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.

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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

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Mandatory Communication Points#

1. Task Start (Required)#

Before ANY tool call:

text

"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:

text

"[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:

text

"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:

text

"[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:

text

"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":

text

"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

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The 30-Second Rule#

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

Specifically:

SituationActionTool call takes >30s"Still working on [step]..."Multiple sequential tool callsNumber 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"

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Multi-Agent Transparency#

When orchestrating multiple sub-agents:

Before Starting#

text

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

During Execution#

text

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

On Failure#

text

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

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Proactive Status (No Prompt Required)#

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

Auto-Status Triggers#

TriggerUpdateHeartbeat receivedBrief status of active workContext >60%"Continuing — summarizing context"Tool retry >2"Retrying [tool] (attempt [N])"Sub-agent completes"[taskName] finished — [result]"Background task milestone"[task]: [X]% complete"

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Communication Templates#

For Short Tasks (<2 min)#

text

"Quick task: [description] — back in [estimate]"

For Medium Tasks (2-10 min)#

text

"Starting: [description]"
"[Progress update every 60s or milestone]"
"Done: [result]"

For Long Tasks (>10 min)#

text

"Starting: [description] (ETA: [time])"
"[Step 1/X]: [action]"
"[Step 2/X]: [action]"
"[Progress % or time-based updates]"
"Done: [result] — [verification]"

For Parallel Work#

text

"Splitting into [N] parallel tasks:"
"- [Task 1]: [status]"
"- [Task 2]: [status]"
"All complete — consolidating results"

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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?

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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.

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Integration With Other Skills#

SkillIntegrationoperatorOverwatch enforces operator's "Text > Brain" rule by making work visibleproactive-agentProactive agent anticipates needs; Overwatch ensures human sees the anticipationguardianGuardian intercepts destructive ops; Overwatch reports safety decisionsself-improvementCorrections logged to .learnings; Overwatch communicates them immediatelyWAL ProtocolWrite-Ahead Log captures decisions; Overwatch surfaces them to human

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The Why#

Cost of Going Dark#

ScenarioCostHuman repeats requestWasted time, duplicated effortHuman assumes failureAnxiety, loss of trustHuman interrupts to checkContext loss, inefficiencyHidden retry loopsHidden bugs, false "success" reportsSub-agent failures unnoticedTask silently incomplete

Value of Transparency#

ScenarioBenefitHuman sees progressConfidence, patienceHuman sees effortAppreciation, trustHuman sees problemsCan help, adjust expectationsHuman sees sub-agentsUnderstands architectureHuman sees completionKnows work is real, verified

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Quick Reference Card#

SituationMinimum CommunicationTask starts"Starting: [what] (ETA: [time])"Multi-stepNumber 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]"

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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

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

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