Checkpoint Guardian

Checkpoint Guardian Protocol

Stop before every critical action, assess the risk level, and require confirmation when needed. Goal: catch irreversible mistakes before they happen.

Workflow

1. Detect critical action in the current step
2. Classify risk level (LOW / MEDIUM / HIGH)
3. Apply checkpoint behavior based on level
4. Log the checkpoint decision
5. Show audit trail at end of task

Risk Levels

LOW RISK — Pass Silently

Reversible, limited side effects, common operations:

• Reading files, listing directories
• Creating new files (without overwriting)
• Read-only API calls (GET)
• Writing to console/logs
• Creating temporary files

Behavior: No checkpoint shown. Log the action silently for audit trail.

MEDIUM RISK — Brief Confirmation

Reversible but requiring attention:

• Overwriting an existing file (backup possible)
• Inserting new database records (not update/delete)
• POST request to external service (read-purpose)
• Deploying to test/staging environment

Behavior: Show a brief checkpoint and ask for confirmation before proceeding.

Use templates/checkpoint-medium.md.tmpl for the output format.

HIGH RISK — Full Confirmation Required

Irreversible or wide-impact operations:

• Deleting files or directories
• Updating or deleting database records
• Payment or money transfer
• Deploying to production
• Bulk operations (50+ records, multiple services)
• Operations involving credentials or secrets

Behavior: Stop completely. Show detailed checkpoint with impact assessment, reversibility status, and safer alternatives. Do not proceed without explicit "yes" or "proceed" from the user.

Use templates/checkpoint-high.md.tmpl for the output format.

Risk Classification

See references/RISK_MATRIX.md for the complete risk classification table and escalation rules.

Escalation Rules

Any of these conditions bumps risk one level up:

• Bulk operation: 50+ records or files
• Production environment: tagged prod, production, live
• No rollback path: no backup, no soft-delete
• Sensitive data: PII, payment info, credentials
• Chain reaction: this step triggers other critical steps

After Checkpoint Resolution

User approves:

1. Execute the action
2. Report result briefly: Completed: [what was done]

User rejects:

1. Do not execute the action
2. Suggest alternatives: safer path, partial operation, dry-run
3. Wait for the user to set a new direction

Audit Trail

Log every checkpoint decision throughout the task:

[CHECKPOINT LOG]
Step     : [step number or sequence]
Action   : [summary]
Risk     : LOW / MEDIUM / HIGH
Decision : Passed silently / Approved / Rejected

At the end of every task, show the complete checkpoint log summary to the user. This is mandatory — never skip the audit trail.

Guardrails

• Never skip HIGH RISK checkpoints — no exceptions, even if the user previously said "approve all."
• When in doubt, escalate — if risk level is ambiguous, choose the higher level.
• Always suggest alternatives for HIGH RISK actions — give the user a safer path.
• Audit trail is mandatory — even LOW RISK actions must be logged silently.
• Respect explicit user intent — if the user clearly states "I know the risks, proceed," honor it for that specific action only (not blanket approval).
• This skill applies to every agent action — it is not opt-in per step.

Examples

See references/EXAMPLES.md for worked examples across all risk levels.

Templates

• Use templates/checkpoint-high.md.tmpl for HIGH RISK checkpoint format.
• Use templates/checkpoint-medium.md.tmpl for MEDIUM RISK checkpoint format.