docs: create milestone v1.1 roadmap (4 phases)

.planning/MILESTONES.md

@@ -0,0 +1,13 @@
+# Milestones
+
+## v1.0 MVP — Shipped 2026-06-14
+
+**Phases:** 4 — Hermes Install & Provider Setup, Memory/Git/Sessions, Telegram Gateway, Skills & Integrations
+**Requirements:** 22/22 complete
+**Key outcome:** Platform engineering agent with Docker isolation, Bedrock + OpenRouter, Telegram gateway, 4 custom skills
+
+## v1.1 Session Lifecycle, Memory & Reporting — In Planning
+
+**Phases:** Starting at Phase 5 (continued numbering)
+**Requirements:** MEM-01, REPO-01, REPO-02, SKIL-04, CRON-01, CRON-02, CRON-03
+**Target:** Productionize session workspace, persistent memory, operational reporting

.planning/REQUIREMENTS.md

@@ -57,13 +57,13 @@
 
 | Requirement | Phase | Status |
 |-------------|-------|--------|
-| MEM-01 | TBD | Pending |
+| MEM-01 | Phase 5 | Pending |
-| REPO-01 | TBD | Pending |
+| REPO-01 | Phase 6 | Pending |
-| REPO-02 | TBD | Pending |
+| REPO-02 | Phase 6 | Pending |
-| SKIL-04 | TBD | Pending |
+| SKIL-04 | Phase 7 | Pending |
-| CRON-01 | TBD | Pending |
+| CRON-01 | Phase 8 | Pending |
-| CRON-02 | TBD | Pending |
+| CRON-02 | Phase 8 | Pending |
-| CRON-03 | TBD | Pending |
+| CRON-03 | Phase 8 | Pending |
 
 ---
 

.planning/ROADMAP.md

@@ -3,6 +3,7 @@
 ## Milestones
 
 - ✅ **v1.0 MVP** — Phases 1-4 (shipped 2026-06-14)
+- 🚧 **v1.1 Session Lifecycle, Memory & Reporting** — Phases 5-8 (in planning)
 
 ## Phases
 
@@ -16,11 +17,73 @@
 
 </details>
 
+### 🚧 v1.1 Session Lifecycle, Memory & Reporting (In Planning)
+
+**Milestone Goal:** Productionize session workspace with default repos, upgrade to persistent cross-session memory (hindsight), and operationalize daily reporting with session lifecycle management.
+
+- [ ] **Phase 5: Hindsight Memory Provider** — Enable cross-session persistent memory with entity-aware recall via Hindsight Cloud API
+- [ ] **Phase 6: Default Repos & SSH Mount** — Auto-clone DEFAULT_REPOS into every new session with secure credential mounting
+- [ ] **Phase 7: Main Session Skill** — Session lifecycle orchestration skill covering init-to-close workflow
+- [ ] **Phase 8: Cron Reporting** — Daily session summaries, stale session archiving, and Jira integration
+
+## Phase Details
+
+### Phase 5: Hindsight Memory Provider
+**Goal**: Cross-session persistent memory with entity-aware recall via Hindsight Cloud API
+**Depends on**: Nothing (independent config change)
+**Requirements**: MEM-01
+**Success Criteria** (what must be TRUE):
+  1. Agent recalls facts across sessions without user prompting (cross-session semantic recall)
+  2. Agent detects similar previous sessions via hindsight similarity search on session start
+  3. Memory provider is set to `hindsight` (verifiable in config and agent state)
+  4. No memory provider conflicts — only one external provider registered (Hindsight, not MEMORY.md+user)
+**Plans**: TBD
+
+### Phase 6: Default Repos & SSH Mount
+**Goal**: Default repos auto-cloned into every new session with secure credential mounting for git operations
+**Depends on**: Nothing (independent from Phase 5)
+**Requirements**: REPO-01, REPO-02
+**Success Criteria** (what must be TRUE):
+  1. New Hermes session has DEFAULT_REPOS (`rai-ops`, `rai-deployment`, `rai-devtools`) available at `/workspace/repos/`
+  2. Container restart doesn't lose cloned repos (host-mounted volume persists across container lifecycle)
+  3. User can request additional repo cloning mid-session and agent clones it via git command in Docker
+  4. SSH credentials are mounted read-only inside Docker (verified by container inspection)
+  5. Session init script completes within 30s timeout and doesn't block agent startup
+**Plans**: TBD
+
+### Phase 7: Main Session Skill
+**Goal**: Full session lifecycle orchestration skill covering the `initial-plan.md` workflow — init to close
+**Depends on**: Phase 5 (hindsight for session similarity detection), Phase 6 (repos in workspace)
+**Requirements**: SKIL-04
+**Success Criteria** (what must be TRUE):
+  1. Agent detects similar previous sessions via hindsight on session start
+  2. Agent loads DEFAULT_REPOS into workspace on session init
+  3. Agent creates a Jira ticket for the session task automatically
+  4. Agent loads relevant Confluence docs for context
+  5. Agent updates docs and Jira ticket at session end with results summary
+**Plans**: TBD
+
+### Phase 8: Cron Reporting
+**Goal**: Daily operational reporting with stale session archiving and Jira integration
+**Depends on**: Phase 7 (needs SKIL-04 session lifecycle to produce meaningful sessions to report/archive)
+**Requirements**: CRON-01, CRON-02, CRON-03
+**Success Criteria** (what must be TRUE):
+  1. Telegram receives daily session summary report at 09:00
+  2. Daily report lists active sessions, last activity, token usage
+  3. Daily report includes Jira ticket status for active sessions via ngn-jira skill
+  4. Sessions inactive >30d are archived to JSON with no data loss (export-before-delete verified)
+  5. Archive script supports dry-run mode for safe initial testing before activating cron
+**Plans**: TBD
+
 ## Progress
 
-| Phase | Milestone | Status | Completed |
+| Phase | Milestone | Plans Complete | Status | Completed |
-|-------|-----------|--------|-----------|
+|-------|-----------|----------------|--------|-----------|
-| 1. Hermes Install & Provider Setup | v1.0 | Complete | 2026-06-14 |
+| 1. Hermes Install & Provider Setup | v1.0 | — | Complete | 2026-06-14 |
-| 2. Memory, Git & Session Management | v1.0 | Complete | 2026-06-14 |
+| 2. Memory, Git & Session Management | v1.0 | — | Complete | 2026-06-14 |
-| 3. Telegram Gateway | v1.0 | Complete | 2026-06-14 |
+| 3. Telegram Gateway | v1.0 | — | Complete | 2026-06-14 |
-| 4. Skills & Integrations | v1.0 | Complete | 2026-06-14 |
+| 4. Skills & Integrations | v1.0 | — | Complete | 2026-06-14 |
+| 5. Hindsight Memory Provider | v1.1 | 0/TBD | Not started | - |
+| 6. Default Repos & SSH Mount | v1.1 | 0/TBD | Not started | - |
+| 7. Main Session Skill | v1.1 | 0/TBD | Not started | - |
+| 8. Cron Reporting | v1.1 | 0/TBD | Not started | - |

.planning/STATE.md

@@ -1,12 +1,12 @@
 ---
-gsd_state_version: 1.0
+gsd_state_version: '1.0'
 milestone: v1.1
 milestone_name: Session Lifecycle, Memory & Reporting
 status: planning
-last_updated: "2026-06-14T05:46:37.415Z"
+last_updated: "2026-06-14T12:00:00.000Z"
-last_activity: 2026-06-14
+last_activity: 2026-06-14 — Milestone v1.1 roadmap created
 progress:
-  total_phases: 0
+  total_phases: 4
   completed_phases: 0
   total_plans: 0
   completed_plans: 0
@@ -20,33 +20,53 @@ progress:
 See: .planning/PROJECT.md (updated 2026-06-14)
 
 **Core value:** Agent must NEVER mutate real infrastructure beyond what the limited IAM role permits
-**Current focus:** Phase 4 — Skills & Integrations (final phase)
+**Current focus:** Phase 5 — Hindsight Memory Provider (v1.1)
-
-## State
-
-- **Status**: Phase 1-3 complete, Phase 4 skills created
-- **Current phase**: Phase 4 (Jira API token pending user setup)
-- **Last action**: Created custom skills (aws-diagnostics, jira-query, confluence-search, bitbucket-pr)
-- **Next action**: User sets JIRA_API_TOKEN, then all 22 requirements are met
-
-## What's Running
-
-- Hermes v0.16.0 CLI (Bedrock + OpenRouter fallback)
-- Telegram gateway (launchd service, PID in logs)
-- Docker terminal backend (config + SSO cache mounted)
-- 4 custom ngn-agent skills registered
-
-## Notes
-
-- .aws/config: mounted ro, SSO cache: mounted rw
-- ngn-* scripts at ~/.hermes/scripts/ mounted to /usr/local/bin:ro in Docker
-- JIRA_EMAIL and JIRA_API_TOKEN forwarded into Docker via docker_forward_env
-- Telegram paired user 474440517 (Bapung)
-- Research docs: 7 files in .planning/research/hermes/
 
 ## Current Position
 
-Phase: Not started (defining requirements)
+Phase: 5 of 8 (Hindsight Memory Provider)
-Plan: —
+Plan: — (not yet planned)
-Status: Defining requirements
+Status: Not started — roadmap defined, ready to plan
-Last activity: 2026-06-14 — Milestone v1.1 started
+Last activity: 2026-06-14 — Milestone v1.1 roadmap created
+
+Progress: [░░░░░░░░░░] 0%
+
+## Performance Metrics
+
+**Velocity:**
+- Total plans completed: 0
+- Average duration: — min
+- Total execution time: 0.0 hours
+
+**By Phase:**
+
+| Phase | Plans | Total | Avg/Plan |
+|-------|-------|-------|----------|
+| — | — | — | — |
+
+**Recent Trend:**
+- Last 5 plans: —
+- Trend: —
+
+## Accumulated Context
+
+### Decisions
+
+Decisions are logged in PROJECT.md Key Decisions table.
+
+- (v1.1 planning): Phase numbering continues from v1.0 (starts at Phase 5)
+- (v1.1 planning): 4 phases with coarse granularity — Hindsight, Repos, Session Skill, Cron
+
+### Pending Todos
+
+None yet.
+
+### Blockers/Concerns
+
+None yet.
+
+## Session Continuity
+
+Last session: 2026-06-14
+Stopped at: Milestone v1.1 roadmap created
+Resume file: None