# Obsidian RAG Plugin - Work Queue

**Date:** 2026-04-10
**Based on:** Work Breakdown Structure v1.0
**Last Updated:** 2026-04-10 21:30

## Legend
- `[ ]` = Pending
- `[x]` = Done
- `[~]` = In Progress
- `[!]` = Error / Blocked

---

## Phase 0: Project Scaffolding & Environment

### 0.1 Repository & Build Setup
- [x] **0.1.1** Initialize TypeScript project structure (S) - Create package.json, tsconfig.json, src/ directory
- [x] **0.1.2** Initialize Python package structure (S) - Create pyproject.toml, obsidian_rag/ module skeleton
- [x] **0.1.3** Create development config file (S) - Depends on 0.1.1 - Create ./obsidian-rag/config.json
- [x] **0.1.4** Set up OpenClaw plugin manifest (S) - Depends on 0.1.1 - Create openclaw.plugin.json
- [x] **0.1.5** Configure test runners (S) - Depends on 0.1.1, 0.1.2 - Setup vitest and pytest configs

### 0.2 Environment Validation
- [x] **0.2.1** Verify Ollama + mxbai-embed-large (S) - Test embedding API
- [x] **0.2.2** Verify LanceDB Python package (S) - Test table creation and queries
- [x] **0.2.3** Verify sample vault accessibility (S) - Count .md files in KnowledgeVault

---

## Phase 1: Data Layer (Python Indexer)

### 1.1 Configuration (Python)
- [x] **1.1.1** Implement config loader (S) - Depends on 0.1.2 - Read JSON, resolve paths, validate schema
- [ ] **1.1.2** Write config tests (S) - Depends on 1.1.1 - Test validation and path resolution

### 1.2 Security (Python) - Can start after 1.1.1, parallel with other components
- [x] **1.2.1** Implement path traversal prevention (S) - Depends on 1.1.1 - Validate paths, reject ../ and symlinks
- [x] **1.2.2** Implement input sanitization (S) - Depends on 1.1.1 - Strip HTML, normalize whitespace
- [x] **1.2.3** Implement sensitive content detection (S) - Depends on 1.1.1 - Detect health/financial/relations content
- [x] **1.2.4** Implement directory access control (S) - Depends on 1.1.1 - Apply deny/allow lists
- [x] **1.2.5** Write security tests (M) - Depends on 1.2.1-1.2.4 - Test all security functions

### 1.3 Chunking - Can start after 1.1.1, parallel with security
- [x] **1.3.1** Implement markdown parser (S) - Depends on 0.1.2 - Parse frontmatter, headings, tags
- [x] **1.3.2** Implement structured chunker (M) - Depends on 1.3.1 - Split by section headers
- [x] **1.3.3** Implement sliding window chunker (S) - Depends on 1.3.1 - 500 token window with overlap
- [x] **1.3.4** Implement chunk router (S) - Depends on 1.3.2, 1.3.3 - Route structured vs unstructured
- [x] **1.3.5** Write chunker tests (M) - Depends on 1.3.4 - Test all chunking scenarios

### 1.4 Embedding - Can start after 1.1.1, parallel with chunking/security
- [x] **1.4.1** Implement Ollama embedder (M) - Depends on 1.1.1 - Batch 64 chunks, error handling
- [ ] **1.4.2** Implement embedding cache (S) - Depends on 1.4.1 - File-based cache
- [ ] **1.4.3** Write embedder tests (S) - Depends on 1.4.1, 1.4.2 - Test batching and cache

### 1.5 Vector Store - Can start after 0.2.2, parallel with other components
- [x] **1.5.1** Implement LanceDB table creation (S) - Depends on 0.2.2 - Create obsidian_chunks table
- [x] **1.5.2** Implement vector upsert (S) - Depends on 1.5.1 - Add/update chunks
- [x] **1.5.3** Implement vector delete (S) - Depends on 1.5.1 - Remove by source_file
- [x] **1.5.4** Implement vector search (M) - Depends on 1.5.1 - Query with filters
- [x] **1.5.5** Write vector store tests (M) - Depends on 1.5.2-1.5.4 - Test CRUD operations

### 1.6 Indexer Pipeline & CLI - Depends on multiple components
- [x] **1.6.1** Implement full index pipeline (M) - Depends on 1.2.4, 1.3.4, 1.4.1, 1.5.2 - Scan → parse → chunk → embed → store
- [x] **1.6.2** Implement incremental sync (M) - Depends on 1.6.1, 1.5.3 - Compare mtime, process changes
- [x] **1.6.3** Implement reindex (S) - Depends on 1.6.1 - Drop table + rebuild
- [x] **1.6.4** Implement sync-result.json writer (S) - Depends on 1.6.1 - Atomic file writing
- [x] **1.6.5** Implement CLI entry point (M) - Depends on 1.6.1, 1.6.2, 1.6.3 - index/sync/reindex commands
- [ ] **1.6.6** Write indexer tests (M) - Depends on 1.6.5 - Test full pipeline and CLI

---

## Phase 2: Data Layer (TypeScript Client)

### 2.1 Configuration (TypeScript) - Can start after 0.1.1, parallel with Phase 1
- [x] **2.1.1** Implement config loader (S) - Depends on 0.1.1 - Read JSON, validate schema
- [x] **2.1.2** Implement config types (S) - Depends on 2.1.1 - TypeScript interfaces

### 2.2 LanceDB Client - Depends on Phase 1 completion
- [x] **2.2.1** Implement LanceDB query client (M) - Depends on 0.1.1 - Connect and search
- [~] **2.2.2** Implement full-text search fallback (S) - Depends on 2.2.1 - Degraded mode

### 2.3 Indexer Bridge - Depends on Phase 1 completion
- [x] **2.3.1** Implement subprocess spawner (M) - Depends on 0.1.1 - Spawn Python CLI
- [x] **2.3.2** Implement sync-result reader (S) - Depends on 2.3.1 - Read sync results
- [x] **2.3.3** Implement job tracking (S) - Depends on 2.3.1 - Track progress

---

## Phase 3: Session & Transport Layers

### 3.1 Health State Machine - Depends on Phase 2
- [x] **3.1.1** Implement health prober (S) - Depends on 2.1.1, 2.2.1 - Probe dependencies
- [x] **3.1.2** Implement state machine (S) - Depends on 3.1.1 - HEALTHY/DEGRADED/UNAVAILABLE
- [x] **3.1.3** Implement staleness detector (S) - Depends on 3.1.2, 2.3.2 - Detect stale syncs

### 3.2 Vault Watcher - Depends on Phase 2
- [x] **3.2.1** Implement file watcher (S) - Depends on 2.1.1 - Watch vault directory
- [x] **3.2.2** Implement debounce & batching (M) - Depends on 3.2.1 - Batch changes
- [x] **3.2.3** Implement auto-sync trigger (M) - Depends on 3.2.2, 2.3.1, 3.1.2 - Trigger sync
- [ ] **3.2.4** Write vault watcher tests (M) - Depends on 3.2.3 - Test watcher behavior

### 3.3 Response Envelope & Error Normalization - Can start after 0.1.1, parallel
- [x] **3.3.1** Implement response envelope factory (S) - Depends on 0.1.1 - Build response structure
- [x] **3.3.2** Implement error normalizer (S) - Depends on 3.3.1 - Map exceptions to codes

### 3.4 Security Guard (TypeScript) - Can start after 2.1.1, parallel with 3.1-3.2
- [x] **3.4.1** Implement directory filter validator (S) - Depends on 2.1.1 - Validate filters
- [x] **3.4.2** Implement sensitive content flag (S) - Depends on 3.4.1 - Flag sensitive content
- [ ] **3.4.3** Write security guard tests (S) - Depends on 3.4.2 - Test security functions

---

## Phase 4: Tool Layer

### 4.1 Tool Implementations - Depends on Phase 3
- [x] **4.1.1** Implement obsidian_rag_search tool (M) - Depends on 2.2.1, 3.3.1, 3.4.2 - Search with filters — LanceDB wired, OpenClaw AnyAgentTool factory
- [x] **4.1.2** Implement obsidian_rag_index tool (M) - Depends on 2.3.1, 2.3.3, 3.3.1 - Spawn indexer — wired to OpenClaw
- [x] **4.1.3** Implement obsidian_rag_status tool (S) - Depends on 3.1.2, 2.3.2, 3.3.1 - Return health status — wired to OpenClaw
- [x] **4.1.4** Implement obsidian_rag_memory_store tool (S) - Depends on 3.3.1 - Persist to memory — stub (logs to console, memory integration deferred)
- [ ] **4.1.5** Write tool unit tests (M) - Depends on 4.1.1-4.1.4 - Test all tools

### 4.2 Plugin Registration - Depends on tools
- [x] **4.2.1** Implement plugin entry point (M) - Depends on 4.1.1-4.1.4, 3.2.3, 3.1.2 - Plugin lifecycle — registerTools() using AnyAgentTool factory pattern, build clean

---

## Phase 5: Integration & Hardening

### 5.1 Integration Tests - Depends on Phase 4
- [ ] **5.1.1** Full pipeline integration test (M) - Depends on 1.6.5, 4.2.1 - Index → search
- [ ] **5.1.2** Sync cycle integration test (M) - Depends on 3.2.3, 5.1.1 - Modify → auto-sync → search
- [ ] **5.1.3** Health state integration test (S) - Depends on 3.1.2, 5.1.1 - Test state transitions
- [ ] **5.1.4** OpenClaw protocol integration test (M) - Depends on 4.2.1 - Test all tools

### 5.2 Security Test Suite - Depends on relevant components
- [ ] **5.2.1** Path traversal tests (S) - Depends on 1.2.1, 3.4.1 - Test ../, symlinks, Windows paths
- [ ] **5.2.2** XSS prevention tests (S) - Depends on 1.2.2 - Test HTML injection
- [ ] **5.2.3** Prompt injection tests (S) - Depends on 4.1.1 - Test malicious content
- [ ] **5.2.4** Network audit test (S) - Depends on 1.4.1 - Verify no outbound requests
- [ ] **5.2.5** Sensitive content tests (S) - Depends on 1.2.3, 3.4.2 - Test detection and flagging

### 5.3 Documentation & Publishing - Depends on integration tests
- [ ] **5.3.1** Write README (S) - Depends on 4.2.1 - Usage and setup docs
- [ ] **5.3.2** Create SKILL.md (S) - Depends on 4.2.1 - Skill manifest
- [ ] **5.3.3** Publish to ClawHub (S) - Depends on 5.1.1-5.2.5 - Publish skill

---

## Progress Summary

| Phase | Tasks | Done | Pending | In Progress | Blocked |
|-------|-------|------|---------|-------------|---------|
| Phase 0: Scaffolding | 8 | 8 | 0 | 0 | 0 |
| Phase 1: Python Indexer | 20 | 16 | 2 | 2 | 0 |
| Phase 2: TS Client | 7 | 6 | 0 | 1 | 0 |
| Phase 3: Session/Transport | 10 | 8 | 1 | 1 | 0 |
| Phase 4: Tool Layer | 7 | 5 | 2 | 0 | 0 |
| Phase 5: Integration | 12 | 0 | 12 | 0 | 0 |
| **Total** | **64** | **40** | **20** | **5** | **0** |

---

## Critical Path

1. Phase 0 → Phase 1 → Phase 2 → Phase 3 → Phase 4 → Phase 5
2. 0.1.1-0.1.5 → 1.1.1 → 1.3.1 → 1.6.1 → 2.2.1 → 3.1.1 → 3.2.1 → 4.1.1 → 4.2.1 → 5.1.1

## Parallel Work Opportunities

- **After 1.1.1**: Security (1.2), Chunking (1.3), Embedding (1.4) can work in parallel
- **After 0.2.2**: Vector Store (1.5) can work in parallel with other components
- **After 0.1.1**: TypeScript Config (2.1) can start early
- **Phase 3**: Response Envelope (3.3) and Security Guard (3.4) can work in parallel with Health (3.1) and Watcher (3.2)

## Effort Estimates

- **Small tasks (S)**: 31 tasks (~1-2 sessions each)
- **Medium tasks (M)**: 27 tasks (~3-5 sessions each)
- **Total**: 76-123 sessions across all phases