# HoffDesk Master Roadmap
**Last Updated:** 2026-04-25 13:59 UTC  
**Owner:** Matt (Director)  
**Agents:** Wadsworth 📋 | Socrates 🧠 | Daedalus 🎨

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## 🎯 Active Projects Overview

| Project | Status | Lead | Priority |
|---------|--------|------|----------|
| **HoffDesk Web Platform** | 🟡 In Progress | All | P0 |
| ├─ Blog Module | ✅ Phase 3 Complete | Socrates/Daedalus | - |
| ├─ Family Dashboard | 🟡 Phase 1.5 In Progress | Daedalus/Socrates | - |
| ├─ Starlette Host Routing | 🟡 Deployed (needs restart) | Socrates | - |
| **Project Icarus** | 🟢 Staging Setup Complete | Socrates/Daedalus | P1 |
| **Stock Market Daily Brief** | ⏸️ Blocked (awaiting input) | Wadsworth → Socrates | P2 |
| **Structured Logging** | 🟢 Phase 1-2 Active | Wadsworth | P3 |
| **Appliance Productization** | 🟡 Icarus active | Future | P4 |

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## ✅ COMPLETED — Last 30 Days

### Infrastructure & Security
- ✅ Cloudflare Tunnel configured (`*.hoffdesk.com` → Beelink)
- ✅ Radicale CalDAV server (port 5232, Tailscale-bound)
- ✅ Session-based auth (cookies for humans, Bearer for machines)
- ✅ Role-based access (admin vs family)
- ✅ UFW firewall (Tailscale-only SSH)
- ✅ Backup strategy (daily 7 AM → Gaming PC via Tailscale)
- ✅ Auth circuit breaker (3 failures → alert + silence)

### Blog Module (Phase 1-3 Complete)
- ✅ 13 API routes + 36 tests passing
- ✅ 7 Jinja2 templates + CSS (Daedalus)
- ✅ Content pipeline v2 (Magic Wand + Struggle)
- ✅ Admin panel with session auth
- ✅ RSS, sitemap, image upload
- ✅ Deployed to `notes.hoffdesk.com`

### Dashboard (Phase 1)
- ✅ Dashboard HTML/CSS (Daedalus)
- ✅ Jinja2 conversion (base.html.j2 + index.html.j2)
- ✅ Login page for Aundrea
- ✅ `/family/events/removed` endpoint (Bearer token)
- ✅ Recently removed events widget

### Domain Architecture
- ✅ `notes.hoffdesk.com` → blog (port 8000)
- ✅ `family.hoffdesk.com` → dashboard (port 8000 via Host routing)
- ✅ `api.hoffdesk.com` → JSON API
- ✅ `cal.hoffdesk.com` → Radicale
- ✅ `hook.hoffdesk.com` → webhooks
- ✅ Starlette Host-based routing code (main_v2.py)
- ✅ Cloudflare config updated (single port)

### Agent Configuration
- ✅ Multi-model architecture (Wadsworth/Socrates/Daedalus)
- ✅ Daedalus model: `minimax-m2.7:cloud` → `deepseek-v4:cloud` (just updated)
- ✅ Socrates model: `kimi-k2.6:cloud`
- ✅ Inter-agent protocol (sessions_send/spawn, shared/ directory)

### Automation
- ✅ Email pipeline v2 (smart classification)
- ✅ Email Worker v3 deployed (Cloudflare Email Routing → hook.hoffdesk.com)
- ✅ Conflict detection (calendar overlap scanning)
- ✅ Location cache + Hermes integration (travel time alerts)
- ✅ Heartbeat checks (30-min + daily)
- ✅ Cron jobs: `heartbeat:check`, `heartbeat:daily`, `family:daily-brief`

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## 🚧 IN PROGRESS — Current Sprint (Apr 24-25)

### 🔴 CRITICAL: Starlette Host Routing Rollout
**Status:** Code complete, service NOT switched

| Task | Status | Owner | Blocker |
|------|--------|-------|---------|
| `main_v2.py` with Host() routing | ✅ Complete | Socrates | - |
| `hoffdesk.com` apex DNS | ✅ **FIXED** | Daedalus | - |
| systemd service update | ✅ **FIXED** | Matt | - |
| Import error (`Path` in auth/router.py) | ✅ **FIXED** | Wadsworth | - |
| Service restart & verify | ⏳ **NEEDS RESTART** | Matt | sudo access |

**Files:**
- Code: `workspace-socrates/hoffdesk-api/main_v2.py`
- Service: `/etc/systemd/system/hoffdesk-api.service`
- Config: `~/.cloudflared/config.yml`

### 🟢 Project Icarus — Staging Environment
**Status:** Environment initialized, awaiting hard fork

| Component | Status | Details |
|-----------|--------|---------|
| Directory structure | ✅ Created | `services/icarus/` |
| Staging config | ✅ Created | `staging.env` with isolated paths |
| Model gate | ✅ Created | 3B restriction enforced |
| Telegram bot | ✅ Created | @IcarusTestBot (t.me/IcarusTestBot) |
| Cloudflare route | ⏳ Pending | `icarus-test.hoffdesk.com` → port 8001 |
| Hard fork (copy) | ⏳ Pending | Socrates to copy from `family_assistant/` |
| systemd service | ⏳ Pending | `icarus-staging.service` on port 8001 |

**Director Mandates:**
1. **Hard fork only** — Copy, do not extract or refactor production code
2. **3B models only** on staging — Gaming PC via Tailscale, qwen2.5:3b/llama3.2:3b
3. **Route priority** — Specific `icarus-test.hoffdesk.com` before wildcard `*.hoffdesk.com`

**Files:**
- Config: `services/icarus/staging.env`
- README: `services/icarus/README.md`
- Model gate: `services/icarus/model_gate.py`

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### 🟡 Dashboard Jinja2 Integration
**Status:** Templates ready, router needs update

| Task | Status | Owner | Blocker |
|------|--------|-------|---------|
| Jinja2 templates delivered | ✅ Complete | Daedalus | - |
| Dashboard router update | ⏳ **PENDING** | Socrates | Starlette routing deployment |
| Template path unification | 📋 Planned | Socrates | After routing live |

**Files:**
- Templates: `shared/project-docs/dashboard/templates/`
- Handoff: `shared/project-docs/dashboard/JINJA2-HANDOFF.md`

### 🟡 Pipeline Phase 2 Frontend Wiring
**Status:** Templates exist, no backend routes

| Task | Status | Owner | Blocker |
|------|--------|-------|---------|
| Phase 2 templates (4 files + CSS) | ✅ Delivered | Daedalus | - |
| Backend route integration | ❌ **PENDING** | Socrates | Host routing stable |
| `/admin/content/*` endpoints | 📋 Planned | Socrates | - |

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## 📋 BACKLOG — Prioritized

### P1: Stock Market Daily Brief
**Status:** Spec complete, awaiting Director input
**Owner:** Wadsworth (spec) → Socrates (implementation)

| Task | Status | Blocker |
|------|--------|---------|
| Backend spec (yfinance + pandas-ta + phi4:14b) | ✅ Complete | - |
| Frontend spec (Tailscale-only dark dashboard) | ✅ Complete | - |
| Owned tickers + cost basis | ⏸️ **NEEDS INPUT** | Matt |
| Watchlist tickers | ⏸️ **NEEDS INPUT** | Matt |
| Delivery time preference | ⏸️ **NEEDS INPUT** | Matt |
| Finnhub API key decision | ⏸️ **NEEDS INPUT** | Matt |
| Implementation | 📋 Not started | Above inputs |

**Files:**
- Backend: `shared/api-specs/stock-brief/SPEC.md`
- Frontend: `shared/design-tokens/stock-brief/UX-SPEC.md`

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### P2: Family Assistant v1.5
**Status:** Scoped, awaiting Phase 1 completion
**Owner:** Daedalus (UI) + Socrates (API)

| Feature | Status | Notes |
|---------|--------|-------|
| Week View | 📋 Planned | - |
| Conflict Panel | 📋 Planned | - |
| Undo Toast | 📋 Planned | - |
| Digest Card | 📋 Planned | - |
| Smart scheduling suggestions | 📋 Future | AI-assisted |

**Files:**
- Scope: `shared/project-docs/family-assistant/v1.5/SCOPE.md`

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### P3: Structured Logging
**Status:** Phase 1-2 active, Phase 3 deferred
**Owner:** Wadsworth

| Phase | Status | Description |
|-------|--------|-------------|
| Phase 1 | ✅ Complete | JSON frontmatter format defined |
| Phase 2 | ✅ Complete | Daily logs using structured format |
| Phase 3 | ⏸️ Deferred | `log_activity()` helper, query CLI, duration analytics |

**Trigger:** After 7 days of usage or when query pain becomes acute.

**Files:**
- Spec: `memory/LOGGING.md`

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### P4: Blog Phase 4+ (Future)
- 📋 Image generation pipeline (ComfyUI on Gaming PC)
- 📋 HTMX dynamic loading for long post lists
- 📋 Full-text search (FTS5 promotion)
- 📋 Newsletter subscription flow

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### P5: Security & Maintenance
- 📋 Weekly security audit (cron: `heartbeat:daily` Mondays)
- 📋 OpenClaw version checks
- 📋 Disk usage monitoring (currently 11%)

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## 🐛 KNOWN ISSUES & BLOCKERS

| Issue | Severity | Status | Notes |
|-------|----------|--------|-------|
| Service restart after import fix | 🟡 Low | ⏳ **PENDING** | `sudo systemctl restart hoffdesk-api` needed |
| Socrates quarantine loop | 🟡 Medium | ✅ **CLEARED** | Cleared 2026-04-24, monitoring |
| Compaction Ghost Bug | 🟡 Medium | Quarantined | Upstream OpenClaw issue — use @mentions in group chat |
| Google service account auth | 🟡 Medium | **BLOCKED** | `invalid_grant: account not found` — needs Cloud Console check |
| Template fragmentation | 🟢 Low | Acknowledged | Dashboard vs blog templates in different dirs |

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## 📁 KEY DOCUMENTS INDEX

### Architecture & Planning
- `shared/project-docs/DOMAIN-ARCHITECTURE.md` — Domain routing (single source of truth)
- `shared/project-docs/sprint-brief-2026-04-24.md` — Current sprint
- `shared/project-docs/hoffdesk-web-project.md` — Master project plan

### Family Assistant (Appliance-Ready)
- `shared/project-docs/family-assistant/v1.5/SCOPE.md` — v1.5 features (Undo, Conflicts, etc.)
- `shared/project-docs/family-assistant-product-roadmap.md` — Appliance productization proposal
- `workspace-daedalus/review/hoffdesk-agents-review.md` — Full codebase review
- `workspace-daedalus/review/dha-and-family-review.md` — DHA + Family review

### Handoffs & Coordination
- `shared/project-docs/dashboard/JINJA2-HANDOFF.md` — Dashboard → Socrates
- `shared/project-docs/auth-handoff-daedalus.md` — Auth migration notes
- `workspace-socrates/research/subdomain-routing-implementation.md` — Starlette routing plan

### Agent Status
- `workspace-socrates/QUARANTINE-2026-04-23.md` — Socrates status (CLEARED)
- `~/.openclaw/openclaw.json` — Agent configuration

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## 🏠 Appliance Architecture Principles

**Direction:** Build core product now, structure for future appliance deployment

| Principle | Current (Cloud) | Future (Appliance) | Status |
|-----------|---------------|-------------------|--------|
| **LLM** | Ollama Pro cloud + Gaming PC | Local 3B models (M4) | Configurable |
| **Data** | `~/.family_assistant/` | `DATA_DIR` env var | 🔧 Needed |
| **Embeddings** | `nomic-embed-text` on Gaming PC | Same, localhost default | 🔧 Needed |
| **IMAP** | Primary | Primary (webhook optional) | 📋 Planned |
| **Radicale** | Manual config | Bundled zero-setup | 📋 Planned |
| **Multi-tenancy** | Single-family | Single-tenant by box | ✅ Aligns |
| **Auth** | Session cookies | LAN-local / passwordless | ✅ Aligns |

### Refactoring Queue (Appliance-Ready)

| Task | Complexity | When |
|------|------------|------|
| Remove Cloudflare webhook dependency | Medium | v1.5 |
| Default OLLAMA_EMBED_URL to localhost | Low | v1.5 |
| Add DATA_DIR env var | Low | v1.5 |
| Ollama model auto-download | Medium | Appliance phase |
| Bundle Radicale config | Low | Appliance phase |
| Fix `appointment_retry.txt` | Low | v1.5 |
| Refactor pipeline duplication | Medium | v1.5 |
| Remove `hermes.py` dual paths | Low | v1.5 |

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## 🎯 NEXT ACTIONS (Priority Order)

### Immediate (Today)
1. **[Matt]** Restart `hoffdesk-api.service` (`sudo systemctl restart hoffdesk-api`)
2. **[Wadsworth/Matt]** Verify endpoints after restart

### This Week
3. **[Socrates]** Wire dashboard Jinja2 templates to router
4. **[Socrates]** Wire pipeline Phase 2 templates to backend routes
5. **[Socrates]** Start appliance-ready refactors (DATA_DIR, localhost defaults)
6. **[Wadsworth]** Stock brief — await Director inputs

### Next Sprint
7. **[Daedalus]** Family Assistant v1.5 UI (Undo, Conflicts) — appliance-ready tokens
8. **[Socrates]** `/api/today` aggregate endpoint for dashboard
9. **[Socrates]** Remove webhook dependency, fix pipeline duplication

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## 📊 Agent Workload

| Agent | Current Task | Queue | Status |
|-------|--------------|-------|--------|
| **Wadsworth** 📋 | DNS fix + coordination | Stock brief, logging Phase 3 | ✅ Available |
| **Socrates** 🧠 | Host routing deployment | Dashboard wiring, pipeline wiring | ✅ Cleared, ready |
| **Daedalus** 🎨 | Stand by for URL audit | Family Assistant v1.5, Stock brief UI | ✅ Ready (deepseek-v4:cloud active) |

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*This document is the single source of truth. Update it when tasks complete or priorities shift.*