docs: create milestone v1.1 roadmap (4 phases)
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.planning/MILESTONES.md
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.planning/MILESTONES.md
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# Milestones
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## v1.0 MVP — Shipped 2026-06-14
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**Phases:** 4 — Hermes Install & Provider Setup, Memory/Git/Sessions, Telegram Gateway, Skills & Integrations
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**Requirements:** 22/22 complete
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**Key outcome:** Platform engineering agent with Docker isolation, Bedrock + OpenRouter, Telegram gateway, 4 custom skills
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## v1.1 Session Lifecycle, Memory & Reporting — In Planning
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**Phases:** Starting at Phase 5 (continued numbering)
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**Requirements:** MEM-01, REPO-01, REPO-02, SKIL-04, CRON-01, CRON-02, CRON-03
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**Target:** Productionize session workspace, persistent memory, operational reporting
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| Requirement | Phase | Status |
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|-------------|-------|--------|
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| MEM-01 | TBD | Pending |
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| REPO-01 | TBD | Pending |
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| REPO-02 | TBD | Pending |
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| SKIL-04 | TBD | Pending |
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| CRON-01 | TBD | Pending |
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| CRON-02 | TBD | Pending |
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| CRON-03 | TBD | Pending |
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| MEM-01 | Phase 5 | Pending |
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| REPO-01 | Phase 6 | Pending |
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| REPO-02 | Phase 6 | Pending |
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| SKIL-04 | Phase 7 | Pending |
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| CRON-01 | Phase 8 | Pending |
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| CRON-02 | Phase 8 | Pending |
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| CRON-03 | Phase 8 | Pending |
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---
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## Milestones
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- ✅ **v1.0 MVP** — Phases 1-4 (shipped 2026-06-14)
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- 🚧 **v1.1 Session Lifecycle, Memory & Reporting** — Phases 5-8 (in planning)
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## Phases
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</details>
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### 🚧 v1.1 Session Lifecycle, Memory & Reporting (In Planning)
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**Milestone Goal:** Productionize session workspace with default repos, upgrade to persistent cross-session memory (hindsight), and operationalize daily reporting with session lifecycle management.
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- [ ] **Phase 5: Hindsight Memory Provider** — Enable cross-session persistent memory with entity-aware recall via Hindsight Cloud API
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- [ ] **Phase 6: Default Repos & SSH Mount** — Auto-clone DEFAULT_REPOS into every new session with secure credential mounting
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- [ ] **Phase 7: Main Session Skill** — Session lifecycle orchestration skill covering init-to-close workflow
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- [ ] **Phase 8: Cron Reporting** — Daily session summaries, stale session archiving, and Jira integration
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## Phase Details
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### Phase 5: Hindsight Memory Provider
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**Goal**: Cross-session persistent memory with entity-aware recall via Hindsight Cloud API
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**Depends on**: Nothing (independent config change)
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**Requirements**: MEM-01
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**Success Criteria** (what must be TRUE):
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1. Agent recalls facts across sessions without user prompting (cross-session semantic recall)
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2. Agent detects similar previous sessions via hindsight similarity search on session start
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3. Memory provider is set to `hindsight` (verifiable in config and agent state)
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4. No memory provider conflicts — only one external provider registered (Hindsight, not MEMORY.md+user)
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**Plans**: TBD
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### Phase 6: Default Repos & SSH Mount
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**Goal**: Default repos auto-cloned into every new session with secure credential mounting for git operations
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**Depends on**: Nothing (independent from Phase 5)
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**Requirements**: REPO-01, REPO-02
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**Success Criteria** (what must be TRUE):
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1. New Hermes session has DEFAULT_REPOS (`rai-ops`, `rai-deployment`, `rai-devtools`) available at `/workspace/repos/`
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2. Container restart doesn't lose cloned repos (host-mounted volume persists across container lifecycle)
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3. User can request additional repo cloning mid-session and agent clones it via git command in Docker
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4. SSH credentials are mounted read-only inside Docker (verified by container inspection)
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5. Session init script completes within 30s timeout and doesn't block agent startup
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**Plans**: TBD
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### Phase 7: Main Session Skill
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**Goal**: Full session lifecycle orchestration skill covering the `initial-plan.md` workflow — init to close
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**Depends on**: Phase 5 (hindsight for session similarity detection), Phase 6 (repos in workspace)
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**Requirements**: SKIL-04
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**Success Criteria** (what must be TRUE):
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1. Agent detects similar previous sessions via hindsight on session start
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2. Agent loads DEFAULT_REPOS into workspace on session init
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3. Agent creates a Jira ticket for the session task automatically
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4. Agent loads relevant Confluence docs for context
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5. Agent updates docs and Jira ticket at session end with results summary
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**Plans**: TBD
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### Phase 8: Cron Reporting
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**Goal**: Daily operational reporting with stale session archiving and Jira integration
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**Depends on**: Phase 7 (needs SKIL-04 session lifecycle to produce meaningful sessions to report/archive)
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**Requirements**: CRON-01, CRON-02, CRON-03
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**Success Criteria** (what must be TRUE):
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1. Telegram receives daily session summary report at 09:00
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2. Daily report lists active sessions, last activity, token usage
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3. Daily report includes Jira ticket status for active sessions via ngn-jira skill
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4. Sessions inactive >30d are archived to JSON with no data loss (export-before-delete verified)
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5. Archive script supports dry-run mode for safe initial testing before activating cron
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**Plans**: TBD
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## Progress
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| Phase | Milestone | Status | Completed |
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|-------|-----------|--------|-----------|
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| 1. Hermes Install & Provider Setup | v1.0 | Complete | 2026-06-14 |
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| 2. Memory, Git & Session Management | v1.0 | Complete | 2026-06-14 |
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| 3. Telegram Gateway | v1.0 | Complete | 2026-06-14 |
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| 4. Skills & Integrations | v1.0 | Complete | 2026-06-14 |
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| Phase | Milestone | Plans Complete | Status | Completed |
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|-------|-----------|----------------|--------|-----------|
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| 1. Hermes Install & Provider Setup | v1.0 | — | Complete | 2026-06-14 |
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| 2. Memory, Git & Session Management | v1.0 | — | Complete | 2026-06-14 |
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| 3. Telegram Gateway | v1.0 | — | Complete | 2026-06-14 |
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| 4. Skills & Integrations | v1.0 | — | Complete | 2026-06-14 |
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| 5. Hindsight Memory Provider | v1.1 | 0/TBD | Not started | - |
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| 6. Default Repos & SSH Mount | v1.1 | 0/TBD | Not started | - |
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| 7. Main Session Skill | v1.1 | 0/TBD | Not started | - |
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| 8. Cron Reporting | v1.1 | 0/TBD | Not started | - |
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@@ -1,12 +1,12 @@
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---
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gsd_state_version: 1.0
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gsd_state_version: '1.0'
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milestone: v1.1
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milestone_name: Session Lifecycle, Memory & Reporting
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status: planning
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last_updated: "2026-06-14T05:46:37.415Z"
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last_activity: 2026-06-14
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last_updated: "2026-06-14T12:00:00.000Z"
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last_activity: 2026-06-14 — Milestone v1.1 roadmap created
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progress:
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total_phases: 0
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total_phases: 4
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completed_phases: 0
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total_plans: 0
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completed_plans: 0
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@@ -20,33 +20,53 @@ progress:
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See: .planning/PROJECT.md (updated 2026-06-14)
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**Core value:** Agent must NEVER mutate real infrastructure beyond what the limited IAM role permits
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**Current focus:** Phase 4 — Skills & Integrations (final phase)
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## State
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- **Status**: Phase 1-3 complete, Phase 4 skills created
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- **Current phase**: Phase 4 (Jira API token pending user setup)
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- **Last action**: Created custom skills (aws-diagnostics, jira-query, confluence-search, bitbucket-pr)
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- **Next action**: User sets JIRA_API_TOKEN, then all 22 requirements are met
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## What's Running
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- Hermes v0.16.0 CLI (Bedrock + OpenRouter fallback)
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- Telegram gateway (launchd service, PID in logs)
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- Docker terminal backend (config + SSO cache mounted)
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- 4 custom ngn-agent skills registered
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## Notes
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- .aws/config: mounted ro, SSO cache: mounted rw
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- ngn-* scripts at ~/.hermes/scripts/ mounted to /usr/local/bin:ro in Docker
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- JIRA_EMAIL and JIRA_API_TOKEN forwarded into Docker via docker_forward_env
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- Telegram paired user 474440517 (Bapung)
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- Research docs: 7 files in .planning/research/hermes/
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**Current focus:** Phase 5 — Hindsight Memory Provider (v1.1)
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## Current Position
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Phase: Not started (defining requirements)
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Plan: —
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Status: Defining requirements
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Last activity: 2026-06-14 — Milestone v1.1 started
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Phase: 5 of 8 (Hindsight Memory Provider)
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Plan: — (not yet planned)
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Status: Not started — roadmap defined, ready to plan
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Last activity: 2026-06-14 — Milestone v1.1 roadmap created
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Progress: [░░░░░░░░░░] 0%
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## Performance Metrics
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**Velocity:**
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- Total plans completed: 0
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- Average duration: — min
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- Total execution time: 0.0 hours
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**By Phase:**
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| Phase | Plans | Total | Avg/Plan |
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|-------|-------|-------|----------|
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| — | — | — | — |
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**Recent Trend:**
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- Last 5 plans: —
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- Trend: —
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## Accumulated Context
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### Decisions
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Decisions are logged in PROJECT.md Key Decisions table.
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- (v1.1 planning): Phase numbering continues from v1.0 (starts at Phase 5)
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- (v1.1 planning): 4 phases with coarse granularity — Hindsight, Repos, Session Skill, Cron
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### Pending Todos
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None yet.
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### Blockers/Concerns
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None yet.
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## Session Continuity
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Last session: 2026-06-14
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Stopped at: Milestone v1.1 roadmap created
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Resume file: None
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