diff --git a/.planning/REQUIREMENTS.md b/.planning/REQUIREMENTS.md
index a84747e..0cf9a00 100644
--- a/.planning/REQUIREMENTS.md
+++ b/.planning/REQUIREMENTS.md
@@ -94,31 +94,31 @@ Quali fasi coprono quali requirements. Aggiornato durante creazione roadmap.
 
 | Requirement | Phase | Status |
 |-------------|-------|--------|
-| AUTH-01 | TBD | Pending |
-| AUTH-02 | TBD | Pending |
-| AUTH-03 | TBD | Pending |
-| AUTH-04 | TBD | Pending |
-| ONBR-01 | TBD | Pending |
-| ONBR-02 | TBD | Pending |
-| CHAT-01 | TBD | Pending |
-| CHAT-02 | TBD | Pending |
-| CHAT-03 | TBD | Pending |
-| CHAT-04 | TBD | Pending |
-| CONT-01 | TBD | Pending |
-| CONT-02 | TBD | Pending |
-| CONT-03 | TBD | Pending |
-| SCHD-01 | TBD | Pending |
-| SCHD-02 | TBD | Pending |
-| SCHD-03 | TBD | Pending |
-| SCHD-04 | TBD | Pending |
-| MSGN-01 | TBD | Pending |
-| MSGN-02 | TBD | Pending |
+| AUTH-01 | Phase 1 | Pending |
+| AUTH-02 | Phase 1 | Pending |
+| AUTH-03 | Phase 1 | Pending |
+| AUTH-04 | Phase 2 | Pending |
+| ONBR-01 | Phase 3 | Pending |
+| ONBR-02 | Phase 3 | Pending |
+| CHAT-01 | Phase 4 | Pending |
+| CHAT-02 | Phase 4 | Pending |
+| CHAT-03 | Phase 4 | Pending |
+| CHAT-04 | Phase 8 | Pending |
+| CONT-01 | Phase 5 | Pending |
+| CONT-02 | Phase 5 | Pending |
+| CONT-03 | Phase 9 | Pending |
+| SCHD-01 | Phase 6 | Pending |
+| SCHD-02 | Phase 6 | Pending |
+| SCHD-03 | Phase 7 | Pending |
+| SCHD-04 | Phase 7 | Pending |
+| MSGN-01 | Phase 10 | Pending |
+| MSGN-02 | Phase 10 | Pending |
 
 **Coverage:**
 - v1 requirements: 19 total
-- Mapped to phases: 0
-- Unmapped: 19 ⚠️
+- Mapped to phases: 19
+- Unmapped: 0 ✓
 
 ---
 *Requirements defined: 2026-01-30*
-*Last updated: 2026-01-30 after initial definition*
+*Last updated: 2026-01-31 after roadmap creation*
diff --git a/.planning/ROADMAP.md b/.planning/ROADMAP.md
new file mode 100644
index 0000000..b8521ef
--- /dev/null
+++ b/.planning/ROADMAP.md
@@ -0,0 +1,194 @@
+# Roadmap: Leopost
+
+## Overview
+
+Leopost viene costruito in 10 fasi incrementali che portano da zero a un micro-SaaS AI-first funzionante. Iniziamo con fondamenta solide (auth, database, multi-tenancy), aggiungiamo integrazione social e AI, implementiamo scheduling affidabile con job queue, poi concludiamo con funzionalità avanzate (AI learning, messaging bots). Ogni fase consegna capacità verificabili dall'utente, nessun lavoro speculativo.
+
+## Phases
+
+**Phase Numbering:**
+- Integer phases (1, 2, 3): Planned milestone work
+- Decimal phases (2.1, 2.2): Urgent insertions (marked with INSERTED)
+
+Decimal phases appear between their surrounding integers in numeric order.
+
+- [ ] **Phase 1: Foundation & Auth** - User accounts, plans, multi-tenant database
+- [ ] **Phase 2: Social Platform Integration** - Facebook OAuth, Graph API setup
+- [ ] **Phase 3: Onboarding & Context** - Brand context capture, persistent memory
+- [ ] **Phase 4: AI Chat Interface** - Chat UI, multi-model support, conversation management
+- [ ] **Phase 5: Content Generation** - AI text and image generation
+- [ ] **Phase 6: Scheduling Foundation** - Post scheduling, reliable publishing with job queue
+- [ ] **Phase 7: Automation & Calendar** - Automation levels, visual calendar
+- [ ] **Phase 8: AI Learning** - AI learns user preferences from feedback
+- [ ] **Phase 9: Editorial Planning** - AI creates editorial calendar
+- [ ] **Phase 10: Messaging Integration** - Telegram and WhatsApp bot commands
+
+## Phase Details
+
+### Phase 1: Foundation & Auth
+**Goal**: Users can create accounts, log in, and subscribe to plans in a secure multi-tenant environment
+**Depends on**: Nothing (first phase)
+**Requirements**: AUTH-01, AUTH-02, AUTH-03
+**Success Criteria** (what must be TRUE):
+  1. User can register with email/password and receive confirmation email
+  2. User can log in with Google OAuth and stay authenticated across sessions
+  3. User can view and switch between Free, Creator, and Pro plans
+  4. System enforces plan-specific limits (configured in database, enforced in API)
+  5. All data is isolated per tenant (RLS active, no cross-tenant leakage)
+**Plans**: TBD
+
+Plans:
+- [ ] TBD during plan-phase
+
+### Phase 2: Social Platform Integration
+**Goal**: Users can securely connect their Facebook account for publishing
+**Depends on**: Phase 1
+**Requirements**: AUTH-04
+**Success Criteria** (what must be TRUE):
+  1. User can click "Connect Facebook" and complete OAuth flow
+  2. Facebook access token is stored securely with automatic refresh
+  3. User can view connected Facebook pages and select target page
+  4. System handles token expiration gracefully (refresh before publish)
+  5. API rate limits are monitored and logged (dashboard shows remaining quota)
+**Plans**: TBD
+
+Plans:
+- [ ] TBD during plan-phase
+
+### Phase 3: Onboarding & Context
+**Goal**: New users provide brand context that AI uses for personalized content
+**Depends on**: Phase 1
+**Requirements**: ONBR-01, ONBR-02
+**Success Criteria** (what must be TRUE):
+  1. New user sees progressive onboarding wizard (not overwhelming)
+  2. User provides business name, sector, and description in < 2 minutes
+  3. Brand context persists in database and loads in future sessions
+  4. User can update brand info anytime via settings page
+  5. AI prompts automatically inject brand context (verified in logs)
+**Plans**: TBD
+
+Plans:
+- [ ] TBD during plan-phase
+
+### Phase 4: AI Chat Interface
+**Goal**: Users interact with AI assistant to create content via natural conversation
+**Depends on**: Phase 3
+**Requirements**: CHAT-01, CHAT-02, CHAT-03
+**Success Criteria** (what must be TRUE):
+  1. User sees chat interface as main screen (not buried in tabs)
+  2. User can send message and receive AI response in < 5 seconds
+  3. User can choose AI model (GPT, Claude, Gemini) in settings
+  4. AI suggests 3-5 initial actions after onboarding (e.g., "Create first post")
+  5. Conversation history persists (user can scroll back, AI remembers context)
+**Plans**: TBD
+
+Plans:
+- [ ] TBD during plan-phase
+
+### Phase 5: Content Generation
+**Goal**: AI generates quality text posts and images adapted to brand voice
+**Depends on**: Phase 4
+**Requirements**: CONT-01, CONT-02
+**Success Criteria** (what must be TRUE):
+  1. User asks "Create post about [topic]" and receives text draft in < 10 seconds
+  2. Generated post uses brand context (tone, sector, target audience)
+  3. User asks "Add image" and receives AI-generated image in < 30 seconds
+  4. User can regenerate content with feedback ("Make it more casual")
+  5. Generated content displays in chat with edit capability
+**Plans**: TBD
+
+Plans:
+- [ ] TBD during plan-phase
+
+### Phase 6: Scheduling Foundation
+**Goal**: Users reliably schedule posts and they publish automatically at specified time
+**Depends on**: Phase 2, Phase 5
+**Requirements**: SCHD-01, SCHD-02
+**Success Criteria** (what must be TRUE):
+  1. User can set date/time for post and it saves to queue
+  2. Post publishes to Facebook automatically at scheduled time (99%+ reliability)
+  3. User receives notification when post is published (or if it fails)
+  4. Job queue handles retries with exponential backoff (API failures don't lose posts)
+  5. Timezone is handled correctly (user sees local time, system schedules in UTC)
+**Plans**: TBD
+
+Plans:
+- [ ] TBD during plan-phase
+
+### Phase 7: Automation & Calendar
+**Goal**: Users configure automation level and visualize scheduled posts in calendar
+**Depends on**: Phase 6
+**Requirements**: SCHD-03, SCHD-04
+**Success Criteria** (what must be TRUE):
+  1. User can set automation level (Approval → Semi-Auto → Autopilot)
+  2. In Approval mode, AI generates drafts and user must manually approve
+  3. In Autopilot mode, AI generates and publishes without user action
+  4. Calendar view shows all scheduled posts (color-coded by platform)
+  5. User can drag-and-drop posts to reschedule in calendar
+**Plans**: TBD
+
+Plans:
+- [ ] TBD during plan-phase
+
+### Phase 8: AI Learning
+**Goal**: AI improves content quality over time by learning user's authentic voice
+**Depends on**: Phase 7
+**Requirements**: CHAT-04
+**Success Criteria** (what must be TRUE):
+  1. User can give thumbs up/down feedback on generated content
+  2. AI analyzes approved posts to identify tone, vocabulary, structure patterns
+  3. Future posts incorporate learned preferences (measurably more "on brand")
+  4. User sees improvement notification ("AI learned from 10 approved posts")
+  5. Learning data is per-tenant (AI doesn't leak patterns across users)
+**Plans**: TBD
+
+Plans:
+- [ ] TBD during plan-phase
+
+### Phase 9: Editorial Planning
+**Goal**: AI proactively creates multi-week content calendar aligned to business goals
+**Depends on**: Phase 8
+**Requirements**: CONT-03
+**Success Criteria** (what must be TRUE):
+  1. User asks "Create 2-week plan" and AI generates calendar with 10-14 post ideas
+  2. Editorial plan includes diverse content types (educational, promotional, engagement)
+  3. User can accept entire plan or edit individual posts
+  4. Accepted plan populates calendar with draft posts (ready to review/publish)
+  5. AI considers business context (sector trends, user's past successful posts)
+**Plans**: TBD
+
+Plans:
+- [ ] TBD during plan-phase
+
+### Phase 10: Messaging Integration
+**Goal**: Users can create and schedule posts via Telegram or WhatsApp commands
+**Depends on**: Phase 6
+**Requirements**: MSGN-01, MSGN-02
+**Success Criteria** (what must be TRUE):
+  1. User connects Telegram bot and can send "/create [topic]" to generate post
+  2. Telegram bot responds with draft post and options (edit, schedule, publish now)
+  3. User connects WhatsApp bot (Business API verified) with same functionality
+  4. Both bots support voice messages (transcribed to text, processed by AI)
+  5. Posts created via messaging appear in web calendar (sync across channels)
+**Plans**: TBD
+
+Plans:
+- [ ] TBD during plan-phase
+
+## Progress
+
+**Execution Order:**
+Phases execute in numeric order: 1 → 2 → 3 → 4 → 5 → 6 → 7 → 8 → 9 → 10
+
+| Phase | Plans Complete | Status | Completed |
+|-------|----------------|--------|-----------|
+| 1. Foundation & Auth | 0/TBD | Not started | - |
+| 2. Social Platform Integration | 0/TBD | Not started | - |
+| 3. Onboarding & Context | 0/TBD | Not started | - |
+| 4. AI Chat Interface | 0/TBD | Not started | - |
+| 5. Content Generation | 0/TBD | Not started | - |
+| 6. Scheduling Foundation | 0/TBD | Not started | - |
+| 7. Automation & Calendar | 0/TBD | Not started | - |
+| 8. AI Learning | 0/TBD | Not started | - |
+| 9. Editorial Planning | 0/TBD | Not started | - |
+| 10. Messaging Integration | 0/TBD | Not started | - |
diff --git a/.planning/STATE.md b/.planning/STATE.md
new file mode 100644
index 0000000..90f2854
--- /dev/null
+++ b/.planning/STATE.md
@@ -0,0 +1,69 @@
+# Project State
+
+## Project Reference
+
+See: .planning/PROJECT.md (updated 2026-01-30)
+
+**Core value:** L'AI fa il lavoro sporco del social media manager — minimo sforzo, massima resa
+**Current focus:** Phase 1 - Foundation & Auth
+
+## Current Position
+
+Phase: 1 of 10 (Foundation & Auth)
+Plan: 0 of TBD (planning not started)
+Status: Ready to plan
+Last activity: 2026-01-31 — Roadmap created with 10 phases, 100% requirement coverage
+
+Progress: [░░░░░░░░░░] 0%
+
+## Performance Metrics
+
+**Velocity:**
+- Total plans completed: 0
+- Average duration: N/A
+- Total execution time: 0.0 hours
+
+**By Phase:**
+
+| Phase | Plans | Total | Avg/Plan |
+|-------|-------|-------|----------|
+| - | - | - | - |
+
+**Recent Trend:**
+- Last 5 plans: N/A
+- Trend: N/A
+
+*Updated after each plan completion*
+
+## Accumulated Context
+
+### Decisions
+
+Decisions are logged in PROJECT.md Key Decisions table.
+Recent decisions affecting current work:
+
+- Initial: Chat-first con schermate di supporto (L'interazione naturale riduce l'attrito)
+- Initial: Multi-model AI (Diversi utenti preferiscono modelli diversi, evita lock-in)
+- Initial: Onboarding progressivo (Evita abbandono per "troppo da fare" al primo accesso)
+- Initial: Automazione configurabile (Costruisce fiducia gradualmente, dall'approval all'autopilot)
+- Initial: Headless architecture (Prepara per app native senza riscrivere logica)
+
+### Pending Todos
+
+None yet.
+
+### Blockers/Concerns
+
+**Research-identified risks to address early:**
+- Phase 1: Implement RLS multi-tenant isolation from day 1 (no retrofitting)
+- Phase 2: Facebook API rate limits (200 DM/hour) — need exponential backoff + monitoring
+- Phase 5: AI cost management — implement caching, freemium limits, per-user tracking
+- Phase 6: Job queue reliability critical — BullMQ on Redis, not setTimeout
+- Phase 10: WhatsApp Business verification takes 2-4 weeks — start process early
+
+## Session Continuity
+
+Last session: 2026-01-31
+Stopped at: Roadmap and STATE.md created, traceability updated
+Resume file: None
+Next step: Execute `/gsd:plan-phase 1` to create detailed plans for Foundation & Auth