Shadman's AI Operating System: Architecture Map v3

01 · Data Sources

Granola

Meeting transcripts, summaries, action items

every 15 min

→ trace flow

Reads into

Obsidian vault via granola-obsidian-sync. Also fan-out to _scratch/granola/ staging by granola_ingest.sh

Confluence

Work wiki, team docs, project pages

hourly weekdays

→ trace flow

Reads into

Obsidian vault via confluence-obsidian-sync. Used as RAG source by ask/recall router intent.

M365

Outlook calendar, email, Teams messages

06:30 + pre-cache 3x

→ trace flow

Cache written to

_work/pm-workspace/.cache/calendar-YYYY-MM-DD.json. Read by morning digest + midday ping.

GitHub

PRs, CI status, work tickets, review requests

via Kit 16:00

→ trace flow

Fetched by

kit_github_pulse.sh via gh CLI. Work repos + SSO auth. Sonnet synthesis, terse Telegram output.

Jira / TWG

Work queue, sprint tickets, backlog items

08:25 pre-digest

→ trace flow

Cache written to

_work/pm-workspace/.cache/queue-YYYY-MM-DD.json. Read by morning digest + midday ping.

GA4: CCG

claudecodeguide.dev traffic, page stats

Sun 07:30

→ trace flow

Snapshot written to

_tools/ccg-analytics/snapshots/. Read by nusaybah_outbound_pulse.sh on Mon + Thu.

GA4: PrintPick

printpick.dev traffic + affiliate conversions

Sun 07:35

→ trace flow

Snapshot written to

_tools/printpick-analytics/snapshots/. Nusaybah reads for side project revenue tracking.

Ad Server

Ad flight performance, campaign visibility, CTR

08:00 daily

→ trace flow

Output

Ad server pulse.py queries API, writes JSON. Used for work context only.

Daily Inbox

_scratch/inbox/YYYY-MM-DD.md
Telegram messages from @ShadmansRootBot written here by inbox_listener.sh

every 1 min

→ trace flow

Written by

nabila_inbox_listener.sh (crontab). Polled by nabila_router LaunchAgent every 60s for new entries.

Work Wiki

Confluence clone for RAG and work corpus

23:00 nightly

→ trace flow

Written to

_reference/library/work-corpus/ via wiki_ingest.sh + work_corpus_sync.sh. Used as RAG by ask intent.

01b · Real-Time Router (Nabila)

nabila_router.sh every 60s

Hashes new inbox entries, classifies intent via Haiku, routes to handler

capture

recall / ask

find_time

brief_feedback

diagnose_block ✨

meta

capture → _product-brain/

Routes to project file or ideas/ fallback. Appends with topic, title, tags.

Routed to

_product-brain/PROJECT.md when Haiku matches a known project. Otherwise _scratch/content/ideas/YYYY-MM-DD-slug.md

recall → ROOT search

Sonnet queries semantic index + memory shards. URL in message = instant redirect, no 180s burn.

Uses

ROOT MCP for semantic retrieval. Sonnet model. 180s alarm timeout. URL guard: if message contains https://, skips lookup immediately and tells Shadman to ask in a live session instead. Duration log clamped to 180s ceiling to filter machine-sleep inflation from wall-clock measurements.

diagnose_block ✨ NEW

Haiku classifies block as cognitive/emotional/capability. Returns 3-line diagnosis to Telegram.

Triggers on

"stuck on", "keep avoiding", "blocked on", "can't get started". 60s timeout. Haiku model.

02 · Persona Agents

Nabila my wife

Chief of Staff · Work + PM ops

Morning DigestMon-Fri 08:30

Queue Fetch (pre-load)Mon-Fri 08:25

Calendar Fetch (cache)05:30 / 07:30 / 12:30

Midday Ping NEWMon-Fri 13:00

Meeting CoachMon-Fri 18:00

Nina Thursday NudgeThu 09:30

Nina Friday BriefFri 13:30

Nina Post-1:1 CaptureFri 16:00

Block Scan NEWMon 08:15

Reads: calendar cache · queue cache · Granola · MEMORY.md · last-1on1-outcomes

Full-day calendar synthesis with decisions and sharp questions. Midday re-rank of top closures. Monday block scan surfaces avoidance patterns before they compound. Friday 1:1 loop: Thursday gap-check surfaces open items before the brief, post-meeting capture extracts Nina's asks and commitments so next week starts with ground truth.

Nusaybah my daughter

Outbound · Revenue + Content

Outbound PulseMon 08:00 + Thu 17:00

PrintPick Drift CheckSun 09:00

Reads: GA4 (CCG + PrintPick) · GSC · Substack · LinkedIn

Moonlight traffic via GA4 + GSC, content performance across Substack and LinkedIn, affiliate revenue signal. PrintPick drift check surfaces price drops and broken links before they erode revenue. Repurposing cadence (Tincture-inspired): when a post lands well, surfaces a Day 0-3 cross-channel republishing plan in the Monday pulse.

Musa my son

Hobby · Property Mgmt App + Medical ERP

Hobby PulseWed 19:00 + Sun 19:00

Reads: _hobby/* · Property mgmt analytics · Medical ERP status

Low-pressure builder check-in. No deadlines enforced. Musa exists so hobby projects don't get swallowed by work noise.

Kit

GitHub · PR queue + CI

GitHub PulseMon-Fri 16:00

Reads: Work repos · open tickets · CI runs

End-of-day signal on PRs needing action before morning standup. Bug ticket freshness. Review requests from teammates.

03 · Memory and Knowledge Store

Hot: Always Loaded

MEMORY.md router

CLAUDE.md

session context

Under 200 lines combined. Routes to topic shards on demand.

Constraint

200-line hard limit. Anything past that is truncated by the harness. Keep the index lean.

Warm: Loaded on Demand

_index_work.md

_index_moonlight.md

_index_infra.md

_index_feedback.md

_index_people.md

267+ topic files

Load pattern

MEMORY.md router table decides which shard to load. Never load all shards. Token budget rule: max 2 files in main thread before subagent.

Semantic: ROOT Index

ROOT MCP

Obsidian vault (5min)

hourly indexer (Haiku)

vault topic index (18:15)

How it works

ROOT indexes the Obsidian vault. Vector lookup = zero LLM tokens. Used by recall intent + planned overnight block analysis.

_product-brain/

Living project files per moonlight project. Router appends captures. Morning digest reads for context.

Pattern

One .md file per project. Capture handler appends timestamped sections. Nabila morning digest reads first 6KB of each.

_context/handoffs/

Session continuity. Handoffs written after multi-step work. Last 5 surfaced in MEMORY.md router.

Aging

Full list at _context/handoffs/INDEX.md. Last 5 entries shown in MEMORY.md. Older ones searchable via ROOT.

_reference/library/

Work corpus (weekly sync), research, Confluence clone (nightly). 90-day idle sweep.

Lifecycle

Read-only. scratch_retention.sh sweeps after 90 days idle. Build artifacts stripped on clone.

04 · Governance and Health

Workspace Health

Invariant check: git, structure, soak rules, paths.

09:00 daily

Checks

26 invariants including: git clean, nested repo isolation, runtime state gitignored, LaunchAgent exit codes, cron log freshness, Telegram reachability.

Cost Dashboard

Daily quota usage across all LLM crons. Posts to Telegram.

22:00 daily

Why it matters

All 25+ agents share one Claude Max subscription. One quota blowout breaks all downstream agents until reset. Circuit breaker.

Log Alerter

Scans cron logs for FAIL signatures. Fires Telegram on first match.

every 15 min

Pattern

Reads _tools/scripts/.logs/*.log for lines containing FAIL. One alert per failure window. Stops noise on repeat failures.

Semantic Lint

LLM pass over workspace for drift, stale rules, broken refs.

1st Sun/month

Scope

Checks MEMORY.md shards, CLAUDE.md, rule files, skill definitions for internal contradictions and rot.

Skill Audit

Reviews Claude skill definitions for staleness.

Sun 08:00

Checks

47 skills in _context/skills/. Flags trigger conditions that no longer match real usage patterns.

Memory Drift

Weekly MEMORY.md re-bloat check.

Sun 21:00

Rule

MEMORY.md hard limit: 200 lines. Drift check catches entries that should graduate to topic shards per aging policy.

Weekly Actions

Sunday action doc: open commitments, new items, auto-closures from completion signals.

Sun 10:00 CEST

→ trace flow

Pipeline

Scans Obsidian Keystone/ (incl. Captures/ from Telegram). Detects completion signals. Auto-closes matched open items. Output: _work/actions/YYYY-MM-DD-week-actions.md

Open Loops

Monthly count of unresolved TODOs across topic shards.

1st of month

Source

Scans all _index_*.md files for TODOs and "open:" markers. Reports count per shard.

Scratch Retention

Per-folder sweep of _scratch/. Marks delivered files.

Sun 23:00

TTL rules

ideas/: 30d. playground/: 14d. dogfood/: 7d after report. granola/: 90d. Default DRY_RUN=1, must flip to actually delete.

Auto-Sync

Nightly backup commit across all workspace repos.

22:00 daily

Safety

mkdir mutex to prevent race with SessionEnd hook. EDEADLK guard added May 5. Gitignores: .state/, .locks/.

Zombie Scripts

Quarterly scan for cron scripts untouched 90+ days.

quarterly

Action

Reports scripts to decommission. Does not delete. Requires manual confirmation before removal.

05 · Delivery and Security

Primary surface. All 4 personas deliver to one Root Bot chat. Persona header on every message.

Nabila · Nusaybah · Musa · Kit

Constraints

Plain text only. No markdown tables. 4000-char limit per message. Long replies split with notification suppression on continuations.

Brief Archive

Every persona delivery archived to
_work/pm-workspace/briefs/

Structure

briefs/nabila/, briefs/kit/, briefs/nusaybah/, briefs/musa/. One .md file per run. Searchable history via ROOT.

Obsidian Vault

Synced every 5 min. Human-readable view of all structured knowledge. Mobile via Obsidian app.

every 5 min

Bidirectional via ROOT

workspace → Obsidian (sync). Telegram captures also write TO Obsidian Keystone/Captures/ so ROOT indexes them. ROOT feeds the weekly action scanner. The vault is the single source of truth for all indexed knowledge.

Credential Architecture

1Password (canonical)

Telegram bot · GA4 SA · Atlassian · Anthropic API

↓

bootstrap_secrets.sh

Portable restore on new Mac. Single command.

↓

~/.config/shell/secrets.env

Cron runtime. No biometric. No network.

Remote sessions: read+draft only. Never action keys.

Security boundary

Remote Claude Code sessions (web, Codex CLI) see context-snapshot mirror. Never the secrets.env file. Deliberate isolation.

Operating Principles

Four personas, one pool

Every cron belongs to exactly one persona. No "general" agents. No shared ownership.

Why

Prevents overlapping briefs, unclear ownership, and duplicate LLM calls for the same data.

7-day soak rule

No new automation until the previous one runs unattended for 7 days.

Why

Stability over velocity. New agents frequently have silent failure modes that only surface under real conditions over time.

Subagent-first

3+ files = subagent. Parallel over sequential. Main thread stays lean.

Enforced by

UserPromptSubmit hook (subagent-nudge.sh) that warns when the pattern is about to be violated.

Repos stay clean

No secrets in any repo. Runtime state gitignored. Portability lives in 1Password.

Enforced by

git_guard.py pre-commit hook. .gitignore covers .state/, .locks/, secrets.env patterns.

Ship and verify

"Shipped" = live URL + HTTP 200 + fingerprint grepped. Not "merged." Not "pushed."

Why

"Push to main" and "live for users" are not the same event. Shadman ships solo and needs confirmation to move on.