main/java/.../FirstClassEntity.java
Then succeeded: Read axion-scala-common/src/main/scala/.../FirstClassEntity.scala
Learning: "FirstClassEntity is at axion-scala-common/, not axion-formats/"

This produces specific, actionable corrections — not generic advice.

What It Learns¶

1. Environment Facts → CLAUDE.md¶

Which runtime commands work vs fail.

### Environment
- **Python**: use `uv run python` (not `python3` — modules not available outside venv)

2. File Path Corrections → CLAUDE.md¶

Wrong paths the model keeps guessing, with the correct locations.

### File Path Corrections
- `axion-common/src/.../AxionSparkConstants.scala`
  → actually at `axion-spark-common/src/.../AxionSparkConstants.scala`

3. Search Scope → CLAUDE.md¶

Which directories to search in (narrow paths fail, broader ones work).

### Search Scope
- Don't search `axion-model/` → use `axion/` (the repo root)

4. Command Patterns → CLAUDE.md¶

How commands should (and shouldn't) be run.

### Command Patterns
- **user_prefers_manual**: User rejected gradle 18 times — show the command, don't execute
- **python_runtime**: Use `uv run python` not `python3` (ModuleNotFoundError)

5. Known Large Files → CLAUDE.md¶

Files that need offset/limit with Read.

### Known Large Files
- `proxy/server.py` (~8000 lines) — always use offset/limit

6. Retry Prevention → MEMORY.md¶

Specific suggestions derived from actual corrections.

7. Permission Notes → MEMORY.md¶

Commands repeatedly rejected — model should suggest them to the user instead.

Where Learnings Go¶

Pattern	Destination	Why
Environment, paths, search scope, commands, large files	CLAUDE.md	Stable project facts, version-controllable
Missing paths, retry patterns, permissions	MEMORY.md	May change, agent-specific

CLAUDE.md lives in your project directory. MEMORY.md lives in ~/.claude/projects/*/memory/.

Marker-Based Updates¶

Headroom manages a clearly-delimited section in each file:

<!-- headroom:learn:start -->
## Headroom Learned Patterns
*Auto-generated by `headroom learn` — do not edit manually*
...
<!-- headroom:learn:end -->

On re-run, only the content between markers is replaced. Your existing file content is preserved.

Architecture¶

Scanner (adapter)  →  Analyzer (generic)  →  Writer (adapter)
├── ClaudeCodeScanner   ├── EnvironmentAnalyzer   ├── ClaudeCodeWriter
├── (CursorScanner)     ├── StructureAnalyzer     ├── (CursorWriter)
└── (GenericScanner)    ├── CommandAnalyzer        └── (GenericWriter)
                        ├── RetryAnalyzer
                        └── CrossSessionAnalyzer

Scanners read tool-specific log formats and produce normalized ToolCall sequences. Analyzers work on ToolCall — same analysis for any agent system. Writers output to tool-specific context injection mechanisms.

To add support for a new agent (e.g., Cursor): 1. Write CursorScanner(ConversationScanner) — reads Cursor's log format 2. Write CursorWriter(ContextWriter) — writes to .cursorrules 3. Same analyzers, same models, same recommendations

CLI Reference¶

headroom learn [OPTIONS]

Options:
  --project PATH    Project directory to analyze (default: current directory)
  --all             Analyze all discovered projects
  --apply           Write recommendations (default: dry-run)
  --claude-dir PATH Path to .claude directory (default: ~/.claude)

Real-World Results¶

Tested on 67,583 tool calls across 23 projects:

Metric	Value
Failure rate	7.5% (5,066 failures)
Corrections extracted	164 per project (avg)
Specific path corrections	22 (axion project)
Search scope corrections	24 (axion project)
Command patterns learned	5 (axion project)
Estimated preventable waste	~27 MB across corpus