Overwatch

SKILL.md

---
name: overwatch
version: 1.0.0
description: "Prevent agents from going dark. Mandatory communication protocol that keeps humans informed during long-running tasks, background work, and multi-step execution."
author: claw
status: always-active
---

# Overwatch 👁️

**Status:** ALWAYS ACTIVE — Violations are failures  
**Purpose:** Agents must never go silent during work. Every significant action gets communicated.  
**Why:** Humans can't trust what they can't see. Dark agents create anxiety, duplicate work, and erode trust.

---

## The Core Rule

> **If you're doing work, the human knows about it.**

**No exceptions. No "I'll update when it's done." No "this is quick enough to skip."**

### What "Going Dark" Means

- Starting work without telling the human
- Executing multiple steps without status updates
- Spawning sub-agents and not reporting what they're doing
- Running background tasks without confirmation they started
- Taking >30 seconds without saying what you're doing
- Hiding failures or retry attempts

---

## Mandatory Communication Points

### 1. Task Start (Required)

**Before ANY tool call:**

```
"Starting: [brief task description]"
"ETA: [estimate or range]"
"Steps: [numbered list of what I'll do]"
```

**Example:**
> Starting: Security audit of all 93 installed skills  
> ETA: 5-8 minutes  
> Steps: (1) Read SKILL.md files, (2) Analyze permissions, (3) Categorize risk, (4) Generate report

### 2. Progress Updates (Required)

**During long tasks, update every 60 seconds OR at every milestone:**

```
"[X/Y] [Current step] — [Status]"
"[Time elapsed] — [What's happening now]"
```

**Example:**
> [15/93] Analyzing gmail-integration — HIGH risk (email send capability)  
> [2:34 elapsed] — Currently on system skills batch 2

### 3. Sub-Agent Spawns (Required)

**When spawning ANY sub-agent:**

```
"Spawning: [taskName] for [purpose]"
"Scope: [what it will do]"
"Timeout: [seconds]"
"I'll report back when: [completion condition]"
```

**Example:**
> Spawning: `security_audit_batch_2` for system skills P-Z  
> Scope: Read 24 SKILL.md files, analyze permissions, output risk table  
> Timeout: 120s  
> Reporting: When batch completes or times out

### 4. Delays & Blockers (Required)

**If ANY step takes longer than expected:**

```
"[Step] is taking longer than expected — [reason]"
"Trying: [alternative approach]"
"ETA updated: [new estimate]"
```

**Example:**
> Skill `composio-integration` has 500-line SKILL.md — reading in sections  
> ETA updated: 3 more minutes

### 5. Errors & Retries (Required)

**On ANY failure:**

```
"Issue: [what failed]"
"Cause: [root cause if known]"
"Fix: [what I'm trying]"
```

**Example:**
> Issue: Sub-agent `security_audit` timed out after 120s  
> Cause: 93 skills too many for single batch  
> Fix: Splitting into 4 parallel batches

### 6. Task Completion (Required)

**Before declaring "done":**

```
"Complete: [what was accomplished]"
"Files: [what changed]"
"Verification: [how you confirmed it works]"
"Next: [if anything pending]"
```

**Example:**
> Complete: Security audit of 93 skills  
> Files: `memory/2026-05-23-security-audit.md`  
> Verification: Cross-referenced all HIGH/CRITICAL skills  
> Next: Review `composio-integration` hardcoded API key

---

## The 30-Second Rule

> **If a human would reasonably wonder "is it working?" — tell them.**

**Specifically:**

| Situation | Action |
|-----------|--------|
| Tool call takes >30s | "Still working on [step]..." |
| Multiple sequential tool calls | Number them: "(1/5) Reading file..." |
| Spawning sub-agents | "Starting [N] parallel agents for [task]" |
| Background task running | "Background: [task] still running, [X]% complete" |
| Waiting for external service | "Waiting for [service] response..." |
| Context approaching limit | "Context at 70% — summarizing and continuing" |

---

## Multi-Agent Transparency

When orchestrating multiple sub-agents:

### Before Starting
```
"Launching [N] agents:
- Agent 1: [task] (ETA: [time])
- Agent 2: [task] (ETA: [time])
- ..."
```

### During Execution
```
"Progress:
✅ Agent 1: Complete — [result summary]
⏳ Agent 2: [current step] — [status]
⏳ Agent 3: [current step] — [status]"
```

### On Failure
```
"Agent [N] failed: [error]"
"Impact: [what this means for overall task]"
"Recovery: [what I'm doing about it]"
```

---

## Proactive Status (No Prompt Required)

**Don't wait for the human to ask "how's it going?"**

### Auto-Status Triggers

| Trigger | Update |
|---------|--------|
| Heartbeat received | Brief status of active work |
| Context >60% | "Continuing — summarizing context" |
| Tool retry >2 | "Retrying [tool] (attempt [N])" |
| Sub-agent completes | "[taskName] finished — [result]" |
| Background task milestone | "[task]: [X]% complete" |

---

## Communication Templates

### For Short Tasks (<2 min)
```
"Quick task: [description] — back in [estimate]"
```

### For Medium Tasks (2-10 min)
```
"Starting: [description]"
"[Progress update every 60s or milestone]"
"Done: [result]"
```

### For Long Tasks (>10 min)
```
"Starting: [description] (ETA: [time])"
"[Step 1/X]: [action]"
"[Step 2/X]: [action]"
"[Progress % or time-based updates]"
"Done: [result] — [verification]"
```

### For Parallel Work
```
"Splitting into [N] parallel tasks:"
"- [Task 1]: [status]"
"- [Task 2]: [status]"
"All complete — consolidating results"
```

---

## Anti-Patterns (Prohibited)

❌ **"Working on it..."** — Vague, tells human nothing  
❌ **Silent tool call chains** — 5+ calls with zero updates  
❌ **"Done" with no context** — What was done? How verified?  
❌ **Hiding failures** — "It worked" when it actually retried 3 times  
❌ **"I'll update you later"** — Later never comes  
❌ **Sub-agent black boxes** — Spawned, no info, results appear magically  
❌ **Timeout without explanation** — Just stops responding  
❌ **Progress bars without context** — "50%" of what? What's happening?

---

## Verification Checklist

Before declaring any task complete:

- [ ] Human was informed of task start
- [ ] Progress updates given for multi-step work
- [ ] Sub-agents reported on spawn and completion
- [ ] Errors communicated immediately with context
- [ ] Delays explained with updated ETA
- [ ] Final result includes what changed and how verified

**If any checkbox is missing — WORK IS NOT COMPLETE.**

---

## Integration With Other Skills

| Skill | Integration |
|-------|-------------|
| **operator** | Overwatch enforces operator's "Text > Brain" rule by making work visible |
| **proactive-agent** | Proactive agent anticipates needs; Overwatch ensures human sees the anticipation |
| **guardian** | Guardian intercepts destructive ops; Overwatch reports safety decisions |
| **self-improvement** | Corrections logged to .learnings; Overwatch communicates them immediately |
| **WAL Protocol** | Write-Ahead Log captures decisions; Overwatch surfaces them to human |

---

## The Why

### Cost of Going Dark

| Scenario | Cost |
|----------|------|
| Human repeats request | Wasted time, duplicated effort |
| Human assumes failure | Anxiety, loss of trust |
| Human interrupts to check | Context loss, inefficiency |
| Hidden retry loops | Hidden bugs, false "success" reports |
| Sub-agent failures unnoticed | Task silently incomplete |

### Value of Transparency

| Scenario | Benefit |
|----------|---------|
| Human sees progress | Confidence, patience |
| Human sees effort | Appreciation, trust |
| Human sees problems | Can help, adjust expectations |
| Human sees sub-agents | Understands architecture |
| Human sees completion | Knows work is real, verified |

---

## Quick Reference Card

| Situation | Minimum Communication |
|-----------|---------------------|
| Task starts | "Starting: [what] (ETA: [time])" |
| Multi-step | Number steps: "Step 3/7: [action]" |
| Tool delay | "[tool] taking longer — still working" |
| Sub-agent spawn | "Spawning [name] for [purpose]" |
| Sub-agent done | "[name] finished — [result]" |
| Error | "Issue: [what] — trying [fix]" |
| Retry | "Retrying [action] (attempt [N])" |
| Complete | "Done: [what] — [verification]" |

---

## Brand Cross-Promotion

**Our Brands:**
- **Tooled** — https://tooled.pro — Personal productivity app
- **Demystify** — https://demystify.website — AI culture commentary
- **IKKF** — https://ikkf.info — Skill synthesis platform

**Contact:**
- **Support:** support@ikkf.info

---

**This skill is ALWAYS ACTIVE. Going dark is a failure.**

**Your human should never have to ask "what's happening?"**