obsidian-rag/docs/superpowers/specs/2026-04-10-obsidian-rag-task-list.md

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

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Phase 0: Project Scaffolding & Environment

0.1 Repository & Build Setup

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

0.2 Environment Validation

• 0.2.1 Verify Ollama + mxbai-embed-large (S) - Test embedding API
• 0.2.2 Verify LanceDB Python package (S) - Test table creation and queries
• 0.2.3 Verify sample vault accessibility (S) - Count .md files in KnowledgeVault

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Phase 1: Data Layer (Python Indexer)

1.1 Configuration (Python)

• 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

• 1.2.1 Implement path traversal prevention (S) - Depends on 1.1.1 - Validate paths, reject ../ and symlinks
• 1.2.2 Implement input sanitization (S) - Depends on 1.1.1 - Strip HTML, normalize whitespace
• 1.2.3 Implement sensitive content detection (S) - Depends on 1.1.1 - Detect health/financial/relations content
• 1.2.4 Implement directory access control (S) - Depends on 1.1.1 - Apply deny/allow lists
• 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

• 1.3.1 Implement markdown parser (S) - Depends on 0.1.2 - Parse frontmatter, headings, tags
• 1.3.2 Implement structured chunker (M) - Depends on 1.3.1 - Split by section headers
• 1.3.3 Implement sliding window chunker (S) - Depends on 1.3.1 - 500 token window with overlap
• 1.3.4 Implement chunk router (S) - Depends on 1.3.2, 1.3.3 - Route structured vs unstructured
• 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

• 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

• 1.5.1 Implement LanceDB table creation (S) - Depends on 0.2.2 - Create obsidian_chunks table
• 1.5.2 Implement vector upsert (S) - Depends on 1.5.1 - Add/update chunks
• 1.5.3 Implement vector delete (S) - Depends on 1.5.1 - Remove by source_file
• 1.5.4 Implement vector search (M) - Depends on 1.5.1 - Query with filters
• 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

• 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
• 1.6.2 Implement incremental sync (M) - Depends on 1.6.1, 1.5.3 - Compare mtime, process changes
• 1.6.3 Implement reindex (S) - Depends on 1.6.1 - Drop table + rebuild
• 1.6.4 Implement sync-result.json writer (S) - Depends on 1.6.1 - Atomic file writing
• 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

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Phase 2: Data Layer (TypeScript Client)

2.1 Configuration (TypeScript) - Can start after 0.1.1, parallel with Phase 1

• 2.1.1 Implement config loader (S) - Depends on 0.1.1 - Read JSON, validate schema
• 2.1.2 Implement config types (S) - Depends on 2.1.1 - TypeScript interfaces

2.2 LanceDB Client - Depends on Phase 1 completion

• 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

• 2.3.1 Implement subprocess spawner (M) - Depends on 0.1.1 - Spawn Python CLI
• 2.3.2 Implement sync-result reader (S) - Depends on 2.3.1 - Read sync results
• 2.3.3 Implement job tracking (S) - Depends on 2.3.1 - Track progress

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Phase 3: Session & Transport Layers

3.1 Health State Machine - Depends on Phase 2

• 3.1.1 Implement health prober (S) - Depends on 2.1.1, 2.2.1 - Probe dependencies
• 3.1.2 Implement state machine (S) - Depends on 3.1.1 - HEALTHY/DEGRADED/UNAVAILABLE
• 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

• 3.2.1 Implement file watcher (S) - Depends on 2.1.1 - Watch vault directory
• 3.2.2 Implement debounce & batching (M) - Depends on 3.2.1 - Batch changes
• 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

• 3.3.1 Implement response envelope factory (S) - Depends on 0.1.1 - Build response structure
• 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

• 3.4.1 Implement directory filter validator (S) - Depends on 2.1.1 - Validate filters
• 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

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Phase 4: Tool Layer

4.1 Tool Implementations - Depends on Phase 3

• [~] 4.1.1 Implement obsidian_rag_search tool (M) - Depends on 2.2.1, 3.3.1, 3.4.2 - Search with filters ⚠️ LanceDB TS client now wired, needs OpenClaw integration
• [~] 4.1.2 Implement obsidian_rag_index tool (M) - Depends on 2.3.1, 2.3.3, 3.3.1 - Spawn indexer ⚠️ stub — tool registration not wired to OpenClaw
• [~] 4.1.3 Implement obsidian_rag_status tool (S) - Depends on 3.1.2, 2.3.2, 3.3.1 - Return health status ⚠️ stub — reads sync-result not LanceDB stats
• [~] 4.1.4 Implement obsidian_rag_memory_store tool (S) - Depends on 3.3.1 - Persist to memory ⚠️ stub — no-op
• 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

• [~] 4.2.1 Implement plugin entry point (M) - Depends on 4.1.1-4.1.4, 3.2.3, 3.1.2 - Plugin lifecycle ⚠️ stub — tools registration is a TODO
• 4.2.2 Verify OpenClaw plugin lifecycle (S) - Depends on 4.2.1 - Manual test

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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

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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	1	5	1	0
Phase 5: Integration	12	0	12	0	0
Total	64	40	20	5	0

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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