diff --git a/.planning/REQUIREMENTS.md b/.planning/REQUIREMENTS.md
index 67cd615..7eaf6bf 100644
--- a/.planning/REQUIREMENTS.md
+++ b/.planning/REQUIREMENTS.md
@@ -71,27 +71,27 @@ Which phases cover which requirements. Updated during roadmap creation.
 
 | Requirement | Phase | Status |
 |-------------|-------|--------|
-| DECO-01 | — | Pending |
-| DECO-02 | — | Pending |
-| DECO-03 | — | Pending |
-| DECO-04 | — | Pending |
-| DECO-05 | — | Pending |
-| DECO-06 | — | Pending |
-| DECO-07 | — | Pending |
-| DECO-08 | — | Pending |
-| CONF-01 | — | Pending |
-| CONF-02 | — | Pending |
-| CONF-03 | — | Pending |
-| DASH-01 | — | Pending |
-| DASH-02 | — | Pending |
-| DASH-03 | — | Pending |
-| DASH-04 | — | Pending |
-| DASH-05 | — | Pending |
+| DECO-01 | Phase 1 | Pending |
+| DECO-02 | Phase 1 | Pending |
+| DECO-03 | Phase 1 | Pending |
+| DECO-04 | Phase 1 | Pending |
+| DECO-05 | Phase 1 | Pending |
+| DECO-06 | Phase 1 | Pending |
+| DECO-07 | Phase 1 | Pending |
+| DECO-08 | Phase 1 | Pending |
+| CONF-01 | Phase 2 | Pending |
+| CONF-02 | Phase 2 | Pending |
+| CONF-03 | Phase 2 | Pending |
+| DASH-01 | Phase 3 | Pending |
+| DASH-02 | Phase 3 | Pending |
+| DASH-03 | Phase 3 | Pending |
+| DASH-04 | Phase 3 | Pending |
+| DASH-05 | Phase 3 | Pending |
 
 **Coverage:**
 - v1 requirements: 16 total
-- Mapped to phases: 0
-- Unmapped: 16
+- Mapped to phases: 16
+- Unmapped: 0
 
 ---
 *Requirements defined: 2026-02-09*
diff --git a/.planning/ROADMAP.md b/.planning/ROADMAP.md
new file mode 100644
index 0000000..b4b66ce
--- /dev/null
+++ b/.planning/ROADMAP.md
@@ -0,0 +1,66 @@
+# Roadmap: Flynn Operator DX
+
+**Created:** 2026-02-09
+**Depth:** Quick (3 phases)
+**Core Value:** Make Flynn easier to reason about, configure, and monitor
+
+## Overview
+
+Three phases, each delivering one complete capability. Phase 1 decomposes the monolithic daemon wiring file into focused modules — this must happen first because Phases 2 and 3 both touch daemon internals. Phase 2 adds multi-environment config overlays. Phase 3 builds the live ops dashboard with real-time metrics.
+
+## Phases
+
+### Phase 1: Daemon Decomposition
+
+**Goal:** daemon/index.ts is a thin composition root; each concern lives in its own module with the same public interface.
+
+**Dependencies:** None (first phase)
+
+**Requirements:** DECO-01, DECO-02, DECO-03, DECO-04, DECO-05, DECO-06, DECO-07, DECO-08
+
+**Success Criteria:**
+1. Running `pnpm test:run` passes 1077+ tests with zero regressions
+2. daemon/index.ts is under 200 lines and contains only imports, wiring, and lifecycle — no business logic
+3. Each extracted module (models, channels, agents, memory, tools, routing) can be understood in isolation — reading one file tells you everything about that concern
+4. Adding a new model provider or channel adapter requires editing the relevant module file, not daemon/index.ts
+
+### Phase 2: Config Overlays
+
+**Goal:** Operator can manage dev/docker/production configs with a base file plus lightweight overlay files, selected by environment variable.
+
+**Dependencies:** Phase 1 (daemon is decomposed; config loading changes are lower risk)
+
+**Requirements:** CONF-01, CONF-02, CONF-03
+
+**Success Criteria:**
+1. Setting `FLYNN_ENV=docker` and starting Flynn loads config/docker.yaml merged on top of the base config — operator sees docker-specific settings active
+2. Starting Flynn without FLYNN_ENV works exactly as before — existing config files unchanged, zero breakage
+3. Running `flynn doctor` with `FLYNN_ENV=staging` (no staging.yaml) reports a clear error identifying the missing overlay file
+
+### Phase 3: Live Ops Dashboard
+
+**Goal:** Operator can open the web dashboard and see real-time system health — counters, model performance, event stream, and active requests — without tailing logs.
+
+**Dependencies:** Phase 1 (metrics hooks need to be wired into decomposed modules, not the god file)
+
+**Requirements:** DASH-01, DASH-02, DASH-03, DASH-04, DASH-05
+
+**Success Criteria:**
+1. Opening the dashboard shows live-updating counters for messages processed, active sessions, queue depth, and uptime — values change in real time as messages flow
+2. After sending a message through any channel, the model call appears in the dashboard with latency, tokens/sec, and provider name within seconds
+3. Triggering an error (e.g., bad model config) shows the error in the dashboard event stream with timestamp and context — no need to check terminal output
+4. Hitting GET /health returns JSON with daemon status, uptime, and component readiness — usable for Docker HEALTHCHECK or monitoring
+
+## Progress
+
+| Phase | Status | Requirements |
+|-------|--------|--------------|
+| 1 — Daemon Decomposition | not_started | DECO-01..08 (8) |
+| 2 — Config Overlays | not_started | CONF-01..03 (3) |
+| 3 — Live Ops Dashboard | not_started | DASH-01..05 (5) |
+
+**Coverage:** 16/16 v1 requirements mapped ✓
+
+---
+*Roadmap created: 2026-02-09*
+*Last updated: 2026-02-09*
diff --git a/.planning/STATE.md b/.planning/STATE.md
new file mode 100644
index 0000000..ee4511f
--- /dev/null
+++ b/.planning/STATE.md
@@ -0,0 +1,58 @@
+# State: Flynn Operator DX
+
+## Project Reference
+
+**Core Value:** Make Flynn easier to reason about, configure, and monitor
+**Milestone:** Operator DX
+**Phases:** 3
+
+## Current Position
+
+**Phase:** 1 — Daemon Decomposition
+**Plan:** Not yet created
+**Status:** not_started
+**Progress:** ░░░░░░░░░░ 0/3 phases
+
+## Phase Status
+
+| Phase | Status | Plans |
+|-------|--------|-------|
+| 1 — Daemon Decomposition | not_started | — |
+| 2 — Config Overlays | not_started | — |
+| 3 — Live Ops Dashboard | not_started | — |
+
+## Performance Metrics
+
+| Metric | Value |
+|--------|-------|
+| Test count | 1077 (baseline) |
+| daemon/index.ts lines | 1087 (baseline) |
+
+## Accumulated Context
+
+### Key Decisions
+- Decompose god file incrementally, not rewrite
+- Config overlays over separate files
+- Extend existing vanilla JS dashboard
+- Skip structured logging — dashboard will reveal what metrics matter
+
+### Technical Notes
+- daemon/index.ts handles: model clients, channel setup, agent factory, memory init, vector store, session pruning, lifecycle, shutdown
+- Existing routing test file exists (decomposition already partially anticipated)
+- Web dashboard is vanilla JS SPA at src/gateway/ui/
+- Config loader at src/config/loader.ts, schema at src/config/schema.ts (409 lines)
+
+### TODOs
+_(none yet)_
+
+### Blockers
+_(none)_
+
+## Session Continuity
+
+**Last session:** Initial roadmap creation
+**Next action:** Plan Phase 1 (Daemon Decomposition)
+
+---
+*State initialized: 2026-02-09*
+*Last updated: 2026-02-09*