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docs: create roadmap (5 phases)

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Lucas Berger
2026-06-03 16:15:27 -04:00
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.planning/REQUIREMENTS.md
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## Traceability
Which phases cover which requirements. Populated during roadmap creation.
| Requirement | Phase | Status |
|-------------|-------|--------|
| AUTH-01 | TBD | Pending |
| AUTH-02 | TBD | Pending |
| AUTH-03 | TBD | Pending |
| CAL-01 | TBD | Pending |
| CAL-02 | TBD | Pending |
| CAL-03 | TBD | Pending |
| CAL-04 | TBD | Pending |
| CAL-05 | TBD | Pending |
| CAL-06 | TBD | Pending |
| CAL-07 | TBD | Pending |
| CAL-08 | TBD | Pending |
| LIST-01 | TBD | Pending |
| LIST-02 | TBD | Pending |
| LIST-03 | TBD | Pending |
| LIST-04 | TBD | Pending |
| NOTIF-01 | TBD | Pending |
| NOTIF-02 | TBD | Pending |
| NOTIF-03 | TBD | Pending |
| PWA-01 | TBD | Pending |
| PWA-02 | TBD | Pending |
| AUTH-01 | Phase 1 | Pending |
| AUTH-02 | Phase 1 | Pending |
| AUTH-03 | Phase 1 | Pending |
| CAL-01 | Phase 1 | Pending |
| CAL-08 | Phase 1 | Pending |
| CAL-02 | Phase 2 | Pending |
| CAL-03 | Phase 2 | Pending |
| CAL-04 | Phase 3 | Pending |
| CAL-05 | Phase 3 | Pending |
| CAL-06 | Phase 3 | Pending |
| CAL-07 | Phase 3 | Pending |
| PWA-01 | Phase 3 | Pending |
| PWA-02 | Phase 3 | Pending |
| LIST-01 | Phase 4 | Pending |
| LIST-02 | Phase 4 | Pending |
| LIST-03 | Phase 4 | Pending |
| LIST-04 | Phase 4 | Pending |
| NOTIF-01 | Phase 5 | Pending |
| NOTIF-02 | Phase 5 | Pending |
| NOTIF-03 | Phase 5 | Pending |
**Coverage:**
- v1 requirements: 20 total
- Mapped to phases: 0 (set by roadmapper)
- Unmapped: 20 ⚠️ (resolved at roadmap step)
- Mapped to phases: 20
- Unmapped: 0 ✓
---
*Requirements defined: 2026-06-03*
*Last updated: 2026-06-03 after initial definition*
*Last updated: 2026-06-03 — traceability populated by roadmapper*
.planning/ROADMAP.md
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# Roadmap: FamilySync
## Overview
FamilySync is built in five phases, each delivering an end-to-end user-observable capability. Phase 1 is both the foundation and the highest-risk gate: OIDC auth must work and the CalDAV broker must prove it can read personal Fastmail calendars before any calendar UI is built. Phases 2–3 complete the calendar. Phase 4 delivers shared lists with live co-edit sync. Phase 5 wires up Web Push notifications. The dependency chain is strict: each phase is a prerequisite for the next, except the lists track (Phase 4) which is independent of the calendar write path.
## 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 + Broker Spike** - Auth, Docker scaffold, CalDAV broker read path, and personal-calendar ACL spike (go/no-go gate)
- [ ] **Phase 2: Calendar Display** - Read-only unified color-coded calendar (week/month/day/agenda) built on the confirmed broker
- [ ] **Phase 3: Event Write-Back + PWA Install** - Full event CRUD written back to Fastmail, PWA manifest + service worker, guided iOS install flow
- [ ] **Phase 4: Shared Lists + Live Sync** - Named collaborative lists with item CRUD and real-time SSE co-edit sync
- [ ] **Phase 5: Web Push Notifications** - VAPID push for event reminders, event changes, and list-change alerts
## Phase Details
### Phase 1: Foundation + Broker Spike
**Goal**: The app stack is running, both members can authenticate, and the CalDAV broker can read Fastmail calendars — with a confirmed go/no-go decision on personal-calendar cross-account sharing
**Mode:** mvp
**Depends on**: Nothing (first phase)
**Requirements**: AUTH-01, AUTH-02, AUTH-03, CAL-01, CAL-08
**Success Criteria** (what must be TRUE):
1. Both members can reach the app URL, authenticate through Authelia OIDC, and land on the app home page without entering any Fastmail credentials
2. Sessions persist across browser restarts — neither member is asked to log in again on the next visit
3. Each member is assigned a stable, distinct display color that does not change between sessions
4. The broker successfully fetches and caches at least one event from the shared Fastmail calendar via CalDAV PROPFIND/REPORT
5. The personal-calendar ACL spike produces a documented go/no-go decision: either the broker token sees the wife's personal calendar after Fastmail share+accept, or the fallback strategy (shared-family-only or per-member app password) is chosen and recorded
**Plans**: TBD
### Phase 2: Calendar Display
**Goal**: Both members can see a unified, color-coded calendar aggregating all accessible Fastmail calendars across day, week, month, and agenda views — read-only, no write-back yet
**Mode:** mvp
**Depends on**: Phase 1
**Requirements**: CAL-02, CAL-03, CAL-07
**Success Criteria** (what must be TRUE):
1. Opening the app shows a color-coded calendar where each member's events appear in their assigned color, with shared events distinguishable from personal events
2. The user can switch between day, week, month, and agenda views and all events render correctly in each view
3. A recurring event (e.g., weekly meeting) displays all its occurrences correctly in the current view window, including correct behavior across DST boundaries
4. All-day events (birthdays, holidays) appear as full-day banners on the correct date with no timezone shift
**Plans**: TBD
**UI hint**: yes
### Phase 3: Event Write-Back + PWA Install
**Goal**: Both members can create, edit, and delete events that are written back to the correct Fastmail calendar, and the app is installable to the iPhone and Android home screens with a guided onboarding flow
**Mode:** mvp
**Depends on**: Phase 2
**Requirements**: CAL-04, CAL-05, CAL-06, CAL-07, PWA-01, PWA-02
**Success Criteria** (what must be TRUE):
1. A member can create a timed or all-day event (including recurring events) in the app and see it appear in the native Fastmail app within the next sync cycle
2. A member can edit an existing event's title, time, or description and the change persists correctly in Fastmail
3. A member can delete an event and it disappears from all views on the next sync
4. On Android, the app shows a browser install prompt and installs to the home screen; on iOS, the app shows a guided "Add to Home Screen" walkthrough with annotated screenshots that a non-technical user can follow independently
5. The installed PWA opens full-screen without browser chrome on both iOS and Android
**Plans**: TBD
**UI hint**: yes
### Phase 4: Shared Lists + Live Sync
**Goal**: Both members can create and manage shared named lists with real-time co-edit sync — edits by one member appear for the other without any manual refresh
**Mode:** mvp
**Depends on**: Phase 1
**Requirements**: LIST-01, LIST-02, LIST-03, LIST-04
**Success Criteria** (what must be TRUE):
1. Either member can create a named list (e.g., "Groceries") and delete a list they no longer need
2. Either member can add items to a list, check items off, reorder them by drag-and-drop, and delete individual items
3. When one member adds or checks off an item, the other member sees the change appear in the list within a few seconds without refreshing — even if they reconnect after a brief network gap
**Plans**: TBD
**UI hint**: yes
### Phase 5: Web Push Notifications
**Goal**: Both members receive timely Web Push alerts for upcoming events, event changes made by the other member, and list changes — reliably on both iOS and Android
**Mode:** mvp
**Depends on**: Phase 3, Phase 4
**Requirements**: NOTIF-01, NOTIF-02, NOTIF-03
**Success Criteria** (what must be TRUE):
1. A member receives a push notification on their phone approximately 15 minutes before a calendar event starts — delivered to the installed PWA, including on iOS
2. When the other member adds or changes a calendar event, the first member receives a push notification with the event title and action described in the payload
3. When the other member modifies a shared list (adds, checks off, or deletes an item), the first member receives a push notification identifying the list and the change
4. After an extended period of app inactivity, push notifications are still delivered (subscription health-check prevents silent revocation on iOS)
**Plans**: TBD
## Progress
**Execution Order:**
Phases execute in numeric order: 1 → 2 → 3 → 4 → 5
Note: Phase 4 depends only on Phase 1 and can begin as soon as Phase 1 is complete. It is serialized here to reduce work-in-progress.
| Phase | Plans Complete | Status | Completed |
|-------|----------------|--------|-----------|
| 1. Foundation + Broker Spike | 0/? | Not started | - |
| 2. Calendar Display | 0/? | Not started | - |
| 3. Event Write-Back + PWA Install | 0/? | Not started | - |
| 4. Shared Lists + Live Sync | 0/? | Not started | - |
| 5. Web Push Notifications | 0/? | Not started | - |
.planning/STATE.md
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---
gsd_state_version: '1.0'
status: planning
progress:
total_phases: 5
completed_phases: 0
total_plans: 0
completed_plans: 0
percent: 0
---
# Project State
## Project Reference
See: .planning/PROJECT.md (updated 2026-06-03)
**Core value:** One color-coded family calendar (shared + personal) and shared lists from a single low-friction PWA — cross-ecosystem, no app store
**Current focus:** Phase 1 — Foundation + Broker Spike
## Current Position
Phase: 1 of 5 (Foundation + Broker Spike)
Plan: 0 of ? in current phase
Status: Ready to plan
Last activity: 2026-06-03 — Roadmap created
Progress: [░░░░░░░░░░] 0%
## Performance Metrics
**Velocity:**
- Total plans completed: 0
- Average duration: -
- Total execution time: 0 hours
**By Phase:**
| Phase | Plans | Total | Avg/Plan |
|-------|-------|-------|----------|
| - | - | - | - |
**Recent Trend:**
- Last 5 plans: -
- Trend: -
*Updated after each plan completion*
## Accumulated Context
### Decisions
Decisions are logged in PROJECT.md Key Decisions table.
Recent decisions affecting current work:
- Phase 1 gate: Personal-calendar CalDAV ACL must be spiked before calendar UI is built. Fallback is shared-family-only if spike fails.
- CalDAV locked: Fastmail does not expose calendars over JMAP. CalDAV via tsdav is the only protocol. No reconsideration.
- Identity: Use oidc_iss + oidc_sub as stable composite key. Never email.
- Real-time transport: Prefer SSE over WebSocket (proxy-resilient through Pangolin). Verify Pangolin SSE pass-through in Phase 1 infra spike.
- Recurring events: Create + display only in v1 (CALDAV:expand on server side). Single-occurrence edit deferred to v1.x.
### Pending Todos
None yet.
### Blockers/Concerns
- Phase 1: Personal-calendar CalDAV ACL behavior on Fastmail is LOW confidence (must spike). Failure degrades unified view to shared-family-only for v1.
- Phase 1: Pangolin SSE/WebSocket pass-through is an open infra question (known issue #1034). Must smoke-test before Phase 4 real-time sync is built.
- Phase 3: iOS install guide is load-bearing for the wife — she will never receive push notifications if she does not install the PWA.
- Phase 5: iOS push subscriptions silently revoked after 3 silent pushes. Subscription health-check and event.waitUntil() are mandatory from day one.
## Deferred Items
| Category | Item | Status | Deferred At |
|----------|------|--------|-------------|
| Calendar | Single-occurrence recurring edit (RECURRENCE-ID) | v1.x | Roadmap |
| Calendar | "This and following" recurring edit | v1.x | Roadmap |
| Calendar | Apple Calendar native subscribe URL docs | v1.x | Roadmap |
| Calendar | Secondary timezone display toggle | v1.x | Roadmap |
| Display | Wall-display / kiosk dashboard | v2 | PROJECT.md |
## Session Continuity
Last session: 2026-06-03
Stopped at: Roadmap created, STATE.md initialized. Ready to plan Phase 1.
Resume file: None